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Holiday Rentals near Key West Intl Airport

3491 S Roosevelt Blvd, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 99 Rentals in Key West
    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 50
    (83)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tropical Escape1 / 52
    (88)Very good
    0.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 76
    (42)Excellent
    1.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach1 / 19
    (1)Excellent
    3.6 kilometres from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2019
    We had a group of 5 that stayed here for five days. We had an absolute blast. The property is very clean with modern updates and easily accessible from the parking lot or from...
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    About this property
    This is a truly rare find! And we know as we have been searching high and low for 5 years across Key West until we were ready to commit to this absolutely stunning property! This is a privately owned townhouse within the exclusive resort of Santa Maria Suites. Not only is it rare to find a...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Top floor, two bedroom,two bath condo with private balcony,close to the Ocean1 / 47
    (4)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2018
    This is the second time we have stayed at this property, the first being in 2016. It still is a conveniently located, quiet and peaceful condo with reserved parking. It is...
    Reviewed 25 January 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
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    About this property
    This 2 bedroom, 2 full baths, unit with kitchen, offers all the convenience and comfort of your own home. It is spacious and fully equipped. Private, password protected U-verse wi-fi. This two bedroom, two full baths condo with kitchen and private balcony, offers all the conveniences of your own...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Isle Of View II1 / 48
    (4)Excellent
    2.3 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Secure Parking
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2020
    We had a wonderful stay. The boat was clean, the captain was awesome and his first mate absolutely adorable. The sailboat is docked at a beautiful marina with lovely pools...
    Reviewed 22 January 2020
    This trip was amazing! My family of 5 stayed on the sailboat for 6 days. We took two day sails and Captain Jeff was awesome. We had lunch on one of the Key islands and we...
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    About this property
    Luxurious and spacious accommodations aboard this elegantly designed 45' Morgan Nelson Marek sailing vessel. Moored on first class dock space in front of the newly constructed Key West Perry Hotel, your stay will begin with welcome and cocktails as you board. Once you've settled, make your way to...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Studio Blu1 / 15
    (1)Excellent
    3.0 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    We stayed at Blue on White Jan-Mar of 2017 and couldn't have been happier with our choice! The apartment is cozy (it is a studio) but at the same time is well maintained and...
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    About this property
    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this nightly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided! This property will meet all of the demands a...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Oceanfront 2 Bedroom 2 Bath Condo Key West Florida1 / 17
    (14)Excellent
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Waterfront
    • Sauna
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2019
    This was a nice two bedroom condo directly accessible to the elevator and you park under the unit. It is gated and code secured. It has an amazing view, access to Smathers Beach...
    Reviewed 6 June 2019
    Thank you for the privilege of renting your Key West home. The unit was exceptional and LaBrisa was exquisite in every way. We could not be happier with our vacation rental. I...
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    About this property
    The 'SeaJay' at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    New Listing Family Friendly1 / 32
    (9)Excellent
    2.9 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2019
    clean and well furnished. Very responsive owner. Close to downtown Key West.We would rent this place again.
    Reviewed 23 January 2019
    We stayed with two other couples and found this to be the perfect place to stay in Key West. The home was very well equipped and felt like home. Roy went out of his way to...
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    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Comfy Family Home in a Gorgeous Gated Community1 / 12
    (4)Excellent
    2.8 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 2020
    This condo was fabulous! We had three couples and it accommodated us perfectly. The gated community was great and the pool was really fun and nice! The owner answered our...
    Reviewed 29 June 2019
    This place was really nice. Very comfortable and the pics were accurate. The community pool was also nice. The owner checked in a couple times to see if we needed anything as...
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    About this property
    Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and 2 queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    0.4 kilometres from Key West Intl Airport
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    Loved Jen and Mitch! Very welcoming! Made everything very comfortable and relaxing! Thier friends and neighbors are very nice and welcoming too! We enjoyed a cookout, a...
    Reviewed 12 April 2018
    My husband and I enjoyed a 3 day stay on the Fat and Sassy. The owners are welcoming and helpful with any questions or recommendations you it need. The marina is perfect, with a...
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    About this property
    Join us in Key West where we are docked at a beautiful Marina. Enjoy all the comforts of home and the added beauty of the Ocean. There are pools and a Waterfront Bar & Grill for your enjoyment. We will be Aboard in the private owner’s suite to make sure your stay is hassle free and exciting....
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunrise at Seaside Condo 2 Bedroom1 / 22
    (36)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2020
    We stayed at the sunrise condos for one week. Unfortunately, it was just as the state of Florida was closing everything down so we ended up spending more time at the condo and...
