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Holiday Rentals in Stock Island

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    All 56 Rentals in Stock Island
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You are so close to the large community pool that you will be able to hear the waterfall in this beautifully landscaped area. This is a very unique home where the original owner has kept this little treasure all to herself and now wants to share it with you! An accomplished artist, the home is...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    In the heart of downtown Key West easy walking to great restaurants and shops. Living at Ground Zero was never so easy. This 2-bedroom home is steps away from the historic Mile Marker 0 that marks the beginning of federal highway U.S. 1 (which continues up the East coast 2400 miles away ending in...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Terrace
    • Balcony
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point. This timeless private conch home just steps away from the Hemingway House and the Key West Lighthouse a perfect location to be...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique 1 bedroom, 2 bath cottage is about to become your home away from home! Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE! This spacious cottage with a large private covered deck, just perfect for enjoying an afternoon cocktail or a...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space. A quintessential cigar makers shotgun style house built circa in 1890s. Located in one of the most desirable historic neighborhoods of Key West – The Meadows with tree-lined...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Waterfront
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    • Ocean Views
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will not find a nicer or cleaner yacht than this in Key West. This almost new, luxury, yacht has a large great room and kitchen area with windows surrounding it 360 degrees making views of the ocean amazing. It has a three bedroom layout with each bedroom having its own private bathroom and...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Private conch home in a quiet neighborhood but still within walking distance to all of the Key West sites. Here's a little gem in a long-established local residential neighborhood just across from the Key West historic cemetery (quiet neighbors). Spacious downstairs with living/dining area that...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4BR/1.5BA tropical retreat is situated in a lush gated community, enveloped by Spanish lime trees, hibiscus, orchids, and a wide variety of beautiful species and exotic palms. In a prime locale, you’ll be within minutes of everything Old Town Key West has to offer. Walk to the beach or hop...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wow, yes a super cool unique opportunity to stay aboard a yacht. All yours, this huge 70 foot mega yacht in Key West, Florida and you can have her all to yourself’s, private with a 2 day min stay. I stay nearby on my other vessel that I use for snorkel/sunset trips or if you need assistance...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Balcony
    • Washer
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Situated in the exclusive gated enclave of Old Town Villas at Key West, this stunning brand-new 3BR/3.5BA townhome offers a private elevator, patio, five balconies, and community pool access. Relax in one of two living rooms with large HD TVs, or simply watch the sun set from the...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
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    • Grill
    • Terrace
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool. Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool. Poolside Paradise was built with entertaining in mind. Privacy fence surrounds the intimate front yard perfect for gathering, wet bar is welcome addition in the kitchen,...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard. This classic 3-bedroom Conch home is located across the street from Bayview Park, with tennis courts, playground, basketball court and community activities. Built in...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Expansive group escape w/shared pool & five separate villas 1/2 block from Duval1 / 41
    (1)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 11 February 2015
    I stayed here with a group of friends and we reserved all five of the villas for 14 people. Each villa had one bedroom and most had one and a half bath with a small kitchen that...
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    About this property
    This family-friendly Key West home features five separate villas grouped together, a shared pool, and a location that puts you close to all of the action. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located on Center Street, this home is just a mile from the Key West...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 20
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Balcony
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home! Located in the private, gated community of Coral Hammock which is a short car ride away from downtown of Key West. Conveniently located just down the street...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Balcony
    • Internet Access
    • Washer
    • Waterfront
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the privacy that this waterfront condo has to offer during your next vacation to Key West. This condo is perfectly situated off the beaten path and in a private gated community. Beat the heat by relaxing in the shared pool or with the central A/C inside. The shared hot tub is another place to...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant, upscale home w/ heated pool moments from beach!1 / 29
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Grill
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    • Cable/satellite TV
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    • Balcony
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave behind all of your worries and whisk your loved ones off to this two-bedroom, two-and-a-half bathroom home on Sunset Key! This private island home surrounds you with nothing but natural beauty, gorgeous beaches, and high-quality amenities. Your home is nestled on the private island of Sunset...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in one of the most sought out neighborhoods 'The Meadows' this lovely condo has everything you need to enjoy your time in Key West. Nestled in the ever popular local residential neighborhood known as The Meadows, this sweet spot is a 2-bedroom 2-bath upper level condo in a home with a...
