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Holiday Rentals in Key West, FL

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    297 Holiday Rentals in Key West
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    ₹18,708
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    1 / 19
    4.5 of 5 stars (37) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ₹109,129
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    1 / 11
    5 of 5 stars (40) Excellent
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    ₹205,787
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    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    ₹335,059
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    1 / 17
    5 of 5 stars (2) Excellent
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    ₹155,899
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    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    ₹17,149
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
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    • Gym
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    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling,... View all property information
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    ₹155,899
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    Overview Reviews (2)
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    • Dryer
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
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    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - THE STUDIO AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located... View all property information
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    5 of 5 stars Reviewed 11 February 2015
    I've been to Key West many times and know the city as well as my home town. First, the most important thing is LOCATION. You want to be within walking or biking of all the...
    5 of 5 stars Reviewed 2 September 2014
    I really enjoyed my stay at the sailmaker's studio. The staff as well as the owner were very easy to work with and very helpful. My small dog was with me and he enjoyed it too. It...
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    ₹21,764
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    1 / 18
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (3)
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    • Balcony
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    • Internet Access
    • Ocean Views
    • Shared Outdoor Pool...
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    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. Please search for or see Key West Yacht and Breakfast for more information. Otherwise, the system only allows you and us to converse via the online system and will block any attempts to send phone numbers, etc.... View all property information
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    5 of 5 stars Reviewed 10 March 2015
    We enjoyed our visit and stay. The Marina and boating way of life is slow and relaxing which is exactly what we were looking for. The boat was as advertised and we found it clean...
    5 of 5 stars Reviewed 6 March 2015
    The owners of this property were helpful in so many ways. I feel they went above and beyond to help us out with a lot of questions about Key West and activities that we were...
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    ₹174,607
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    1 / 48
    Overview
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    • Air Conditioning
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - THE TREETOP APT AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Apartment for Two - Incredible Location in Historic Old Town Gorgeous one bedroom apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental... View all property information
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    ₹155,899
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    Overview Reviews (1)
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
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    About this property
    This vacation home is only licensed for stays of 28 nights or more. Southard Square Hideaway is a newly renovated first floor corner condo perfect for 2 plus space for visiting friends and family! Monthly Rental A surprise awaits you inside the gates of the Southard Square village. Nestled in the... View all property information
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    ₹249,439
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    1 / 14
    5 of 5 stars (8) Excellent
    Overview Reviews (8)
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Private Outdoor...
    • Washer
    • Wi-Fi
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    About this property
    THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from... View all property information
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    4 of 5 stars Reviewed 23 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    5 of 5 stars Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised however...
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    ₹18,708
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    Overview Reviews (14)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    3 of 5 stars Reviewed 8 April 2014
    The house is as described. Clean and comfortable. The condo is very pleasant and safe. Pool was very much appreciated by our children. The main inconvenient is the noise. The...
    4 of 5 stars Reviewed 20 April 2013
    We enjoyed our stay and will plan to come again. The only complaints we had was that the lower bedroom dresser had the bottoms missing out of two drawers so unpacking the suitcase...
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    ₹109,129
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    1 / 13
    4.5 of 5 stars (41) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (41)
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    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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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    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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    ₹636,069
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    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (8)
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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    5 of 5 stars Reviewed 10 March 2015
    We loved our stay at Catherine St. The home is set up with everything that you could ever need. The pool is very private. Skinny Dipping a definite. All of the furniture is custom...
    5 of 5 stars Reviewed 27 February 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
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    ₹324,270
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    1 / 13
    3.5 of 5 stars (3) Average
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
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    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly... View all property information
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    5 of 5 stars Reviewed 18 June 2009
    We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful...
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    ₹218,259
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    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas.... View all property information
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    5 of 5 stars Reviewed 4 May 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    ₹324,270
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    Overview Reviews (3)
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park... View all property information
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    5 of 5 stars Reviewed 26 September 2014
    We felt grateful to have the opportunity to experience this historic home in Key West. It is conveniently located to restaurants and attractions. The home itself is beautifully...
    5 of 5 stars Reviewed 20 July 2014
    We were delighted when we entered this lovely house. Very "Key West," just what we were looking for. The house was clearly updated with high-quality finishes and in impeccable...
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    ₹109,129
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    Overview Reviews (55)
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    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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    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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    4.5 of 5 stars (65) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (65)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
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    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. Any reservation obtained under false pretense will be subject to eviction... View all property information
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    4 of 5 stars Reviewed 7 April 2015
    This was our first stay in Key West and at first we were uncertain of this location since it is actually on Stock Island. It turned out to be the best place for our needs. The...