    Reviewed 22 March 2020
    My husband and I loved the 2-bedroom condo we rented. It was very bright & clean! We enjoyed the swimming pool each day we were there. Easy check-in and check-out. Bonnie...
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3.6 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Central Heating
    • Washer
    • Balcony
    • Patio
    • Waterfront
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.7 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Terrace
    • Central Heating
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 22
    (37)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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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 8 January 2020
    With last min booking this place, we felt lucky to find a 2 bedrooms with kitchen to host our family of 5. The condo are equipped several sets of sheets, towels, etc. washer...
    Reviewed 30 July 2019
    We had a great visit to the Keys, the condo was clean which is our number one priority and Bonnie the host was very responsive to all communication prior to our stay. Bonnie...
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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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 57
    (41)Excellent
    3.7 kilometres from Key West Intl Airport
    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 14 November 2019
    I stayed here with a group of 10 friends. 4 couples and three singles. We had the best time. The house is beautiful. The pool amazing. Abby was responsive and helpful. Our...
    Reviewed 20 June 2018
    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!
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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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    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Key West Living-Oceanside Catamaran 'Esprit du Vent'1 / 9
    (3)Excellent
    3.5 kilometres from Key West Intl Airport
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 26 March 2019
    My husband and I had a wonderful, relaxing time off the shores of beautiful Key West on the Esprit du Vent. The accommodations were very comfortable and the service was stellar...
    Reviewed 22 March 2019
    It is so interesting and fascinating being in to this wonderful place, everything is awesome about this place.
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    About this property
    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Atlantis House Master Suite1 / 22
    (25)Excellent
    2.4 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2019
    We wanted somewhere special to celebrate our 30th anniversary and did we hit the jackpot! Steve and Kayla are such gracious hosts. The key lime pie that Kayla makes is heavenly...
    Reviewed 25 November 2018
    The Atlantis House and owners Steve and Kayla are wonderful! Located just steps from one of the few beaches on the island and away from Duval Street , the master suite is a...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (9)Excellent
    3.1 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2019
    Key West Oasis is a perfect warm weather get-a-way with a very private (no view of neighbors) backyard and an enclosed outdoor shower as a plus! The house was recently renovated...
    Reviewed 27 February 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Spectacular Atlantic Ocean View Condo (MONTHLY)1 / 26
    (19)Excellent
    3.2 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 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 27 December 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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'Little Paradise' Historic Seaport Old Town Key West1 / 16
    (1)Very good
    3.5 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 February 2019
    The house is well equipped and very comfortable. My husband is disabled and the shower was perfect for him but not for someone in a wheelchair. The front steps were very hard...
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    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.4 kilometres from Key West Intl Airport
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Parking
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Spacious 3BR/3BA Catamaran as Private Sailing Charter up to 7 nights in Key West1 / 70
    (7)Excellent
    2.7 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
    • Grill
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2019
    A neighbor suggested a multi-day sailing charter for a family-oriented spring break experience in Key West and then gave us his recommendations. We started looking around in the...
    Reviewed 5 April 2019
    Had a wonderful time sailing in Key West with Tadd and Lindsay. Their nautical expertise was evident by their skillful sailing as well as their attention to detail and customer...
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    About this property
    Create lasting memories on an all-inclusive private charter boat for up to 6 people. Enjoy the unique all-inclusive vacation experience of sailing, fishing, snorkeling, scuba diving and paddling aboard our 47ft luxury sailing catamaran charter boat. Sail and play on the water all day, then sleep...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE1 / 30
    (67)Very good
    2.9 kilometres from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    This lovely condo was great for our stay in Key West. Located on Stock Island just at the entry of Key West, it was perfect for staying "out of the frenzy" of town, but...
    Reviewed 13 May 2017
    We had a great three days on the island. Condo was well equipped although we ate out or got pizza - pizza place across the road served delicious pizzas. Ther were 5 of us so my...
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    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa with a 5' thick memory...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3.7 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here your vacation dreams come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Sunny View1 / 24
    (2)Excellent
    3.3 kilometres from Key West Intl Airport
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Pet friendly
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    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
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 2 bedroom 2 bath ocean-view overlooking the famous Smathers Beach, Enjoy the balmy ocean breezes from your private balcony and watch the world go by. This unit features 2 bedrooms, one king and one queen. For your convenience there are 2 roll-away beds for extra guests. Full size...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.1 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
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    • Ocean Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southern Crosser is the latest luxuriously designed cruising catamaran from world renowned French boat builder Fountaine Pajot. ​Following her initial voyage from France to Ft. Lauderdale for commissioning, she was delivered to her new Key West home in January 2018. This brand new vessel is 3.85...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    * Book today Anchor drop key west short bike ride from old Town*1 / 28
    (5)Excellent
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2017
    The condo was exactly as it was pictured. Love the way the balcony was accessible from the living room or the bedrooms. I absolutely fell in love with the shower. The owners...