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    Stock Island, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment. Relax on your balcony overlooking the saltwater pool with palm trees swaying in the breeze, a perfect picture? This lovely 2 bedroom 2 bath upstairs condo is just that. There...
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    Stock Island, 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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    • Air Conditioning
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    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home. Ocean views and tropical breezes await your arrival to this 2 bedroom 2 bathroom condominium with wrap around balconies on the 3rd floor of the condo building. Suited for 4 people with two King...
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    Stock Island, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Waterfront
    • Hot Tub
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront condo, located within a gated community, boasts incredible views of the water and spectacular sunsets. With a private, furnished balcony overlooking the marina and a shared hot tub and outdoor pool, this condo is ready for your next family vacation in the Florida Keys. What's...
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    Stock Island, 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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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautifully remodeled home with quaint charm and colorful front and back porches. Take in the lush landscaping that surrounds the one-of-a-kind lazy river heated pool, or relax in the well-designed interior. This home features Key West flair, two workstations, two bicycles, ceiling fans,...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Private Outdoor Pool (Heated)
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Oceanside at 1800 Atlantic is a 2 bedroom 2 bath monthly rental. The property is in an excellent location in the complex facing the tropical gardens. This Property can be your home away from home with all the modern amenities you desire. South Oceanside is tiled throughout and freshly...
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    Stock Island, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool, a Jacuzzi tub, and a balcony with sweeping ocean views. You'll be centrally located in the heart of Key West in the exclusive Key Cove community. Walk to grocery stores and a...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play. You're located on...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready to see a whole new side of the sunshine state from the comfort of this home in Key West. You'll enjoy perks like a private pool, as well as a great location just a few blocks from the beach! Nestled on the eastern edge of Key West, this home is a short walk from the soft sands of Higgs...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Couple's dog-friendly getaway with central location and access to a shared pool1 / 26
    (39)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    Reviewed 28 February 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
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    About this property
    Book your romantic escape to this dog-friendly Key West home. With access to a shared pool and a great location on Duval Street, you'll be able to slip into vacation mode in no time. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am This home is just a block from the Ernest...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 27
    (33)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 16 August 2017
    We LOVED our stay at the Andros Suite! The condo itself was clean and comfortable. The courtyard was breathtaking! The couple that are the property managers are PHENOMENAL...
    Reviewed 20 May 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected...
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    About this property
    Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice: This is in a residential area, Quiet Hours...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 30 October 2015
    This is our second year at this location. This year we chose the Havana Suite. The unit was extremely clean and pleasantly decorated. Very nice kitchen. TVs in the bedroom and...
    Reviewed 27 April 2015
    We chose Little Havana initially because of the location. It is a smidgen off the beaten path from the hustle and bustle of the Duval action, yet within walking distance to a...
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    About this property
    Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free! Notice: This is in a residential area, Quiet Hours...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this classic Key West cottage featuring a shared pool and a furnished patio, located within blocks of beaches, shops, restaurants, and museums! You can even bring the family dog for a small nightly fee. If you're here for the sand and sun, several local beaches are located less than a mile...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this elegant, waterfront rental in Key West serve as home base for your next Florida vacation, and enjoy a private pool and covered deck with ocean views, among other fine amenities. The rental is located in the private community of Key Cove Landings within walking distance to the essentials...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy Key West rental is ready to be your home away from home! Located on a tree-lined street in the Truman Annex community, this townhouse offers a full kitchen, patio, and a shared pool. Just a half-mile away, experience the excitement of Duval Street for shopping, dining, and entertainment....
