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Holiday Rentals in Key West, FL

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    All 483 Rentals in Key West
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    Travellers to Key West are booking December dates now. Secure your holiday home today, and have the perfect trip.
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    ₹15,967
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    1 / 12
    4.5 of 5 stars (60) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    ₹12,774
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    1 / 21
    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    ₹69,298
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    1 / 27
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    ₹18,394
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    1 / 27
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    Key West, Florida Keys 33040
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    ₹16,287
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    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (14) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 28 May 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed 30 March 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    ₹114,965
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It... View all property information
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    Key West, Florida Keys 33040
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    ₹19,161
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    1 / 10
    4.5 of 5 stars (34) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (34) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 30 October 2014
    Nice two bedroom condo, well furnished, great location. Would definitely stay here again. Becky and her staff at the rental company were a pleasure to work with.
    4 of 5 stars Reviewed 25 June 2013
    BMW Fantasy was an excellent vacation rental. While a little dated, the pictures of the unit don't do it justice. It was clean, well kept and super convenient. Outside of the...
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    ₹95,804
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    1 / 14
    4.5 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (12) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Eaton Manor sits on the north side of LaBrisa and provides easy access to... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 14 May 2013
    Overall the condo is very nice. Towels and sheets could use an update along with all of the kitchen amenities. Mainly pots, pans, silverware etc. overall the place worked out...
    2 of 5 stars Reviewed 4 April 2013
    First off, we are not the type of people looking for a 4star place on a beer budget, then trash the accommodations on trip advisor because a lamp was out or the water tasted...
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    1 / 10
    4 of 5 stars (55) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (55) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 28 April 2014
    Our rental was clean, with plenty of supplies and towels. It was in a gated area and we always felt very safe. I loved sitting on the patio outside, enclosed by foliage so it...
    5 of 5 stars Reviewed 2 September 2013
    It was close to walk to Duval Street and short drive or walk if you like to Fort Zachary Taylor state park for swimming at the beach.
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    1 / 15
    4.5 of 5 stars (37) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (37) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 13 August 2013
    Lobster Fest was a blast! We had a great time and loved being on Duval Street, but far enough away from the main strip. The property was nice and well kept. Bathroom shower...
    4 of 5 stars Reviewed 20 June 2013
    Property is OK. Needs some maintenance and upgrades but overall acceptable, but not great. Good location if you want to be on Duval Street but away from the noise. Includes a...
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    1 / 13
    4.5 of 5 stars (41) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (41) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony on the 2nd floor deck. In case you would like to work on vacation the unit has a wireless DSL connection. There is one assigned parking space per unit.... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 22 May 2014
    In last year's review, I said I would unhesitatingly stay here again. I did. And was far less charmed. I do love the Truman Annex location and the design of the condo. The...
    5 of 5 stars Reviewed 19 June 2013
    very nice place in excellent location
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    1 / 11
    5 of 5 stars (40) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (40) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 25 June 2013
    Stayed at the Shipyard 253 and had a wonderful time. Very nicely decorated, comfortable and a great location - just 2 blocks from Duval St. I would stay there again!
    5 of 5 stars Reviewed 31 May 2013
    Great central location. Walking distance to most things of interest. Liked the fact it's a Gated community with assigned parking place. Not beach front, but that wasn't important...
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    ₹22,354
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    1 / 19
    2 of 5 stars (1) Poor
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 19 May 2015
    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels...
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    ₹6,387
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    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Key West has all of the charms of being away from the world, yet with all of the worldly conveniences near at hand. Located in the historic old town, Namaste Key West is in a quiet residential neighborhood, with beaches 5 minutes away, 3 yoga studios within a block, coffee shops, and a grocery... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 September 2014
    My husband and I stayed in lovely Namaste from May 15th through Aug 15th and were enchanted the entire time. The house is lovely, even better than the fabulous pictures. It is...
    5 of 5 stars Reviewed 30 April 2013
    The Namaste Cottage was an amazing place to stay during our time in Key West. We spent two weeks at Namaste and were constantly reminded of how central it is to all of the great...
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    ₹38,322
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Key West, Florida Keys 33040
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    1 / 21
    4.5 of 5 stars (28) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (28) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 9 May 2013
    Great place for singles And families. Easy access to entertainment and even Publix, Walgreens, restaurants everything! staff great, Highly Recommend! gorgeous view
    1 of 5 stars Reviewed 30 April 2013
    We have been going to Pelican Landing for the past several years. This has been the best experience so far. Any concerns we had were addressed immediately and the pool looks great...
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    4.5 of 5 stars (27) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (27) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 25 January 2015
    We were pleased with the spacious accommodations at the Harbor Island Retreat. The rooms were clean and they (and view) were as depicted on the TA web site. The unit was...
    4 of 5 stars Reviewed 28 November 2014
    Not close to Duvall Street where everything is happening bit we enjoyed it and the unit was nicely decorated and had everything we needed. Huge balcony overlooking pool with a...
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    ₹12,646
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    1 / 10
    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The Bonaire Suite is a bi-level suite decorated in a rich contemporary Palm Tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door. Downstairs is a living room with sofa which converts to a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 12 July 2014
