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Villas in Key West, FL

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From
£111
Per Night
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1 / 21
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1 Bedroom, 4 Bathrooms, Sleeps 2
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£315
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1 / 25
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3 Bedrooms, 4 Bathrooms, Sleeps 6
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£132
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1 / 26
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Studio, 1 Bathroom, Sleeps 2
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£159
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1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
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 31 December 2013
Really enjoyed staying at Shelleys Rooftop. Far enough down Duval St. to be away from the crowds but just a walk away to the crowds and popular bars. Spent Christmas with...
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From
£120
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1 / 13
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Housekeeping...
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share... View all property information
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4 of 5 stars Reviewed 10 July 2014
Nice little cottage with private patio, located adjacent to the pool. Cottage was clean and well maintained, and had a full kitchen with all the amenities. It was walking...
5 of 5 stars Reviewed 22 December 2012
Kevin, Shelby, and all the folks at KW Hideaways, I wanted to take a moment to thank you all for a wonderful experience! You and your team worked hard to ensure everything...
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1 / 8
1 Bedroom, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • City/Skyline Views
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
MONTHLY RENTAL ONLY Fantastic 2nd floor studio with a large private deck located just one block from famous duval street. This tree top studio is cozy. For your convenience there is a kitchennette with a 2 burner stove, microwave oven and a toaster oven. There is a brand new queen size sleeper sofa... View all property information
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£88
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1 / 27
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before... View all property information
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5 of 5 stars Reviewed 5 August 2014
The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or a...
4 of 5 stars Reviewed 25 July 2014
The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we were...
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£184
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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
  • Dryer
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Wake up to the sun rising over the sparkling Atlantic Ocean. Watch heron fish for breakfast in the flats below as you drink your coffee. Stretch out on the balcony while flocks of pelicans soar above you and the rocks disappear and reappear with the tide below you. Sip a cocktail and watch the... View all property information
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5 of 5 stars Reviewed 2 November 2014
This two bedroom condo has everything! Beautiful views, beautiful decor, incredibly clean and comfortable and equipped with everything you could want. We stayed for four days and...
5 of 5 stars Reviewed 23 June 2014
We had a wonderful stay at the Atlantic Sunrise condo. The condo was tastefully decorated and well appointed. It was roomy and very comfortable for the four of us. The fine...
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£3,526
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1 / 9
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Housekeeping...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
If you have ever had the fortune to wander the historic streets and lanes of Key West's famous seaport neighborhood then you know how time seems to stand still. Yet right in the heart of Key West's bustling seaport this blissfully ideal cottage-style house offers all the amenities one could desire... View all property information
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From
£143
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Make memories the whole family will cherish in this great family friendly condo in Key West. It's close to all the major attractions on the island but far enough away that everyone can get a good night's sleep if they want. Want to go to the beach? The condo is a short drive to Smathers Beach.... 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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From
£189
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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (14) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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5 of 5 stars Reviewed 28 October 2014
Hidden Treasure is just that - a hidden treasure located off of Olivia street in The Colony. Lots of space including storage, a great outdoor area, a quiet secluded area and yet...
4 of 5 stars Reviewed 11 September 2014
Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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From
£143
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1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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3 of 5 stars Reviewed 16 November 2014
This is a nice 2 bed 2 bath condo, clean, comfortable, and nicely decorated. The pool and hot tub in this small resort were very nice. Kitchen was adequate with new pans - I...
5 of 5 stars Reviewed 7 May 2014
The location was great. Very Quiet. Exactly as described. Would definitely stay here again! I was also incredibly grateful the for the quick response times to my emails.
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From
£202
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1 / 28
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
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4 of 5 stars Reviewed 30 September 2014
Only issues was the ants running around the kitchen counters. Parking is only for one car. Location was a plus, Jacuzzi was nice to wind down at nite.
5 of 5 stars Reviewed 24 April 2014
The amelia House was perfect! House was so comfortable. Very clean and well taken care of. The rooms were spacious and roomy. Beds were so comfortable and big. Loved the...
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£113
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1 / 28
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1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (20) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!... View all property information
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5 of 5 stars Reviewed 26 June 2014
Our stay at the Abaco Suite through Key West Vacation Rentals was near perfect. The rental company was very professional and helpful. The check-in and out was seamless. We...
4 of 5 stars Reviewed 7 April 2014
TThis is a lovely 1-bedroom townhome situated in an ideal location among 8-9 units on around a truly beautiful courtyard. First off, you really get the bang from your buck at this...
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From
£227
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1 / 27
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
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 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.
5 of 5 stars Reviewed 25 May 2013
An absolutely fantastic holiday home away from home. The cleanliness of the house is an absolute joy, and there is every household amenity to make your stay comfortable. It is...
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From
£126
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1 / 23
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Studio, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southern Palms Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment... View all property information
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5 of 5 stars Reviewed 12 August 2014
We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait to...
5 of 5 stars Reviewed 29 July 2014
From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport pick-ups...