    5 of 5 stars Reviewed 7 March 2014
    We had a wonderful time at this condo. The Condo was very large and comfortable. We were around a small corner from the elevator which really helped since I was the youngest at...
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    ₹193,315
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    1 / 1
    Overview
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    • Air Conditioning
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    • Pets allowed
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    About this property
    Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony... View all property information
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    1 / 10
    4.5 of 5 stars (34) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (34)
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    • Air Conditioning
    • Balcony
    • Gym
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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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    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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    ₹243,203
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Overview Reviews (1)
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    • Safe
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    • Pets allowed
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    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the... View all property information
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    5 of 5 stars Reviewed 1 March 2014
    This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded all...
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    ₹361,686
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    4 of 5 stars (2) Very good
    Overview Reviews (2)
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    • Air Conditioning
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    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
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    About this property
    30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated 'Conch' house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden... View all property information
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    3 of 5 stars Reviewed 18 June 2009
    Packer retreat is a great house. So great I am renting it in 2010. The layout and outdoor space is unusually large for Key West. And the home is very private and quiet. the...
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    ₹13,719
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    • Safe
    • Satellite TV
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    • Washer
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    • Pets allowed
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    About this property
    What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet.... View all property information
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    5 of 5 stars Reviewed 7 March 2015
    We spent 3 nights on this boat. James the owner was easy going and welcoming. He explained all we needed to know and was available by phone for any questions or concerns. Boat...
    5 of 5 stars Reviewed 3 March 2015
    For sail boat minded people this is perfect : comfortable boat, beautiful yacht club and possibility to enjoy environment with kayaks. After visit of crowded key west it's very...
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
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    • Pets allowed
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    ₹28,062
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    1 / 15
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (8)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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    4 of 5 stars Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 30 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    4.5 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
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    5 of 5 stars Reviewed 9 March 2015
    I stayed at the place with 6 girl friends. It was one of my favorite vacations yet. All ages 24-27. Tyler was just a great help and worked with us to get the condo booked. He also...
    4 of 5 stars Reviewed 9 April 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    ₹6,236
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    1 / 27
    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • 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 Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright... View all property information
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    5 of 5 stars Reviewed 18 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    ₹31,180
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    • Air Conditioning
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    • x
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    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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    5 of 5 stars Reviewed 22 August 2013
    This was an excellent location, rooom and staff for a week or more stay. We enjoyed it.
    4 of 5 stars Reviewed 12 July 2013
    Docking & unit satisfactory.
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    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
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    ₹16,837
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    About this property
    Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees.... View all property information
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    5 of 5 stars Reviewed 26 September 2012
    Our recent stay at Vista Fresco was great. Everything we needed from the blender to extra bath towels was provided. The only issue was something that management could do nothing...
    2 of 5 stars Reviewed 5 July 2012
    We stayed at Vista Fresco in March, 2012 with our 9 & 11 year-old children for Spring Break. I feel like we were mislead about the property in some respects, and we didn't feel...
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    5 of 5 stars (3) Excellent
    Overview Reviews (3)
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
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    5 of 5 stars Reviewed 19 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed 3 March 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    • Suitable for children
    • x
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    • ?
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    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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    4 of 5 stars Reviewed 8 July 2014
    We had a large group visiting Key West for the Swim Around Key West annual event. We had plenty of space for all 10 of us to sleep comfortably. The washer and dryer were very...
    4 of 5 stars Reviewed 19 June 2013
    Had 7 friends stay in the St. Kitts for a long weekend. Rooms were great - there was a lot of space for all of us, with plenty of bathrooms (4), balconies, kitchen, etc. Never...
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    4 of 5 stars (9) Very good
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    • x
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony... View all property information
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    5 of 5 stars Reviewed 5 December 2012
    112 Beach Club is a large 2b/2b condo right on the atlantic! The complex is a secure property with very nice amenities. This condo itself is a bit dated, but was very clean and...
    2 of 5 stars Reviewed 3 February 2012
    It was a nice condo, accommodating my wife and I and another couple vacationing with us, but it was dirty. The refrig and appliances were not cleaned, the home was pretty much...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Gym
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
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    4.5 of 5 stars (32) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Suitable for children
    • x
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    • ?
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    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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    4 of 5 stars Reviewed 19 September 2013
    Relaxing fun time with friends. Rented beach cruisers and saw the island.
    5 of 5 stars Reviewed 19 July 2013
    Excellent friendly,clean, lots of linen and supplies. Rooms large and very cozy. loved the balconies and outside furniture. Everyone had smiles on their faces,it made you feel...