    My friend and I stayed at the Bonaire Suite and it was perfect! Cute bungalow style with plenty of room and amenities. So close to Duval, but you couldn't hear the roar, which...
    5 of 5 stars Reviewed 13 June 2014
    Perfect location! Half block from Duval street. Very cozy and well equipped and lovely pool area. I highly recommend this place.
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    ₹13,732
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    1 / 25
    4.5 of 5 stars (43) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 13 May 2015
    We loved Ann Street Gardens! A block from Duval 2 blocks from the historic seaport. In the middle of it all but as quiet as can be! The gardens, the pool, the home, all...
    5 of 5 stars Reviewed 6 November 2014
    My wife and I wanted a private getaway and the Ann Street house was just what the doctor ordered. The place was immaculate and just as important; quiet. We stocked the fridge...
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    ₹15,329
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    4.5 of 5 stars (47) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 2
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    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 3 July 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    5 of 5 stars Reviewed 2 August 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 April 2015
    Had a fantastic holiday in the Bimini Suite. It was clean, well decorated and probably had the most comfy bed I've ever slept in whilst away from home. The garden area was lovely...
    5 of 5 stars Reviewed 17 March 2015
    Stayed in the Bimini Suite with 2 friends . My wife made the reservations and dealt directly with Evelyn and David who were always reachable and friendly . You will not regret...
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    4.5 of 5 stars (24) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 25 March 2015
    Had a great time in Key West and this place made it all possible! First of all, it is within a block or two of Duval St. Staying that close was important to us because we wanted...
    5 of 5 stars Reviewed 24 October 2012
    We loved this place. We travel with out camper but thought staying in old town would be a good choice. We were right. We stored the camper and parked the van (one of the few...
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    ₹287,411
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
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    Key West, Florida Keys 33040
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    ₹312,959
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    4.5 of 5 stars (15) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 April 2014
    We rented this 4 bedroom 3 bath house for vacation with our adult children, 6 month old grandson and 87 year old father. It was perfect! One bedroom downstairs for Grandpa, a...
    5 of 5 stars Reviewed 11 March 2014
    We loved the privacy and security of the house. All family members enjoyed the quiet time at the house and the party atmosphere within walking distance. We had day trips and...
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Dryer
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    • Hot Tub
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
    • x
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    About this property
    RENTAL RATES ARE NEGOTIABLE ......please contact us for current pricing and availability (we do not maintain calendars) In the event you, or your family, your guests, or your friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 July 2014
    My husband & I found the Conch House online. The property manager, Craig, met us upon our arrival and was very friendly. Throughout our trip, he was very helpful and very...
    5 of 5 stars Reviewed 22 June 2014
    This property is so beautiful and peaceful.!! Perfect location, 2 short blocks from Duval, 1 block from Ft. Zach beaches. We stayed in the Conch House , We could not have been...
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    4.5 of 5 stars (11) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
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    • Dryer
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    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 15 April 2015
    Truman House was a joy! Location was perfect - convenient to everything. Pool was wonderful. Lots of living space - front porch, back deck, living room and a nice gathering...
    5 of 5 stars Reviewed 14 April 2015
    We are frequent visitors to Key West, where we usually get a tiny hotel room and spend all of our time out of the room. For a special occasion, we brought the kids, spouses, and a...
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
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    • Elder access
    • x
    About this property
    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the... View all property information
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    Key West, Florida Keys 33040
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    1 / 18
    5 of 5 stars (5) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    • Air Conditioning
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    • Shared Outdoor Pool...
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    • Pets allowed
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    • x
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    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 May 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places and...
    5 of 5 stars Reviewed 26 May 2015
    It was a fun and unique vacation! At first it took some getting used to, flushing the toilets, water supply, close quarters, etc. But by the end that's what made it memorable. The...
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (7) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 15 May 2015
    Strongly recommended for families, very nice backyard, private pool that you cannot get your children out of it, perfect location. But beware of mosquitos at the evening...
    5 of 5 stars Reviewed 28 April 2015
    I've been going to Key West for the past 10yrs, and have stayed all over the island. I was looking for a place for a long weekend (sometimes hard to come by in EYW bc lots of...
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    ₹351,281
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    4 of 5 stars (5) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 25 November 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St. Everything...
    5 of 5 stars Reviewed 7 February 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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    3.5 of 5 stars (9) Average
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 4 March 2015
    The property could use some updating. A little paint and some updated furniture would do wonders. Towels without rust and bleach stains should be considered. But we are used to...
    3 of 5 stars Reviewed 15 December 2014
    My family (a group of 9) stayed here for a week while in Key West for a wedding. Amelia's Hideaway was...ok. The rooftop deck and poolside patio were perfect for sitting outside...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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    Key West, Florida Keys 33040
    From
    ₹76,643
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    1 / 21
    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (8) Make Enquiry
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
    • x
    About this property
    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 24 January 2015
    While the Artist Cottage was not available, the owner had another Shipyard condo that was perfect for us. The property is nicely maintained, the pool clean and warm, and the...
    5 of 5 stars Reviewed 30 June 2014
    Wonderful location was able to walk to experience Key West. Something for everyone to enjoy with 2 older teenagers. Did something every day but was very relaxing, never felt...
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    ₹319,346
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 23 December 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and easy...
