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Key West House Rentals

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    Travellers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    184 Matching Rentals in Key WestView all 402 rentals
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    KWO - 2 BR/2 Bath, Private Pool, Separate Cottage1 / 23
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Recently spent 10 days at KWO. This property is superb and reflects a pride of ownership. KWO clearly exceeded the already impressive presentation on the website. Paula and...
    Reviewed 15 August 2017
    Great location in Old Town, away from Duval Street, but still within walking distance to great restaurants and Duval if that's your idea of fun. The house has everything you...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Wi-Fi
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    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Linger Longer1 / 24
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.
    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...
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    About this property
    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    Spacious property with two pools, friendly neighbors and charming location just a short walk to all of old town Key West.
    Reviewed 4 May 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated historic house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most prestigious gated community in the heart of historic Old Town. 2 bedrooms, 2.5 baths; each queen-bed room has...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 15
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2014
    My husband & I found the Conch House online. The property manager, Craig, met us upon our arrival and was very friendly. Throughout our trip, he was very helpful and very...
    Reviewed 22 June 2014
    This property is so beautiful and peaceful.!! Perfect location, 2 short blocks from Duval, 1 block from Ft. Zach beaches. We stayed in the Conch House , We could not have been...
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    About this property
    OVERVIEW The Conch 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 five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    ~ POTTER'S COTTAGE ~ Perfect Home w/ Pvt Heated Pool Just 1 Block to Duval!1 / 26
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    The pictures are entirely accurate, this place is adorable and perfect for two couples. The two bathrooms was a deal sealer for us. It's near the main drag and we love, love...
    Reviewed 17 September 2016
    We stayed at the Potter's Cottage and thoroughly enjoyed our experience. The property was in fantastic condition - fully modern with generally high quality finishes. One full...
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    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    President's Walk1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This place was perfect for the three adults and infant. The proximity to the pool, Duval St., and Green Parrot really made this beautiful condo ideal for a long Key West trip...
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    About this property
    PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    A Touch of Bermuda in Key West1 / 38
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    By the time you arrive, you will already feel like you are part of Jack's family. He will literally bend over backward to accommodate you. We have vacationed in Key West for...
    Reviewed 14 July 2017
    I stayed in Jack's condo (a touch of Cuba in Key West) this past week and we enjoyed every aspect of it. The condo is two bedroom one bath and was perfect for my party of three...
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    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Casita1 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    We stayed at Coral Casita for two weeks with our extended family. We were very happy with the rental accommodation from start to finish. The property was very clean and well...
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    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Island Wind1 / 23
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award winning Windward Park, a gated and secure compound consisting of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ~ CHAVEZ HOUSE ~ World Class Luxury w/ Private Heated Pool & Great Location!1 / 128
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2017
    The Chavez House more than met our expectations. The layout was perfect for our needs with a large room downstairs and two rooms upstairs. The Kitchen was stocked with...
    Reviewed 10 April 2017
    This was my families first stay in Key West. The Chavez house was absolutely beautiful. All modern amenities and the location was close to everything! We didn't need our car...
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    About this property
    The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was Built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool and calming color...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (50)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2017
    We have stayed at Casa Del Sol 2 times, and had wonderful stays each time. Jim and Joanne go out of their way to make sure all instructions are clear and that the condo is in...
    Reviewed 13 June 2017
    Casa Del Sol is a wonderful town house - location absolutely central and within bike/walking to Old Town.All amenities are tip top as was the furniture, porch, bikes etc. They...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Artist Garden1 / 24
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2015
    We stayed at the Artist Garden for our triple birthday celebration (3 friends within a week). The house is beautiful. It is located within Truman Annex. And you can seriously...
    Reviewed 10 April 2014
    We enjoyed a 2 week stay in this beautiful house. The location is perfect. We were only a 5 minute walk to Mallory Square and a 10-15 min walk to other favorite restaurants. We...
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    About this property
    ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point. The home is just a few blocks away from the Southernmost Beach, night clubs, and popular areas which makes it a perfect spot to vacation as it is a quick walk to everything Key West has to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a little piece of Key West Paradise? Well, this is it! This stunning cottage is only steps away from the Historic Seaport and Old Town. The home has gorgeous Dade County Pine which flows throughout the house, opening into a spectacular private pool and garden. There are two bedrooms on...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ~ SOUTHARD COMFORT ~ Breathtaking Home w/ Pvt Pool, Parking & Quiet Location1 / 28
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
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    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2017
    This home's Decor and comfort was amazing. Quite neighborhood with many Fun things close by. Our Daughter was married in the Living room in front of the open doors to the pool...
    Reviewed 5 August 2016
    This was the perfect place for my friends and I to spend vacation. House is super clean. Very private. Close enough to walk to duval but far away from the craziness when you go...
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    About this property
    “Southard Comfort” is true Island living in downtown Historic Old Town Key West. Two story, 3 bedroom, 2.5 bath plus outdoor shower Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    LOCATION! Feel like a Local! Spacious Suite steps off Duval St.-Eyebrow Suite1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 22 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
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    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Newton Street Hideaway: A secluded one bedroom1 / 21
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2011
    We have stayed at the Newton Street Hideaway for several years, and, as soon as we open the door, it's just like coming home! It's fun to spot the improvements made by the...
