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Key West House Rentals

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    166 Matching Rentals in Key WestView all 338 rentals
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Casa Havana1 / 24
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
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    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    Best part, it is right off of Duval and close to so many things to do. The beach is 5 minute walk and the community pool is an amazing unused gem. Free bus to lower Duval is...
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    About this property
    Check out the new 'Duval Loop' that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurants are all located within a 5...
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    Thank you so much for the wonderful stay in your home Bob. We will defiantly stay here again if there is availability when we come. Everything from towels, beach towels, sand...
    Reviewed 27 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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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...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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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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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (55)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
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    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This is either the second or third time we've stayed here so that should tell you its quality. Beautiful condo with everything you need for a comfortable home away from home...
    Reviewed 26 May 2018
    Joanne and Jim were very nice and helpful! I loved the house and the location is superb! Beautifully furnished and comfortable. My only concern was the lack of hot water in...
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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
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'. This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Private Garden
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    • 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
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Royal Palm1 / 25
    (4)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2018
    This Foundry rental was very clean. The whole place was well maintained. The Foundry is a very spacious and quiet place to stay, close to everything but feels miles away when...
    Reviewed 14 September 2016
    Highly recommend this rental property. Located in a lovely quiet area but 5 minute walk to Duval Street. Fully equipped property could not have asked for anything more. Lovely...
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    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this...
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Newly remodeled family home with a shared swimming pool and fitness center!1 / 32
    (3)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
    • Washer
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    • Terrace
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    So, lets start by saying the place was clean. BUT, the furniture and rugs were so old and stained. The TV downstairs worked one day then not the next. There are areas on the...
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    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CORAL BREEZE (monthly rental): Imagine yourself living with the vibrant golf course greens in your backyard and cool tropical breezes wafting your way. Coral Breeze has that and more. Two bedrooms share the full bath upstairs. Kitchen, dining, half bath and living room space in an open floor...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this your Key West Vacation home! Cozy 2 bedroom, 1 bath home set on the back half of a residential lot with new kitchen, bath, and furniture. Privacy provided by the fenced outdoor area, with a shaded porch and furnished gazebo for relaxing. The location is 5 minutes max to anywhere on the...
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West...
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    Location Information
    33042, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Real World MTV House Key West1 / 247
    (49)Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2017
    This house was really cool rooms were spacious and massive , the master room was so lavish . Jacuzzi in living room was a great feature and the games room . Only downside was it...
    Reviewed 29 March 2017
    What would you expect when you first see this colorful place? Party?Well, you might bring your group here and party all night long. Or you can take them here to have an...
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    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – on a private island surrounded by sparkling turquoise waters and balmy breezes. How...
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    Location Information
    33040, Key West, Florida Keys
    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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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A LITLE SLICE OF PARADISE: Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite restaurants. Spend a month (or two) in A Slice of Paradise and you may never return home from this Key West monthly vacation home...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Wi-Fi
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    Pet friendly
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    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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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 27
    (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
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    A Touch of Bermuda in Key West1 / 19
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
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    • 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
    33040, Key West, Florida Keys
    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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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Vista Estate Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV...
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    Location Information
    33042, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Patio
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    • Grill
    • DVD Player
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Sunny View1 / 24
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2014
    The property was exactly as described and in tiptop shape. Everything was ready for our stay, the house was comfortable and a fair value.Also, the folks from at Home in Key...
    Reviewed 9 February 2011
    We had a wonderful time. The weather was great. The cottage was in the perfect location, very clean and filled with everything we needed. It was better than the condo we had...
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    About this property
    SUNNY VIEW - Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental Key West perfect escape for a couple or singles looking to get away from it all in Paradise… Located in Old Town Key West this one bedroom two bath cottage is a gorgeous spot to rest and recuperate...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Parking
    • Private Outdoor Pool (Heated)
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo. It's not Bermuda or the Bahamas but better, a...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ecco Domani1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    • DVD Player
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    • Balcony
    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
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Patio
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Terrace
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    • Parking
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAYO HUESO SUNSHINE: Awaken your senses with tropical breezes, turquoise waters and Key West Sunshine in this brand new 2-bedroom, den, 3-bath home. A secluded location yet the best of both worlds allows you an easy stroll over to the sandy shores of Smather's Beach or just a few blocks from the...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 21
    (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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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations. Prior to buying the house in the 1930's for $2,500, George and Ethel Bowe-Thomas lived across the street paying $3.00 per month for rent!...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Flagler Station1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FLAGLER STATION (monthly rental): This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and re-furnished. Large spacious living room and dining area allow plenty of space for entertaining with easy access...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Place In Paradise1 / 24
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Balcony
    • Parking
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    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
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Villa1 / 24
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Parking
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    CORAL VILLA -- Located right in the middle of the action, Coral Villa is a beautiful Key West Florida townhome with 3-bedrooms in the gated community of Coral Hammock. Just off U.S. 1, across the street from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas,...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Quilted Giraffe1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies, deck...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Linger Longer1 / 23
    (22)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    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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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Location Information
    33042, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Key West Seashell Cottage-1 block to Duval, spa1 / 16
    (44)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2018
    This little cottage is tucked away about a block and half from Duval Street. It’s right in the heart of old town but you would never know it. Very quiet and very clean plus has...
    Reviewed 28 December 2017
    We have stayed at other VRBO's and hotels in Key West before, but Seashell Cottage is now our go-to place. It has everything we like: It's truly a cottage, not an apartment...
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    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...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Coral Casita1 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Terrace
    • Grill
    • Balcony
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Parking
    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...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Architects Cottage on Quiet Lane in Old Town1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
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    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 32
    (40)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This place has everything you could need and want while you stay in Key West. Conveniently located near restaurants, attractions and things to do. Very happy with Seaside Place!
    Reviewed 24 January 2017
    What a great house for our one-week getaway over the New Year holiday! We had a group of 11 people, and we were all comfortably housed inside the well-appointed home. From the...
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    La Prive1 / 25
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 December 2017
    This is a beautiful two story rental with a lovely deck that surrounds the property and a great pool area in the back. Off street parking but street parking available if needed...
    Reviewed 21 April 2017
    The four of us stayed at the residence for two weeks. We are all 68 plus. We were looking for a relaxing place to stay and found it. It is a ten minute walk from Duval Street...
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    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests to enjoy. It...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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