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£126
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1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Details Reviews (25) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair completes... View all property information
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5 of 5 stars Reviewed 9 October 2014
Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
5 of 5 stars Reviewed 19 August 2014
My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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From
£119
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1 / 25
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Studio, 1 Bathroom, Sleeps 2
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of 4 exclusive units at Abbey Road, The state-of-the-art kitchen includes granite counter tops, a Jenn-Air 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft mood lighting under and above the cabinets. There is also an ice-maker on site for fresh ice to prepare your... View all property information
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4 of 5 stars Reviewed 1 September 2014
We found the room to be charming, and a great location for Duval St roming around. Parking can be an issue, but we were happy with our stay. When in Key West one needs to be out...
5 of 5 stars Reviewed 16 November 2013
This little cottage is adorable. I do not have one complaint! Clean, Updated, We maintained. Perfect, perfect, perfect!
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From
£159
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1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
About this property
The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
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5 of 5 stars Reviewed 22 March 2014
A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
5 of 5 stars Reviewed 23 January 2014
The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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From
£286
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1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
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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5 of 5 stars Reviewed 16 August 2014
I came down with my family and we loved this place. We had a direct view of the water and it was amazing waking up every morning to see that. Very relaxing. Friendly people...
5 of 5 stars Reviewed 29 May 2014
This was our first trip to Key West and everything was great including the condo. Very nice view, great pool, short walk to very nice beach. What more would you want.
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From
£88
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1 / 24
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • 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 Queen... 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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From
£221
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1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
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5 of 5 stars Reviewed 13 October 2014
The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
5 of 5 stars Reviewed 25 July 2014
I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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From
£259
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1 / 30
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
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5 of 5 stars Reviewed 10 November 2014
The Key Escape was everything we wanted and more for a relaxing week in Key West -- 5++ stars!!! It was comfortable, modern, and excellent service!
5 of 5 stars Reviewed 9 October 2014
Excellent property and staff! Great location, great beds!!! Very clean. Would definitely rent again!
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From
£132
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1 / 28
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Sea Breeze features all the amenities of home...and 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 brew...there isn't a better way to start your day in... View all property information
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3 of 5 stars Reviewed 30 September 2014
If you don't mind the Anchors away people hanging out around your bedroom porch all hours of the night, or the people up stairs playing basketball at 430 in the morning, you...
2 of 5 stars Reviewed 19 September 2014
The rental office is well organized and accommodating, and that is the only good thing I can say. The unit itself was clean, though sparsely furnished, especially the bathroom...
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From
£381
Per Night
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1 / 24
3 Bedrooms, 4 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort... View all property information
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5 of 5 stars Reviewed 12 December 2013
This is a beautiful property in an ideal location. We had 6 adults and were very comfortable. Once you opened the door you felt like you were at home. Everything we needed was...
5 of 5 stars Reviewed 18 April 2013
The house is perfect. Three couples shared, plenty of room, privacy when you wanted it, just absolutely perfect. Especially great location, within walking distance of...
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From
£88
Per Night
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1 / 25
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Studio, 1 Bathroom, Sleeps 4
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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 29 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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From
£259
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1 / 33
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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 29 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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From
£113
Per Night
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1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The... View all property information
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5 of 5 stars Reviewed 15 November 2014
I booked our condo through VRBO based on location and price. What a great find. Perfect location to Old Town activity and only a mi,e leasurely walk to Mallory Square and the...
4 of 5 stars Reviewed 8 October 2014
Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter! Very...
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£158
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby bars,... View all property information
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5 of 5 stars Reviewed 4 July 2009
My husband and I stayed here with my parents and had a really wonderful time. The house was adorable, clean and had everything we needed. It was close to all the action on Duval...
5 of 5 stars Reviewed 2 July 2009
Great location off the upper section of Duval. Close enough to walk to everything but far enough to be quiet. Perfect size for 2 or 4 people. Clean and comfortable. Would...
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£191
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Grill
  • Internet Access
  • Private Beach
  • Sauna
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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£170
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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 tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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5 of 5 stars Reviewed 21 August 2014
I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
5 of 5 stars Reviewed 18 August 2014
Positioned right with ammeneties, beaches, and bars close by. Short stroll to any need. Place was very clean and with 2 bedrooms, 2.5 baths , pull out beds was very...
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£170
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Inside, you will find all of the comforts of home and more..... 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 22 November 2014
We enjoyed our stay at the Family House in Key West. The house was clean. The beds were comfortable. The house was convenient to most of the sites we visited. The front of...
5 of 5 stars Reviewed 15 October 2014
Stayed here when traveled down fir SOMO Marathon. Beautiful home, had everything we needed. Great location.....able to walk to everything. Parking is a bit tough.......find a good...
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£126
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft... View all property information
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5 of 5 stars Reviewed 2 September 2014
Really enjoyed this place. Pics are accurate as this place looks in great condition. Loved the patio/hot tub area, also the use of the pool just across the street and grill...
