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Holiday Rentals in Key West, FL

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₹235,221
Per Month
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1 / 15
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
₹19,189
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1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 7
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₹9,780
Per Night
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1 / 27
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1 Bedroom, 1 Bathroom, Sleeps 4
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₹13,928
Per Night
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1 / 27
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (47) Make Enquiry
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  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room.The entire property has been decorated using art from the local galleries and artists. The theme is 'Key West' from scenes around the area including... View all property information
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5 of 5 stars Reviewed 21 September 2014
Great vacation spot in Key West. The condo was much larger than expected. We did not realize that the bedrooms are upstairs. You do have to park and walk up stairs to enter the...
4 of 5 stars Reviewed 2 August 2014
Stayed here for a week and it was great. Perfect location. TV in second bedroom didn't work. But everything was very clean. Late check in worked perfectly. Had everything we...
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₹359,022
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1 / 11
3 Bedrooms, 4 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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₹129,991
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1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
BOGEY'S RETREAT: Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment. If you're a golfer, this house is ideal since... View all property information
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₹16,589
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1 / 30
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
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5 of 5 stars Reviewed 25 June 2014
Had a great time staying in this condo with 4 of my besties! We enjoyed having plenty of space...upstairs and downstairs, 2.5 baths...great for 5 women! The location of the...
5 of 5 stars Reviewed 16 April 2014
This is a fantastic complex and is managed/owned by Rick who will go out of his way to make you happy. He picked us from the airport, fishing and back in his Escalade at no...
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₹340,452
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1 / 36
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
28 NIGHT MINIMUM STAY REQUIREMENT - SOUTH STREET SERENITY Beautiful Vacation Home just steps from the Beach! This light and airy 3 bedroom, 2.5 bath home has a wraparound Bahamian Style deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private... View all property information
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4 of 5 stars Reviewed 29 April 2014
the service we received from Carlos the property manager from south street serenity was excellent. whenever we had a question he either answered the phone or called us back...
5 of 5 stars Reviewed 7 June 2014
Von der ersten Sekunde an haben wir uns sehr wohl in diesem tollen, gemütlichen und wunderbar eingerichteten Haus gefühlt. Das Haus bietet alles, was man braucht, nein, es bietet...
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₹129,991
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1 / 33
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States.This lovely 2 bedroom 1.5 bath townhome is freshly painted and newly furnished. Enter the open and airy living space... View all property information
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3 of 5 stars Reviewed 12 December 2013
The house was great Loved being on the golf course very quite area great pool Security was very nice and helpful The staff: At home was great Libby is the best
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₹24,760
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1 / 25
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
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5 of 5 stars Reviewed 8 June 2011
This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
5 of 5 stars Reviewed 5 March 2010
The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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From
₹11,452
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1 / 8
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Pool Table
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which will help make your stay in Key West special. It is located in a wonderfully private... View all property information
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5 of 5 stars Reviewed 9 December 2014
This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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From
₹21,603
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1 / 18
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Ocean Views
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
FOR INSTANT PRICING, go to KeyWestYachtandBreakfast.com. Most nights require 3 night minimum but email or call us if you want less and we can negotiate a fair rate. Upscale 'Yacht and Breakfast'! 3 bedroom, 4 bed, 2ba luxury yacht. Fully equipped from bow to stern -- Galley (kitchen to the... View all property information
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5 of 5 stars Reviewed 12 January 2015
It never crossed my mind to look into staying on a Yacht in Key West. Now, everywhere we travel it is our first option. The boat accommodations were perfect for us. We could fish...
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₹8,542
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1 / 24
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southernmost Sanctuary Suites The Osprey Suite (Formerly the Osprey Suite) - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a... View all property information
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5 of 5 stars Reviewed 28 August 2014
This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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₹222,841
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1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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₹17,889
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1 / 18
1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Eyebrow House is a very spacious one-bedroom suite with a large front porch and palm tree-filled private fenced-in yard overlooking a quiet side street. Our guests enjoy the best of both worlds as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a half block away.... View all property information
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From
₹13,494
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1 / 27
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Details Reviews (22) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Southernmost Retreat 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. The perfect place to listen to your favorite music while... View all property information
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4 of 5 stars Reviewed 23 January 2015
We just spent a week at SMR and really enjoyed our stay! Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
4 of 5 stars Reviewed 23 November 2014
Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub which...
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From
₹16,713
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1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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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₹12,875
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1 / 28
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Details Reviews (24) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
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5 of 5 stars Reviewed 18 February 2015
SEA BREEZE was great we were a block away from the 90miles to Cuba attraction. it was really close to little beach "south beach" it was very clean and had 1 parking spot just...