    5 of 5 stars Reviewed 2 November 2013
    Really enjoyed the comfort of the unit. Close to everything but no need to leave!
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Balcony
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    • Internet Access
    • Ocean Views
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
    From
    ₹287,411
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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    • Suitable for children
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    About this property
    History buffs love to immerse themselves in the centuries old legends of Key West – and if they’re lucky, they’ll find room in Smuggler’s Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the island. Smuggler’s Den, a delightfully... View all property information
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    Key West, Florida Keys
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    ₹22,929
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    1 / 24
    4.5 of 5 stars (33) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Sauna
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 28 May 2015
    Depending on why you are going to Key West, this is an excellent choice. The apartments are fabulous and well decorated with everything you need. It is close enough to the...
    5 of 5 stars Reviewed 26 March 2015
    Great value for money. I am not a hot tub fan so this was not important to me. The weather did not cooperate but this did not matter as we were having such a great time.
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    ₹332,120
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    1 / 25
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • ?
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing... View all property information
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    Key West, Florida Keys 33040
    From
    ₹18,458
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    4.5 of 5 stars (7) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (7) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
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    • Hot Tub
    • Housekeeping...
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    • ?
    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 24 April 2015
    Cute two story Key West cottage. Located blocks away from Duval, but yet quiet. Good times were had at the Jacuzzi and the top patio. The swing on the top balcony was nice and...
    5 of 5 stars Reviewed 9 July 2014
    I went down to Key West with my husband, 2 year old son, and baby sitter. This cottage was perfect for us. The bedrooms (both upstairs) were comfortable and both had great...
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    ₹10,794
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    5 of 5 stars (20) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 13 February 2015
    Atlantis House is a very special hideaway. It is called a guest house, and we were truly the guests of Steve and Kayla. They were so welcoming from the day we arrived: helping...
    5 of 5 stars Reviewed 1 December 2014
    Steve, and Kayla, our Hosts, met us when we arrived, and from that moment on we felt like we were visiting family. Our room was immaculat , well appointed and warm. Kayla prepared...
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    ₹16,478
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    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Pets allowed
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    • x
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    About this property
    Part of TROPICAL VILLAGE Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    ₹20,119
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    1 / 15
    4.5 of 5 stars (10) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (10) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Make our lovely home your dream vacation destination in fun-filled tropical Key West, Florida. '1800 Atlantic' is Key West's premiere luxury condo complex on a private Atlantic Ocean beach. Our beautifully furnished large 2 bedroom and 2 bath condo overlooks a serene tropical garden. Both... View all property information
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    Key West, Florida Keys 33050
    5 of 5 stars Reviewed 17 March 2015
    Patrick was excellent. He responded to emails quickly. There were no extra charges. The location was just as described in a secure building. The condominium was very clean...
    5 of 5 stars Reviewed 17 February 2015
    We had a wonderful week at 1800 Atlantic. Patrick was a pleasure to deal with and was responsive to all our questions. The unit was in excellent condition. I was not prepared...
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    ₹14,051
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    About this property
    The 'SeaJay' at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 22 May 2014
    We enjoyed our week in the condo immensely. I considered it a bargain compared to other vacation rentals we checked. There were 5 of us (3 generations) and there was plenty of...
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    ₹24,143
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    5 of 5 stars (13) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    3 of 5 stars Reviewed 13 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
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    ₹15,265
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    4.5 of 5 stars (7) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    About this property
    Beautifully remodeled, 1374 sq. ft., 2 bedrooms (both are King Beds) 2 Bath condo located on the beach in a resort complex -(SLEEPS 6). Gorgeously landscaped & located RIGHT NEXT TO SMATHERS BEACH, the largest beach in Key West! AMENTIES INCLUDE: Private 40' Balcony, Master suite, Resort... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 March 2015
    This is a nice complex and the unit was very nice. If you like a quiet area of Key West this is it. It is really to far from the old town area to walk and parking in Key West is...
    5 of 5 stars Reviewed 7 January 2014
    I traveled with my wife and 4 teenagers. The best part about this condo was its location...It was a short walk to Smather's Beach in one direction, and 1 mile from Duval St. in...
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    ₹32,446
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    3 Bedrooms / 3 Bathrooms / Sleeps 10
    traveller have booked this property
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    Amenities & Details
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This nightly group rental consists of 3 separate units. 1) Porchside Paradise 2) Orange Blossom Suite 3) Deckside Suite . Three separate bedrooms with queen sized beds. Two sleeper sofas and two private hot tubs! Located at 510 Petronia St, literally steps from Duval St! Take advantage of the... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    ₹15,201
    / Night
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    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Hot Tub
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of Conch Republic Cottages 'Porchside Paradise' is located in the front section of the 'Conch Republic Cottages'. This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 22 April 2015
    My 1st visit to Key West was in 1971 when it was a small, end of the road, sleepy beach town with old homes & history. Things have changed & it has grown tremendously. One thing...
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    From
    ₹38,322
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Gym
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Price includes taxes. cleaning fee and sunset sail (weather willing). For six or less adults only. You have the use of three of four private cabins each with its own marine style bathroom and queen like bed. Captain Charles and wife Deborah use one cabin.The 'ANAA B' is 41ft long and 24ft wide... View all property information
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental Accommodation on Key West