    Reviewed 15 July 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for...
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    About this property
    Anchor Drop 307 is a totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom (which can also be converted to a King bed upon request) and a queen sleeper sofa in the living room. Anchor Drop is beautifully renovated and decorated by an interior...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedroom Oceanfront Condo Key West1 / 14
    (8)Very good
    1.8 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The...
    Reviewed 29 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds...
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.3 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    2 Bed 2 Bath Waterfront Key West Condo on Smathers Beach Peaceful views and tropical breezes of the natural salt ponds, acting as a bird sanctuary for native species, will help you relax in a fully furnished and updated 2 bedroom / 2 bathroom property sitting on Smathers Beach in Key West, Florida....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    2.5 kilometres from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool. 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...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    3.7 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by. You know the feeling. Rushing to go on vacation, to the airport, driving in traffic, so many people around you doing the same thing, finally in Key West at your home...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Conch is a fantastic rental with a great location in the 1800 Atlantic Condo Complex. This unit features an extra large floor plan, both bedrooms and the living room have impact resistant sliding glass doors that open on the a large wrap around deck, you may even get a glipse of the...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    ** Totally renovated in 2019, New Kitchen & Bathrooms.. Book Now **1 / 48
    (1)Terrible
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master bedroom, 2 twins in the 2nd bedroom that can be converted to a King .memory foam luxury queen sleeper in the living room will comfortably accommodate your party. Watch the sunrise...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3.7 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Spacious 1 bedroom w/additional queen sleeper sofa for short term guests. 1st floor in Old Town. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks from seaport, 6 blocks to Duval. Granite kitchen, Washer/Dryer, outdoor propane grill, tile floors, tiled shower, central AC,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LAST MINUTE DEAL FOR NEXT WEEK (JAN 13-20, 2018). RATE DROP OF $200 FOR THE WEEK. BASE RENT IS NOW $1400. The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Beautifully appointed Townhouse with wonderful view of the Atlantic Ocean. Pride of ownership shows in every room. This unit is a monthly rental. Come to Key West and stay a while enjoy life in a lovely townhouse with an elevator to make your stay more convenient.This unit has 2 beautifully...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Atlantis House Garden Suite1 / 24
    (1)Excellent
    2.4 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2020
    My husband and I stayed in the garden suit and loved it. Capt. Steve and Kayla really put their heart into making their home comfortable and cozy for their guests. They are...
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    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.7 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 1 bedroom w/additional queen sleeper sofa. Sleeps 4 total guests. 1st floor in Old Town. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks from seaport, 6 blocks to Duval. Granite kitchen, Washer/Dryer, outdoor propane grill, travertine floors, tiled shower,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    The Blue Pelican - Comes With 6 Passenger Gas Golf Cart1 / 55
    (1)Excellent
    2.6 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 30 November 2019
    Our stay was amazing. The golf cart was a bonus no need to rent a car. Excellent pool with a wrap around garden with just enough plants to provide a tropical paradise. 3 blocks...
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    About this property
    The Blue Pelican is a brand new 1924 square foot villa in new town Key West. Monthly home rentals come with a 6 passenger gas golf cart to get you around the island, a welcome gift basket for your enjoyment and a full time concierge for all of your activity and dining requests. Featuring 3...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3.7 kilometres from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Complete renovation in a tropical modern/industrial style. Only 3 total condos on this property. Unit has its own washer/dryer. Private wrap around porches that overlook Frances Street and also the large, heated pool. 2nd floor unit offers complete privacy. A premier location near Seaport,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean1 / 19
    (17)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2019
    The condo was very nice. Clean and roomy! We had a wonderful time. Check in and out was simple and all directions were spot in
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
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    About this property
    This two bedroom, two full baths condo with kitchen and private balcony, offers all the conveniences of your own home. There is one King bedroom, one Queen bedroom and one Queen size pull out couch in the living room. Kitchen is equipped with tableware for at least six guests. Pots, skillets, and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront Oasis1 / 16
    (1)Excellent
    3.4 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2019
    This place is a hidden gem; a real oasis! It has every amenity you can think of. We got a two bedroom, 2-1/2 baths, kitchen, wet bar, great pool, beautiful restaurant, etc...
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    About this property
    A beautiful oceanfront suite located at the best marina in the Keys. Located off the azure waters of the Atlantic Ocean, minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3.0 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.9 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Hot Tub
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    • Sauna
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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