4 of 5 stars Reviewed 7 February 2015
For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
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From
₹16,589
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1 / 33
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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5 of 5 stars Reviewed 15 January 2015
My husband and I stayed here with another couple and it was great! Great location, lots of room! There is definitely a master suite and a second bedroom but both rooms have...
5 of 5 stars Reviewed 13 January 2015
Townhouse was nice,clean,stocked well and as promised .the location was great...walking distance to everything we wanted..quiet..pool was well kept, rental company was accessible...
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₹210,461
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1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights,... View all property information
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From
₹18,570
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1 / 22
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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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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From
₹14,237
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1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse... View all property information
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₹16,589
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1 / 26
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
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5 of 5 stars Reviewed 5 June 2014
Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
4 of 5 stars Reviewed 17 April 2014
The location was good. Not far from Duval. It was very clean. I really enjoyed the hot tub on the patio. The beds were so comfortable :)) Unfortunately a car was parked in front...
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₹11,637
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1 / 23
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The kitchen offers an under-counter fridge, microwave, coffee maker, toaster, blender and everything to cook, prepare and enjoy a light meal…and don’t forget the BBQ grill and Ice-maker by the pool! This very comfortable unit also has a very sexy two-person custom shower with glass door,... View all property information
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5 of 5 stars Reviewed 30 June 2014
The unit was clean and in a great location. Maintenance was attentive and cleaning staff also. The only trouble we had was virtually ever night some giant vehicle was running...
5 of 5 stars Reviewed 4 April 2014
The place we stayed at was small inside, but big on the outside space. The courtyard was beautiful and added another dimension to the space. Like a living room in the tropics!
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₹430,207
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1 / 21
3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
Save 3% off published rates if you pay by cash/check. 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 Steamplant at water's edge has been... View all property information
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From
₹12,875
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1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
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5 of 5 stars Reviewed 6 January 2015
You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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From
₹11,637
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1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete... View all property information
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4 of 5 stars Reviewed 18 February 2015
My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent selection...
5 of 5 stars Reviewed 2 September 2014
I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
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From
₹12,256
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1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
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5 of 5 stars Reviewed 28 January 2015
We stayed here once back in 2001. The place hasn't changed. That's good and not so good. Good because the facility met our needs for a short stay to participate in the Key West...
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From
₹8,542
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About this property
The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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4 of 5 stars Reviewed 16 January 2015
This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and walk...
5 of 5 stars Reviewed 17 November 2014
We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a long...
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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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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Water Views
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • 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, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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About this property
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit opens to the living room,... View all property information
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3 of 5 stars Reviewed 20 January 2015
Overall was okay. Some details that were lacking made the stay not quite as good as expected for the cost. TV was small. Guest BR bed was not comfortable. There was mold on...
5 of 5 stars Reviewed 2 November 2013
Very attractive, well located, and with so many nice little extras. The managers are attentive and very helpful. It's easy to tell that a lot of thought and care go into keeping...
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
Welcome to Artist House: a 2 bedroom 2.5 bath rooftop townhome located within the gated community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located so that you can park your car in the... View all property information
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5 of 5 stars Reviewed 11 November 2014
My husband and I have rented this unit twice now and it is the perfect place. The rental company is wonderful to work with try to get you in to the unit early if possible. This...
4 of 5 stars Reviewed 5 August 2014
Nice condo right on duval st. Good location for a more quiet stay.Cvs right around the corner Rooms where nice. Hot tub on patio is a plus. Only negative comment is I wish we...
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  • Suitable for children
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About this property
Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the... View all property information
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5 of 5 stars Reviewed 17 October 2014
We had an excellent experience staying in this studio for our honeymoon. Only drawback was the lack of kitchen equipment which made it difficult to cook a full meal for...
4 of 5 stars Reviewed 25 September 2014
It was a great location out of the way but by everything. Also the room was very secluded to the back of the property for a nice romantic time.
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Elder access
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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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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Elder access
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About this property
Part of Southernmost Sanctuary Suites The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee... View all property information
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4 of 5 stars Reviewed 28 July 2014
Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each morning...
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Shared Outdoor Pool...
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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
Part of 4 exclusive units at Abbey Road, The original Cuban tile has been preserved throughout the house, wherever possible. Upon entering the spacious living room, a large tropical sectional queen sleeper sofa allows you to comfortably watch the 46” flat screen TV/DVD. Also available is an I-Pod... View all property information
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5 of 5 stars Reviewed 7 December 2014
My spouse brought me to KW to celebrate my birthday, what a truly wonderful time we experienced on our entire trip. Lennon Lodge was absolutely cozy, comfortable, and private...
