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Key West House Rentals

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    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group had...
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    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is cozy and comfortable. Loft with Queen Bed overlooking the living room. Cathedral ceiling and Hardwood floors. This place has everything you need to live comfortably while steps from... View all property information
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    Key West, Florida Keys
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main... View all property information
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    Key West, Florida Keys
    1 / 24
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 30 July 2015
    I stayed on Shark Key with my Mum, aged 82, husband and niece. We had an enjoyable stay using both the pool area, the lagoon and the kayaks. Firstly the house, the kitchen...
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    1 / 22
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    CORAL GARDEN: 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock. Fully-equipped kitchen, comfortable dining area, and living room sports a gigantic 52' HDTV for your viewing pleasure. Master bedroom with bath ensuite offers a comfy queen bed; 2nd bedroom with bath ensuite... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 12 September 2013
    Our visit to Key West was amazing. At Home in Key West Inc. has the best services they were very informal and personal. At Home made sure we had everything that was needed for our...
    5 of 5 stars Reviewed 16 August 2013
    We were thrilled to see that the home was so well kept and looked exactly like the photographs. I would definitely recommend people staying here especially if you have children...
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with... View all property information
    Location Information
    Key West, Florida Keys
    1 / 32
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Patio
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    About this property
    Oceanview Secluded Private Two Acre Estate” A PRIVATE TROPICAL PARADISE ON THE ATLANTIC OCEAN. WHITE IBIS INN - LOCATED IN SUMMERLAND KEY ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special discounted price from our White Ibis Inn. If you are... View all property information
    Location Information
    Key West, Florida Keys
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    1 / 27
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    LINGER LONGER: 2 bedroom 1.5 bath townhome in Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on the 2nd floor. Downstairs is an open floor plan with kitchen/dining/living room and half bath. French doors... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    4 of 5 stars Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived at...
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    1 / 26
    5 of 5 stars (33) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 11 July 2016
    This rental was exactly as described. The home was clean and well cared for and the owners, Jim and JoAnne were a pleasure to work with from start to finish. The transaction was...
    5 of 5 stars Reviewed 7 July 2016
    We just returned from a 10 day stay at Casa Del Sol, in the Truman Annex section of Key West. The two bedroom, 2 l/2 bath townhouse had everything we needed to make our stay...
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    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    * This vacation home is available to rent on a monthly basis only * Dating all the way back to 1884, this delightful 3BR home is located in Bahama Village, part of Key West's prominent Old Town neighborhood. This single-family home is available to rent on a monthly basis. If you'd like more... View all property information
    Location Information
    Key West, Florida Keys
    1 / 24
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Terrace
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    About this property
    Great for large groups - 6 bdrms, 3 bathrms, sleeps up to 14 adults, White Ibis Inn just 15/20 minutes drive from Key West. Sometimes we run a special discounted price from our White Ibis Inn. If you are interested to book our place, please let us know how many people in your group, any pets,... View all property information
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    Key West, Florida Keys
    1 / 38
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    About this property
    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half... View all property information
    Location Information
    Key West, Florida Keys
    1 / 12
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... View all property information
    Location Information
    Key West, Florida Keys
    1 / 31
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    KEY WEST CASA: One of only a few 3 bedroom 2 bath condos in the Shipyard complex in Truman Annex. Enter the fully stocked kitchen to the living room to the French doors that open onto the back porch. The downstairs bedroom is just to your left and offers 2 twin beds next to the bathroom. Upstairs... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 12 June 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
    4 of 5 stars Reviewed 9 April 2014
    Check-in & out was excellent, no problem, Great! It was so nice to feel like you were home and not stuffed in a little one room. The location is perfect, you are close to...
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    1 / 22
    4.5 of 5 stars (84) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    BAHAMA DREAMING: One Of At Home In Key West's Most Popular Rentals! Bahama Dreaming is a traditional 3-bedroom Conch cottage located just steps from Duval Street. With it's fantastic location and amenities this home offers it all. The main level has 2 bedrooms, one containing a comfy queen size... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 4 August 2016
    My husband and I and his family stayed here July-August 2016. The house was clean and just perfect for us. The location was superb as Duval was steps away. It was a great location...