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury awaits in this cozy yet spacious four-bedroom, four-bath Key West home, featuring a private pool and Jacuzzi, as well as close proximity to all the major locations. It's ideal for multiple families and large groups offering accommodations for up to 10. You'll enjoy the out-of-the-way...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Romantic dog-friendly cottage w/shared pool, tropical decor, & easy beach access1 / 26
    (25)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    Reviewed 19 August 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    About this property
    Book your romantic retreat to this dog-friendly Key West cottage. Enjoy the shared pool and a great location off of Duval Street. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located a few blocks from the Florida Keys National Marine Sanctuary and just a half a mile to...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Internet Access
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    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely four-bedroom, four-bath home for 10 provides a prime location and excellent amenities, including a private pool, a Jacuzzi, and a covered balcony with sweeping ocean views. You'll be located on the north side of Key West in the exclusive Key Cove community. Walk to a shopping center,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Cable/satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four-bedroom, three-and-a-half-bath Key West home has a private heated pool, a covered lanai, and an upper deck, as well as beautiful views from every window. It's situated in the exclusive Key Cove Landings, right on the water and within walking distance to grocery shopping, restaurants, and...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unbeatable location of this two-bedroom, dog-friendly Key West townhouse. This home features four covered balconies, including one that overlooks the community pool and central courtyard. Ceiling fans and central A/C keep the Florida heat at bay, while the private grill is great for a...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West. This home...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Terrace
    • Washer
    • Air Conditioning
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    • Cable/satellite TV
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway! What’s nearby: Located right near the water, you’ll be in a prime spot to sample all of the island's many charms....
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    Location Information
    Stock Island, 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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    • Washer
    • Cable/satellite TV
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    • Internet Access
    • Air Conditioning
    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the incredible location and amenities of this Key West condo. The central A/C and shared pool help keep the heat away, while the shared hot tub is a great place to spend cooler evenings. What's Nearby: This condo is tucked away from the hustle and bustle, but still within walking distance...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stunning home near beach and town with private hot tub and shared pool - dogs OK1 / 24
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
    Reviewed 23 January 2014
    Tobago House is very nice, close to Duval - quiet street.Nice amenities, pool, hot tub, great outdoor area. Would recommend to anyone. Close walk to everything.Wonderful!
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    About this property
    Make your next stay in the Florida Keys one to remember with this amazing home in Key West! Three bedrooms, three bathrooms, dog-friendly accommodations, and a shared pool ensure your next trip to the tropics will be one you'll always remember. Your home is only a block away from the famous shops...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cozy, dog-friendly townhouse w/ shared pool & courtyard - walk to Duval & more!1 / 26
    (24)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    What a beautiful place, the court yard was unbelievable all the love and care that has gone into all the plants, so peaceful to sit and relax and regroup from the Key West...
    Reviewed 1 June 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space...
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    About this property
    Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Park your car on the street and walk...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Air Conditioning
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soft sands, cool drinks, and breathtaking sunsets are at your fingertips at this Key West condo. You'll be moments from beaches, bars, and restaurants, with shared perks like a pool and hot tub waiting back at the building! You and your loved ones will love this home's location on Stock Island,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unbeatable location of this Key West studio. A ceiling fan and window unit A/C helps keep the Florida heat at bay, while the shared courtyard and covered porches are a great place to enjoy the evenings. What's nearby: This cozy studio apartment is located in a quiet neighborhood with...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Internet Access
    • Balcony
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    • Grill
    • Terrace
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to paradise at this family-friendly, three-bedroom Key West townhouse with a full, modern kitchen, furnished deck, and a shared on-site pool - all close to shops, beaches, and local attractions. This townhouse is within walking distance of many of Key West's most popular destinations,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget. Located steps from the intersection of Truman Avenue and Whitehead Street, this...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    • Balcony
    • Patio
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    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning property overlooking the Gulf of Mexico boasts panoramic views from nearly every room and the private pool. Designed with hand scraped bamboo floors and a beautiful wraparound deck with several different seating options, this waterfront home is perfect for families or group getaways....
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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