5 of 5 stars Reviewed 31 October 2014
We stayed in Lennon's Lodge for 7 days, and wish we could have stayed forever. The property itself is clean, quiet and private and the Lodge itself is beautiful, well-kept and...
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Private Outdoor...
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
  • ?
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About this property
Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom... View all property information
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5 of 5 stars Reviewed 24 February 2015
We could not have found a more perfect place to rent for our Girls Weekend- My girlfriends and I enjoyed this house so much! The rooms were big and spacious, the balconies...
5 of 5 stars Reviewed 11 March 2013
2br 2 bath with sleeper sofa in main room. Pictures are accurate. Private pool and location make this an ideal stay for more than 3 nights. VERY close to the action on Duvall...
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Suitable for children
  • x
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  • Elder access
  • ?
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About this property
Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been... View all property information
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5 of 5 stars Reviewed 30 July 2014
This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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Studio, 1 Bathroom, Sleeps 2
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  • Suitable for children
  • x
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  • Elder access
  • ?
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About this property
This wonderful unit is set apart from the others with cathedral ceilings and a skylight in each room; light and airy and yet very cozy and comfortable. This efficiency condo is perfect for 2 and can even accommodate the occasional guest with the living room sleeper sofa. The bedroom has a... View all property information
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3 of 5 stars Reviewed 8 October 2014
The place was pretty decent overall however it is not in the safest feeling part of town. We learned that it is right next to public housing and there are some loud neighbors at...
2 of 5 stars Reviewed 21 August 2014
The property was cute, but the surrounding areas are quite scary. The pool is a few blocks away... No Wi-Fi. The location is quite convenient and the suite was rather clean...
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  • x
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  • Elder access
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About this property
Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
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5 of 5 stars Reviewed 28 January 2015
Loved our stay at toon hall. Awesome home away from home. Had all amenities we needed and location was great. Property was private and secure. Staff was responsive to...
5 of 5 stars Reviewed 2 July 2014
We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable...
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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  • Air Conditioning
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  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living... View all property information
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3 of 5 stars Reviewed 27 December 2014
The location is perfect--a block off Duval and 4 blocks from a grocery store. The two connected houses are somewhat run down but adequate and probably typical for "Old Town" Key...
5 of 5 stars Reviewed 5 December 2014
Poolside Paradise was the perfect place to call home during our stay in Key West and completely met our expectations. The two homes and pool were beautifully kept and staged for...
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About this property
Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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5 of 5 stars Reviewed 30 October 2014
We have stayed in this lodging five times. It is very clean and service is excellent and friendly. The location is secluded and especially quiet.
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Suitable for children
  • x
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  • Elder access
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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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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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2 Bedrooms, 2 Bathrooms, Sleeps 4
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About this property
KEY LIME PIE - A little slice of Paradise located only one block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Key Lime Pie is located on a small narrow lane that is a secret from even many of the locals in Key West. This house has been lovingly... View all property information
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5 of 5 stars Reviewed 5 December 2012
Our stay was for a month and the property was great and the location was awesome We walked to everything we need and was on a nice quite street(lane) Great neighbors
3 of 5 stars Reviewed 26 April 2012
We returned here to stay for 6 weeks and we like the location. Thankfully, the bed mattress has been replaced and there have been a few other updates and new wifi which we really...
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  • Suitable for children
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About this property
Inside, you will find all of the comforts of home and This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor.... View all property information
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4 of 5 stars Reviewed 12 February 2015
Family House is in a great location -we could walk everywhere we wanted to go in Key West. We were on vacation with 6 adults. The major downside to this house is that the sofa bed...
5 of 5 stars Reviewed 28 January 2015
The best. The family members stated it was the best ever. Duval offered the best food and drink. Historical amenities offered an educational amenity to offset the drinking...
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Suitable for children
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About this property
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached... View all property information
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5 of 5 stars Reviewed 26 October 2014
This property has everything you will need when away. So many little touches it makes you feel like you are at home. We rented with two other couples so 6 adults total and never...
5 of 5 stars Reviewed 3 August 2013
My husband and young son (8) and I stayed at Villa Paradiso for one week in July and had such a fabulous time. Coming from a fortnight of racing around the parks in Orlando, Key...
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  • Air Conditioning
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  • Safe
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  • Smoking allowed
  • Suitable for children
  • x
  • x
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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 29 January 2015
Loved the boat and amenities. We took kayaks out for sunset pictures. private and quiet yet close to Key West.
5 of 5 stars Reviewed 23 January 2015
The boat is perfect for a couple that wants to get away. The boat was very clean and the marina has nice amenities. James was a wonderful host telling us everything we needed to...
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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  • 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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  • Suitable for children
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About this property
CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large living room and dining room with a kitchen that overlooks your own patio. Lush... 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.