    4 of 5 stars Reviewed 21 June 2016
    We have just returned from our yearly girls trip to Key West. We are a group of 6 women in our late 50's (60's) who visit every year in June for a week of fun. First, let ,e...
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
    Location Information
    Key West, Florida Keys
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    This is an amazing summer rental. Available during June and part of July only for either long weekends or by the week. Stunning location within the old town of Key West, over two levels, full kitchen, bbq, 2 bedrooms, shared pool. (Only between 4 houses) It just doesn't get better than this This... View all property information
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    Key West, Florida Keys
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    1 / 27
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 13 April 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
    5 of 5 stars Reviewed 3 April 2015
    We had an incredible time at the Bahama House in Key West. We were in town for my sister's wedding and our party included my parents, my wife and two young children and my sister...
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. 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... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 8 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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    1 / 28
    5 of 5 stars (3) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off-street. Built for entertaining from the wide open floor plan that encompasses the spacious living room and grand kitchen to the magnificent pool. Master bedroom with bath ensuite shares first floor with... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 6 May 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard, spacious...
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A spacious 3 bedroom townhome... View all property information
    Location Information
    Key West, Florida Keys
    1 / 12
    3.5 of 5 stars (3) Average
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 10 February 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
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    1 / 25
    4.5 of 5 stars (54) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    AMELIA HOME - 2 bedroom 2.5 bath home with sparkling private pool only four blocks from the Atlantic Ocean and one block from Duval Street entertainment. Kitchen complete with everything to create a gourmet meal. Large open dining and living area. Lush garden with private pool that gives one a... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 12 April 2015
    What a great place to stay. Location is perfect. Everything you need is supplied. Decor and Landscaping were also wonderful. Already talking about next years stay. Nothing...
    5 of 5 stars Reviewed 2 April 2014
    Amelia Home was a great place to stay and experience Key West. The house is very clean and in excellent condition. The pool made the stay.The location is great. You can walk to...
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    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Just one-half block from famous Duval Street, this turn of the century cigar makers cottage lies in the center of Old Town. Just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This KEY WEST HOUSE is just steps from restaurants, night life,... View all property information
    Location Information
    Key West, Florida Keys
    1 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors that... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 29 January 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    1 / 21
    4.5 of 5 stars (35) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen TVs, stereo,... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 23 January 2014
    We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.
    5 of 5 stars Reviewed 20 November 2013
    We just love this little get away home that we get to stay at when in Key West. The new owners have done a nice job of re-modeling and the Leeward Isle is so comfortable.
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    1 / 23
    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ISLAND WIND: When balmy breezes beckon and tropical retreats call your name, Island Wind will be just the escape you need. Located in the pristine gated community of Windward Park this 2 bedroom, 2 bath Bahamian-style townhome is surrounded by lush landscaping and views of a sparkling swimming... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 26 May 2016
    Spent a a week here. We loved everything about it. Great neighbors and relaxed atmosphere. House was absolutely perfect. Everything you need is there, just bring a bathing suit...
    4 of 5 stars Reviewed 5 December 2013
    Enjoyed Thanksgiving week here. Island Wind is in a perfect location. It is an easy walk to the southern most beach & a doable walk to Mallory Square. Duval is only a block...
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    1 / 18
    4.5 of 5 stars (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. One block from Duval Street , it is close to restaurants, shops, galleries and clubs. The Atlantic Ocean is only 4 blocks away. The... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 21 July 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
    4 of 5 stars Reviewed 19 March 2014
    We loved Tropical Dreaming! The location is excellent, just two blocks from Duval and a few blocks from South Beach and practically in walking distance to everything. The home is...
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    1 / 24
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Internet Access
    • Satellite TV
    • Balcony
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    A PLACE IN PARADISE - Experience Key West living in this 2 bedroom 2.5 bath Conch-Style home in Truman Annex. This home features a fully equipped kitchen, dining area, half bath and living room with french doors that open to a sunny private patio. Outside dining area ideal for Happy Hour, grilling... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 13 November 2013
    I've been going to KW every year for about a decade and have learned that your home base for the week can be the difference between a good trip and a truly great trip. I've stayed...