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    About this property
    28 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Easy Livin'1 / 24
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Coral Garden1 / 23
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Grill
    • DVD Player
    • Wi-Fi
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bloom'n Paradise1 / 24
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
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    About this property
    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ecco Domani1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ECCO DOMANI – Ecco Domani means 'Here Tomorrow' which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off street parking and attractive appointments -- a wonderful Key West escape that you will want to come home to year after year. Enter...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bahamian Reed1 / 24
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Balcony
    • Parking
    • Wi-Fi
    • DVD Player
    • Terrace
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    This is a middle townhouse unit in the Truman Annex section of Key West. The photos are a true representation of the unit. One bedroom had a king; another had two twins...
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    BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street shops, galleries, bars and restaurants, and Sunset Celebration. Gourmet kitchen, bright cheery...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Breezy Bungalow1 / 24
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Great location - within walking distance of Duval Street, Mallory Square, Hemmingway House, and many other attractions that we visited. The Truman complex, where it is located...
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    About this property
    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Crowner's Jewel1 / 24
    (35)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2017
    Stayed recently for a week and while the condo was clean and well maintained , and the location was great the showers were just way too small. There are two bathrooms upstairs...
    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.
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    About this property
    CROWNER'S JEWEL: Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart of the exclusive gated community of Truman Annex. New owner has added lots of upgrades to make you feel welcome in his new home...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Casa Havana1 / 24
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Location is the best. Casa Havana is 1/2 block off of Duval and 3 blocks from everything in Key West. Deck is great for drink and a cigar in the afternoon and having it own...
    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...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casa Grande1 / 24
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    ~ BESS TRUMAN SUITE ~ Luxury Apt In Prime Location, Steps to Duval St & Beach1 / 25
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2017
    This condo was beautiful. The couches and bed were very comfortable. The kitchen looked brand new. There are NO supplies so be sure and bring spices, sugar etc if you plan to...
    Reviewed 6 January 2017
    Great place great location. Perfect for 2 maybe 4. Working with historic vacation rentals was nothing but outstanding. I would recommend this to anyone.
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    About this property
    THE BESS TRUMAN SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET -...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    ~ ISLAND DAYS ~ Spacious 'Coral Hammock' Home w/ Beautiful Pool & Pvt Parking1 / 27
    (17)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Washer
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    We originally rented this house for the end of our Ragnar Florida Keys event that was cancelled and it was going to house 10 adults. Everyone bailed after the race was...
    Reviewed 18 September 2016
    This was a vacation getaway for us after our daughter's wedding. We had a great time and the accommodations were awesome!!! Perfectly located close to the action yet relaxing...
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    Beautiful Poolside Townhome - Perfect for family or Travel with Friends! The Best of Everything! 'Island Days' has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping and off street parking steps to your door complete the resort feel all in a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    ~ HARRY TRUMAN SUITE ~ Luxury Suite w/ Pvt Porch, Steps to Duval St & Beach!1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    The Truman house was clean, nicely decorated and close to everything. Wonderful time in Key West!!!!
    Reviewed 6 July 2015
    The condo was absolutely perfect and a prime location. When we entered it was like waking directly into the pictures posted, absolutely perfect. It was conveniently located a...
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    About this property
    THE HARRY SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 20
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    We have stayed here 2 or 3 times. It is small, but there are just 2 of us and our dog. Works for us! Very cute and cozy. Washer & dryer. Compound is quiet and...
    Reviewed 13 August 2016
    The Cigar House has one the best location you can expect in Key West, close to Fort Zachary, Hemingway's House or Duval St. and all its attractions.This lovely house is full of...
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    About this property
    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 environment - (1) queen bed, (1) queen...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Duval Breeze1 / 24
    (56)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
    Reviewed 26 February 2014
    Loved Duval Breeze! The house was bigger than the pictures depicted and it was so comfortable. Having not only towels and linens available but also basics like toilet paper...
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    About this property
    DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community of Duval Square on Duval Street, in the middle of the action. Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval Street...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Beautiful property. This house was stunning, thank you so much for letting us stay there. All amenities were provided. I love all the plants and trees surrounding the pool and...
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    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included.
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Heated Pool on Duval St!1 / 45
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    Recently a group of twelve close friends traveled to Key West for a few days of fun in the sun. Since we live in the Chicago area we wanted a place to stay that could house all...
    Reviewed 20 March 2017
    These two houses are a great place to stay. All new kitchen equipment, nice furnishings, all rooms have their own private bath plus a 1/2 bath on the first floor og the grande...
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    About this property
    Grand Maison and Petite Maison together sleep a total of 12 guests. They boast 6 bedrooms each with its own en suite bathroom. Spacious with plenty of room allowing for large family get-a-ways, reunions, or wedding parties. Great outdoor spaces where friends and family can gather or taking time...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Duval Penthouse1 / 24
    (24)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Quilted Giraffe1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    Charming historic home, comfy beach cottage feel. GREAT LOCATION, beautiful pool area great for dining under the stars or a relaxing day in the sun. If your lucky you might get...
    Reviewed 7 June 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is...
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    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    A Place In Paradise1 / 24
    (23)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2017
    The townhouse is in the perfect location. Close to everything. The community is very clean and quiet and the pool, albeit small, was great and just around the corner...
    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...
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    About this property
    A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surrounded by historic buildings and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Coconut Cabana: A restored Old Town home with charm & tropical ambience1 / 28
    (38)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Amelia Home1 / 24
    (54)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Amelia Home. This is the Key West Florida vacation home rental you have been seeking, tucked away in one of the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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