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Key West Cheap Vacation Rental Deals

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    Travellers to Key West are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    79 Matching Rentals in Key WestView all 319 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Seaside Condo 2 pools summer specials1 / 17
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As I stand on the front porch of this little Hidden Story-Book Cottage in the Old Town Key West, I could swear I’m in a neighborhood in the Bahamas on Green Turtle Cay. In case you didn’t know, Key West and Green Turtle are ‘sister islands,’ and this quaint neighborhood in the middle of the island,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Butterfly Garden ~ Monthly Rental1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
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    Reviewed March 31, 2015
    I have stayed at the Butterfly Garden more than once while in Key West on business. I enjoy the location as everything is a short bike ride away. The landscaping is amazing, the...
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    About this property
    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 16
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 2018
    I booked this property for a 28 day stay and I'm so glad I did! What a great location! An easy 4 minute walk to Duval St and a 3 minute walk to the spectacular MLK Community...
    Reviewed August 5, 2018
    one of the best places and time i have in Key West.Super house,total privacy,very quiet naibourghood.coming back next year
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    737 The Place, a  Monthly Rental Old Town Key West1 / 15
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 2015
    Located in the historic Old Town section of Key West, this is one of three units in one building. The owner lives in the front and their friend in the middle unit, both were...
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    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven....
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Osprey1 / 48
    (45)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 24, 2016
    We stayed at the osprey in bungalow #8. This place was clean with a very comfortable bed, sitting area, kitchenette with a full size refrigerator and a nice deck for morning...
    Reviewed March 21, 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
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    About this property
    Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West has to offer! This bright and colorful studio Key West rental cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    When I went to preview this townhome called Cabana Boheme, I was intrigued by the name. And so it was fitting to its nom de plume, that I drive the 10 blocks in our hand-painted conch cruiser truck, transformed into rolling art by local mural artist Rick Worth. Key West is like that, as much a...
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    Key West, Florida Keys 33040
    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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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Internet Access
    • Sauna
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through breeze and expansive views of the tropical courtyard. As assigned private parking space will convey with your rental. You can feel secure in our fortress or a property. Key West is...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spectacular Atlantic Ocean View Condo (MONTHLY)1 / 26
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Hot Tub
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2016
    When we arrived at the condo there was construction going on around it and it was a little confusing. However, when we got in the room it was breath taking !! The view is...
    Reviewed December 27, 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
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    About this property
    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 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
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    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 21, 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise Place1 / 24
    (29)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 3, 2018
    This one bedroom 'cottage' was located in beautiful Key West and provided easy access to major hot spots. The accommodations were comfortable and clean, including a washer and...
    Reviewed July 8, 2015
    We stayed at Paradise Place for 6 days and totally enjoyed it. Very clean and plenty of towels, beach towels an other extras. The spa pool was awesome with beautiful palm trees...
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    About this property
    Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach A ground level one bedroom one bath Key West Old Town condo located in the Palm Gardens community in the heart of the Art District and just six blocks from Duval...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Key West Charming1 / 23
    (26)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 7, 2016
    The location was awesome, close to everything. We loved that it was close to Blue Heaven. The condo was too small for our liking, but that's not to say that it isn't...
    Reviewed December 2, 2013
    this was a great condo and the location was perfect for the boat races. very clean and everything was just as stated.no problems at all!! and @home in key west were great...
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    About this property
    Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental! Located at the Shipyard Condominiums condo rental in Key West. This downstairs 2 bedroom 1...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends Nestled in a quiet corner of the Shipyard Condominiums in Truman...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    • Waterfront
    • Sauna
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Come enjoy some of the great back country fishing the Lower Keys has to offer! Welcome to Bonefish Lodge, an upscale, tastefully furnished, 2 bedroom, 2 bathroom duplex on Big Coppitt Key. This home is located on a deep canal just minutes from Snipe Point and the gulf, or out front to the Atlantic...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Celebration1 / 22
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Beautiful, recently updated 2 bedroom apartment located in a popular community of Truman Annex, only a short bike ride to Fort Zachary Taylor Beach 2 bedroom 1 bath Shipyard condo located in Truman Annex. New floors, fresh paint, all new furnishings, artwork, linens and towels. Be one of the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    City Cay1 / 22
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
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    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2017
    We stayed for a week at City Cay. The location could not have been any better. The condo was supper clean and well maintained. We would definitely stay here again! It is a one...
    Reviewed August 1, 2016
    We loved City Cay. It was a small condo with one king bed, a futon and a small kitchen, but it was exactly what we needed. The bed was super comfortable. The bathroom was...
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    About this property
    Recently renovated, modern and cozy upstairs apartment with a large balcony overlooking the neighborhood Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This lovely Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 23, 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    Reviewed July 2, 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised...