5 of 5 stars Reviewed 12 March 2014
We absolutely loved Harrison's Hideaway. It was in the perfect location - 1/2 block off of Duval, a very short bike ride to the beach. It was immaculate, too - must have been...
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From
£119
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
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5 of 5 stars Reviewed 9 August 2014
I stayed at Papa's hideaway for 11 nights. I spent some of the time with girlfriends and the last few days by myself. Torrents of spring was perfect for both parts of my trip...
4 of 5 stars Reviewed 10 February 2014
I stayed in unit number 1 for 7 nights and I didn't want to leave!! The property is safe and secure and is perfectly hidden but still a walk to all you need. There is a bbq on...
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From
£726
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6 Bedrooms, 7 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
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From
£240
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
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5 of 5 stars Reviewed 14 November 2014
Loved this place.It's exactly as pictured online. Loved the heated pool and the tropical feel of the pool area.Great location. Our only complaints: pull out couch needs replacing...
5 of 5 stars Reviewed 20 May 2014
This property is in a fabulous location right in the heart of old Key West and walking distance to everything, we didn't use the car for the six days we were here. Loved the...
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From
£259
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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 full... View all property information
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5 of 5 stars Reviewed 1 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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From
£158
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • 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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£158
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
UPDATE: New King-sized bed w/ pillow top mattress installed June 2015 Outside the front of the complex are the tennis courts. If you choose to stay inside the complex you can enjoy the lush landscape on the inside of the courtyard. Just a short stroll takes you to the relaxing hot tub and then to... View all property information
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4 of 5 stars Reviewed 17 November 2014
The condo was a very nice rental on the south side of Key West. The decor was modern and the condo had a classy feel. The large balcony patio was wonderful to sit out on in the...
5 of 5 stars Reviewed 7 June 2014
This property was a beautiful way to do Key West. Private beach, big salt water pool and Jacuzzi and grills. The view was the best part of the condo! It was also very clean...
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From
£181
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living... View all property information
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£113
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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 restoration... View all property information
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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...
5 of 5 stars Reviewed 1 May 2014
My husband and I spent 10 nights at Heron Hideaway in celebration of our 20th anniversary. Every thing that we needed was provided in this very clean and ideally located home...
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£215
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential... View all property information
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5 of 5 stars Reviewed 1 June 2014
Namely, Case Key West, where we stayed with a group of 6. The staff was more than helpful, especially Rick Haskins. My Husband uses a wheelchair and he was so helpful and we were...
4 of 5 stars Reviewed 2 April 2013
Had a great two-night stay with my all-adult family of 5. The condo has three full bedrooms so it was very comfortable for our group. The condo also features 2 completely windowed...
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£100
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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5 of 5 stars Reviewed 16 July 2014
Excellent location just off Duval street but still very quiet and private feeling. The unit was small but had all the amenities we needed. The private hot tub and the pool and...
5 of 5 stars Reviewed 29 May 2014
I had stayed at Little Havana Suite numerous years ago and loved it. I knew I wanted to stay in the property again... I ended up traveling solo as my other half got stuck working...
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From
£405
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5 Bedrooms, 4 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker... View all property information
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5 of 5 stars Reviewed 3 September 2014
I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
5 of 5 stars Reviewed 30 January 2014
This is a great place for large families to stay. Wonderful courtyard with the pool and the hot tub and lots of areas to entertain. Remodeled kitchen has everything you need...
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£191
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • 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 condos have a range of room types to suite your... View all property information
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4 of 5 stars Reviewed 8 July 2014
1960s property but well maintained with a good pool, new gas grills (all the better for cooking your catch) and located right on the marina. Our unit (1040) was on the first floor...
4 of 5 stars Reviewed 9 September 2013
had a great time, I'll be back.
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located at Papa's Hideaway Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling through the palms, blowing each of your cares away... This Deluxe Studio is located on the ground floor and offers a private porch just off of the pool area. The unit... View all property information
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4 of 5 stars Reviewed 4 September 2014
My girlfriend and I spent 5 days at Papa's Hideaway and absolutely loved it. The place was a quiet refuge from the hustle and bustle of Key West. Most of the fun things to do...
5 of 5 stars Reviewed 25 June 2014
Small bathroom but a great property. Pool was nice and privacy of location was excellent. A block an a half from Duvall Street, 3 blocks from Southern Most Point. Would stay...
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£183
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
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3 of 5 stars Reviewed 5 November 2014
The home was perfect, loved the porch. Everything we needed for a great home away from home vacation was supplied. The only draw back was the shared pool with other rental units...
5 of 5 stars Reviewed 8 October 2014
Papa's Hideaway is the PERFECT place for a group vacation. Everyone has their own room with kitchen and bathroom but there is plenty of space for everyone to gather and eat, drink...
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£240
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
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5 of 5 stars Reviewed 9 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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4 Bedrooms, 2 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
  • ?
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About this property
Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your... View all property information
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5 of 5 stars Reviewed 29 July 2014
Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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£184
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1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... 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.