    3 of 5 stars Reviewed 18 July 2013
    We have a family of 5 (including three boys: 19, 17 and 11). The location was great. We had a car, but really never used it. Instead, we rented bikes and used them a lot. The...
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    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar... View all property information
    Location Information
    Key West, Florida Keys
    1 / 29
    4.5 of 5 stars (11) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • DVD Player
    • Terrace
    • Parking
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport. Fully equipped kitchen, HDTVs, WIFI and off-street parking for... View all property information
    Location Information
    Key West, Florida Keys
    3 of 5 stars Reviewed 10 April 2014
    Rent this condo if you are looking for a place out of the fray but nonetheless close. It is 10 - 15 minutes to Duval Street, and very bikeable. Stock Island eateries (Roostica...
    4 of 5 stars Reviewed 10 October 2013
    A group of 7 of us stayed here for 4 days and it was a very nice time. There was a slight shortage of towels but there was a washer and dryer that was fast and easy to use in the...
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    1 / 27
    4.5 of 5 stars (15) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Balcony
    • Terrace
    • Private Outdoor...
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    ALLURING PORCHES – This 2 bedroom 3 bath townhome with den in Truman Annex is the tranquil escape you’ve been looking for. 50% larger than similar homes in the area. First level is the kitchen with all you need, dining room, oversized living room with high-end electronics, den that doubles as... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 1 November 2015
    Everything as advertised and more. Immaculate, tastefully decorated, roomy. Close to Duval. Porches on each bedroom and off living room. Huge master bedroom with large porch...
    5 of 5 stars Reviewed 9 August 2015
    I was a little apprehensive about booking this place because it didn't have many recent reviews, but I am very glad we booked. The price was very reasonable for Truman Annex and...
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    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman... View all property information
    Location Information
    Key West, Florida Keys
    1 / 19
    4.5 of 5 stars (36) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Internet Access
    • DVD Player
    • Terrace
    • Satellite TV
    • Balcony
    • Private Outdoor...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with laundry closet. Guest bedroom on the main level with 2 twin beds... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 17 January 2016
    This place is very nice and has all the convenience's of home. Located one block off of Duval street so you can walk Duval, drink and not have to drive home. The weather was...
    5 of 5 stars Reviewed 14 May 2015
    Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.
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    1 / 27
    4 of 5 stars (13) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Private Outdoor...
    • Internet Access
    • Terrace
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    CORAL SUITE: 2 bedroom 3 bath townhome for 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master bedroom has a private balcony. Guest bedroom is roomy and private. The Murphy bed in the living room is sturdy and comfortable. Kitchen is equipped with all... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 10 May 2014
    There were 4 in our group (family), and we had a lovely time! It was a bit difficult to find, especially for the pizza delivery man...lol Despite Tropical Storm Issac, we had a...
    5 of 5 stars Reviewed 17 April 2014
    I am a seasoned visitor to Key West. Over thirty visits thus far. This was the best way to spend a week on the island. Everything was superb. Nothing was out of place...
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    1 / 25
    4 of 5 stars (34) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Terrace
    • Parking
    • Internet Access
    • Satellite TV
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    CROWNER'S JEWEL: Delightful 2 bedroom 2.5 bath Conch-style townhome in the quiet gated community of Truman Annex, surrounded by historic buildings and tropical flora; only a short walk to Duval Street. Master bedroom has small bath ensuite and private balcony (note: both bathrooms have shower... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 5 November 2014
    Great Place! 2 blocks from Duval. Spacious, great amenities. Showers are tiny but at least there are 2 which helps bigger groups get ready. Clean. Nice neighborhood.
    4 of 5 stars Reviewed 17 April 2014
    Excellent rental company with at Home In Key West!!! We can't wait for our next trip to Key West... We will definitely be using at Home... And we will always stay in Truman annex!
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    1 / 17
    5 of 5 stars (22) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Patio
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Forget that "been there, done that" hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and "Sunset Celebration". The original local artwork throughout... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 13 September 2015
    I arrived on a rainy, nasty day in Key West. It was pouring. Duval Street was flooding. The temperature was in the 50s. But I was in Key West, so it couldn't be all bad. It...
    5 of 5 stars Reviewed 10 December 2013
    We have been traveling to Key West 1-2 times a year for about 15 years and have stayed everywhere from the most economical to the high end resorts and will confidently say this...