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    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed... View all property information
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    5 of 5 stars Reviewed 17 January 2013
    The apartment was great overall. Very spacious and clean and there was a lot provided that I did not expect (ie batteries, beach towels, beach bags, fishing pole, coolers etc...
    4 of 5 stars Reviewed 11 May 2012
    We rented this on recommendation from trip advisor...it was a lovely as it was described. The beds were fantastic!!! The furniture comfortable for a vacation house. Linens...
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    4.5 of 5 stars (27) Very good
    Overview Reviews (27)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • 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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    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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    4.5 of 5 stars (37) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (4)
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    • Suitable for children
    • ?
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    About this property
    Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family... View all property information
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    2 of 5 stars Reviewed 15 April 2014
    We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
    5 of 5 stars Reviewed 10 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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    4.5 of 5 stars (8) Very good
    Overview Reviews (8)
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    • Grill
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    • Pets allowed
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    • Suitable for children
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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    4 of 5 stars Reviewed 26 March 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
    5 of 5 stars Reviewed 6 March 2015
    Located in a private condo complex, the unit we stayed in featured excellent amenities while also clean and well maintained. Location to old town and Duval will require...
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    ₹9,292
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    • x
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    About this property
    The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately... View all property information
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    5 of 5 stars Reviewed 14 October 2014
    My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
    5 of 5 stars Reviewed 12 August 2014
    My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
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    ₹13,719
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    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. 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. Within 2 blocks you'll find Key West... View all property information
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    4 of 5 stars Reviewed 7 March 2015
    My husband and I have made numerous trips to Key West and have usually stayed at larger hotels but this time we wanted to try something different so we booked the Bali Hideaway...
    5 of 5 stars Reviewed 13 March 2013
    This is the first time my husband and I have been to Key West and this was the perfect spot to stay. It was just the right size for a romantic getaway. Even though we were only a...
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    4 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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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    4 of 5 stars Reviewed 10 March 2014
    Traveled with wife and brother and his wife. Very clean, nice size 1200 sf, convenient layout, Pool was nicely heated, adequate parking. about 3/4 of a mile from Malory Square...
    4 of 5 stars Reviewed 11 July 2013
    The condo was nice, a few updates are in order. More cooking untesils and cookware would be nice. Overall, clean, nice location, friendly neighbors and friendly and helpful...
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    4 of 5 stars (30) Very good
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    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and... View all property information
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    5 of 5 stars Reviewed 18 April 2014
    This house will not be for everyone. It's rustic, and advertised as such. If you like new, bright, cookie cutter houses with granite countertops and pillowtop mattresses, with...
    5 of 5 stars Reviewed 22 August 2012
    The house was even more perfect than we'd imagined. It perfectly captured the Key West charm that we wanted while visiting. The backyard was amazing and we enjoyed the pool and...
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    4.5 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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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    5 of 5 stars Reviewed 18 July 2013
    I used to live in Key West and have had friends stay here before. I was excited to see the new renovations they had done. The room was beautiful and clean and our stay was great...
    4 of 5 stars Reviewed 2 November 2012
    We had a corner 2bed unit that was spacious. Kitchen was well equipped to accommodate 8. Helpful advice from office.
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    4.5 of 5 stars (26) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • 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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    4 of 5 stars Reviewed 25 January 2014
    Nice location looking out on Garrison Bight Marina and close enough to Old Town. Super spacious unit was very nice and clean. Completely equipped and has washer/dryer stack. A...
    3 of 5 stars Reviewed 29 July 2013
    Great location especially if you bring a boat.
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    5 of 5 stars (12) Excellent
    Overview Reviews (12)
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    • Suitable for children
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    About this property
    SeaShadows is a townhouse located just 2 blocks from Duval Street and a few minutes walk from Mallory Square. Down the street is Ft. Zachary Taylor Park where you can spend the day fishing, swimming, barbecuing, walking, and anything else that you can think of doing in the sun. It sleeps 4... View all property information
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    5 of 5 stars Reviewed 3 April 2015
    First of all, I had no idea of all the amenities this offered. I was floored when I got in! I mean it, towels, robes, shampoo, toiletries, anything that you normally pack could...
    5 of 5 stars Reviewed 1 July 2013
    The house was very nice and well kept and within walking distance to just about anything. We did a lot of walking and actually ate in most of our meals.
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    ₹433,400
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    About this property
    SPRING SPECIALS! 15% off MAY 2015! Please see Specials Page for terms, rules and limitations. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco... View all property information
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    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.