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    On Hemingway's Rounds ~ Monthly Rental1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2016
    Very comfortable home, well furnished, very homey. Great location. Management company very responsive to all questions and needs. We loved our stay at On Hemingway's Rounds.
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    About this property
    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ibis1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 10, 2011
    My location was so convenient that I could walk everywhere and I did. I loved the fact that it was so quiet at night. When I needed service on the microwave, it was provided...
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    About this property
    Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    NEWTON'S NEST (Monthly Rental) Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls,...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Coral Garden1 / 23
    (28)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Grill
    • DVD Player
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    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 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 August 16, 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
    For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer! 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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps away from the large lagoon style pool surrounded w/lush tropical landscape. 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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off. Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wind Swept1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2013
    The house was great Loved being on the golf course very quite area great pool Security was very nice and helpful The staff: At home was great Libby is the best
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    About this property
    Screened porches up and down for you to enjoy the the extra living space in this lovely townhome. Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. This lovely 2 bedroom 1.5 bath...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Grill
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect view from your screened porch to watch golfers play the first hole on the Rees Jones designed Key West Golf Course. 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...
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    Location Information
    Key West, Florida Keys 33040
    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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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes. Welcome to your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lavender Jungle1 / 24
    (27)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2018
    My husband and I stayed here last week and was very pleased! We would definitely stay here again in the future and we would recommend this place to anyone. Great location...
    Reviewed June 11, 2018
    Perfect spot. Literally walking distance to the beach to the water park to Duval street to everything . The front had a porch and the back had a deck with a grill and table. Two...
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    About this property
    This gorgeous apartment is located in one of Key West's most attractive, quiet, and convenient neighborhoods, Truman Annex, close to many attractions and also Fort Zachary Taylor Beach Beautiful 2 bedroom 1 bath downstairs Shipyard condo for rent Key West located in Truman Annex, this home has...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Emma's Escape1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2013
    We have been staying at 717a Emma for four years now. We started for one month and next year, we'll be there for three. I think that this property has one of the most amazing...
    Reviewed February 6, 2013
    Once again we enjoyed our winter stay in Key West. The climate in the main attraction, but Key Westalso full of interesting people and places. The condo became a home away...
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    About this property
    Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street. Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Emma's Secret1 / 22
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens. Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a large...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space. You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, just a few steps from the pool and you've reached your...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Bay1 / 25
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Terrace
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2015
    At Home in Key West was nice to work with. We arranged everything via email. We reserved a smaller cottage, but when that was no longer available, At Home upgraded us to Siesta...
    Reviewed March 19, 2015
    This condo was fine. Nothing great but the location is terrific as it sits two short blocks off of Duval St. pretty much centrally located between the ends of the island. And...
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    About this property
    Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex! Beautiful two bedroom one bath upstairs Key West condo rental in Truman Annex, just steps away from the shared pool and within walking distance of anything you'd want to do in Key...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Waterfront
    • Sauna
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Deluxe One Bedroom Condo1 / 18
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Air Conditioning
    • Shared Garden
    • Wi-Fi
    • Washer
    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 24, 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which...
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    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tranquility1 / 24
    (29)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Balcony
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed June 28, 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked...
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    Location Information
    Key West, Florida Keys 33045
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 24
    (31)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
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    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2018
    Totally will do this again great place to thanks Bonnie for allowing us to be able to rent the room will recommend it to all of our friends and family
    Reviewed August 5, 2018
    Yes it’s close to the airport but the planes land and take off when you are awake. Location allowed me to breakfast on Stock Island while being close enough, but not to close...
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Sunny View1 / 24
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 5, 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 February 9, 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
    Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street. 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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Private Garden
    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Strikingly set in the oft-missed Key West mid-town neighborhood, we find Island Elegance, making a classical curbside statement with its craftsman-colonial architecture, lush mature tropical landscaping, and white picket fencing. Built in 2005, the design of this home incorporates the timeless...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Brisa Del Mar1 / 24
    (13)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 18, 2015
    This condo was just what we wanted. It had everything we needed including beautiful views. The condo was clean and the beds comfortable. The pool was great and the hot tub was...
    Reviewed January 8, 2014
    The condo at Barisa was perfect, lots of space and breath taking views every day. Everything you could possibly need was right there. Not far from old town and all the beaches...
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    About this property
    Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental! This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean. Enjoy spectacular views from this waterfront rental condo in Key West of the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Finn Key1 / 24
    (33)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 6, 2018
    I traveled with my best friend and her husband to Key West, and we decided on renting Finn Key for about a week. The location was phenomenal - we barely needed the car! We could...
    Reviewed February 10, 2016
    Lovely condo,great location, have stayed at Truman many times. Condo is clean and comfortable, neighbors upstairs must live here full time, they walk a little heavy but I...
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    About this property
    Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat! A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West! “Bayview Harbor” is a beautiful, peaceful retreat ideally located on Southard Street, walking distance to the beach at Fort Zachary Taylor Historic...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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