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    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
    Location Information
    Key West, Florida Keys
    1 / 28
    4.5 of 5 stars (24) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    DUVAL PENTHOUSE: Fabulous location, beautiful furnishings and plenty of space, suited to the casual lifestyle here in Key West. 2nd and 3rd story of the building; 3 bedrooms 2.5 bathrooms and an open floor plan. Living room, kitchen and master suite on the 2nd floor; French doors open from living... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 18 February 2015
    Love the Duval Penthouse; our second year staying there. Fantastic location, clean, well taken care of. Only one thing I would change... the mattress in the Master bedroom is...
    4 of 5 stars Reviewed 26 March 2014
    The place was awesome. As everyone says, the back bedroom is a bit noisy being right on Duval and next to Willie T's but still a great place. I found that leaving doors open for...
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    1 / 22
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 28 July 2016
    We had a great stay with Andrews Inn. We stayed in the Mango Hideaway.. Very quant and cozy cottage feel and super clean. The bed was so comfortable I felt like I was home...
    5 of 5 stars Reviewed 16 July 2016
    Key West is my favorite vacation spot and Andrews Inn has never disappointed me. Everything was top notch, from the suite to the pool, the recommendations to the scrumptious...
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    1 / 25
    4.5 of 5 stars (24) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Plan your Fall getaway! Visit now through OCTOBER 22nd 2016 and get a 15% DISCOUNT. Please see our Specials page for all terms and conditions. Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 18 April 2016
    Love this location. Very convenient to Ft Zachary Beach ..., Mallory Square . Can easily walk to anywhere from condo . Duval St , two short blocks away . Have stayed in Truman...
    5 of 5 stars Reviewed 27 March 2016
    I stayed with a friend at Historic Hideaways,"Foundry" rental property in june of 2014. I have been to Key west many times. I have stayed in many Hotels and B&,Bs. I truely...
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    1 / 20
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room. Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014. There is a community pool area to... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 5 July 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
    4 of 5 stars Reviewed 5 December 2013
    Very nice 2 bedroom 2 1/2 baths located in an excellent location. Walk right down to Duvall Street. Located at the quite end of Duvall. Great accomdations but a bit pricey.
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    1 / 26
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Grill
    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Satellite TV
    • Terrace
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a prestigious gated community in Old Town. Surrounded by tropical greenery in a beautiful quiet gated community 2 blocks from Duval Street and Mallory... View all property information
    Location Information
    Key West, Florida Keys
    1 / 16
    4.5 of 5 stars (38) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 17 October 2012
    This amazing little house had everything you could need to make a Key West vacation even better. The whole house was clean, and with a tropical flair that told you the moment you...
    5 of 5 stars Reviewed 1 September 2012
    The house was spotless. Easy to live in. Close to everything. Comfortable. The small pool/grotto is where I hang out in my memories. Everyone was sweet, accommodating and...
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    1 / 34
    4.5 of 5 stars (15) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Grill
    • Satellite TV
    • Patio
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways and wander by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 2 August 2013
    After reading great reviews about the Villa Tropicale, we rented this property for six nights last month. We were traveling with a group of eight and wanted a large home where we...
    5 of 5 stars Reviewed 27 January 2013
    This was not our first stay at Villa Tropicale and we certainly intend to come back. When we first opened the gate of the property a few years ago, we were delighted to discover...
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    1 / 9
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Why stay in a cramped hotel when you can relax in a private, quiet, and peaceful 2-acre estate! We are now running an special discounted offer for the Fall of 2016 WHITE IBIS INN - LOCATED ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special... View all property information
    Location Information
    Key West, Florida Keys
    1 / 34
    4.5 of 5 stars (31) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Private Outdoor...
    • Balcony
    • Parking
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Truman Annex. Decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. First floor features open living/dining area, kitchen and half bath. Kitchen is well... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 5 April 2015
    The Foundry in Truman annex is where I stay every time I vacation in KW- close to everything but quiet & peaceful for relaxation.
    4 of 5 stars Reviewed 22 January 2014
    We stayed in a condo in the Truman annex Foundry this vacation, and we really loved the location. We could walk easily to the Key West Bight, the Mallory Square area, the...
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