    The diversity of the holiday rental accommodation available on Key West means that there is something available to suit every budget and surely all tastes. From cottages and modest condos, to villas and townhouses, to penthouses and country estates, Key West has it all, meaning that your holiday in Key West can be as free of restriction as possible, at a price you can afford. If you want the freedom to explore Key West at a time and in a manner of your choosing, selecting the holiday rental best suited to your individual requirements is the way to achieve your goal.

    Water sports in Key West

    The weather and geography of Key West make it an ideal location for a great many different types of water sports. Fishermen of all disciplines can choose from the art of fly fishing for tarpon, to deep sea fishing expeditions from a boat and most options in between. Those simply interested in being out on the water can go pleasure cruising on a charter boat, perhaps to view the dolphins and other marine life, hire a kayak and meander through the waterways at their own pace, or even jump on a jet ski and enjoy some high speed thrills. Scuba divers can admire the natural coral reefs or explore the wrecks in the area, some of which were deliberately sunk to form artificial reefs.

    Popular attractions in Key West

    The beaches of Key West are both numerous and beautiful but a visit to the Fort Zachary Taylor State Park allows you to combine your beach relaxation and activities with an inexpensive tour of the fort, or perhaps a casual stroll along one of the nature trails. Art lovers will find a great many galleries of interest in Key West, with the majority local to the popular Duval Street part of town. Key West Golf Club is not only about allowing golf lovers to practise their swing, it also has a popular restaurant and bar, which could perhaps serve as a point at which non-golfers can arrange to meet players after their round. One monument not to miss in Key West is the small round landmark which denotes the most southerly part of the continental United States.

    Restaurants and bars in Key West

    Duval Street is the popular centre of Key West in so many ways, not least when it comes to restaurants. When you are eating out from your Key West holiday rental of an evening, you may wish to sample popular outlets such as Nine One Five or Mangoes, or try the Banana Café for breakfast or lunch. Blue Heaven in the Bahama Village is the place to sample outdoor dining of the highest quality, with an indoor option available if preferred. The bars and clubs of Key West are plentiful in the extreme, with options to suit all tastes and requirements and allow you to party the night away in style.