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Holiday Rentals near Southernmost Point

Whitehead Street, Key West, Florida 33040
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    Travellers to Key West are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Dog-friendly condo w/private hot tub & shared pool - walk to Duval St!1 / 29
    (36)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    0.2 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    0.3 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 32
    (7)Very good
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Duval Square1 / 22
    (49)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
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    • Patio
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax1 / 27
    (3)Excellent
    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ibis Suite offers visitors a prime location in Old Town Key West, great amenities, and space to relax. Top off your visit with soaking time in one of the property's hot tubs, and you're well on your way to an optimal Key West experience. Here, you're a few blocks off of famous Duval Street, home...
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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Quiet, dog-friendly getaway in a residential neighborhood with a shared pool1 / 24
    (4)Excellent
    0.3 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to experience the best of...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 1,500 sq. ft. townhouse with 2 large bedrooms with king beds, 3 full bathrooms plus covered deeded parking for your car. Fully equipped kitchen. Sleeps up to 6 comfortably as the downstairs living room has a queen sleeper and full bath. Luxury furnishings and appliances throughout make this...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Colorful, dog-friendly cottage w/ private pool & all the comforts of home1 / 30
    (8)Very good
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Terrace
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a quintessential Key West vacation when you stay at this historic three-bedroom, two-and-a-half-bathroom cottage. With a private heated pool, home comforts including free WiFi and cable TV, and room for up to eight guests, this home is perfect for a large family or a group of close...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok1 / 33
    (50)Very good
    0.2 kilometres from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Four dogs are...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Key West Dreamin' ~ Weekly Rental1 / 20
    (12)Very good
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Patio
    • DVD Player
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious, dog-friendly rental w/ three hot tubs, near Duval Street and the beach1 / 49
    (2)Very good
    0.1 kilometres from Southernmost Point
    6 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Patio
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gather your group at this festive property, home to three private hot tubs, deck space, multiple kitchenettes, and six bedrooms for up to 24 people. The family dog is also welcome to join you for an additional nightly fee. You're about a block away from Southernmost Point, a photo-friendly...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 24
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    Dog-friendly condo w/ porch & Old Town location - walk to beaches & restaurants!1 / 26
    (25)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy one of the most enviable locations in Key West when you escape to this two-bedroom condo, where you'll have a dog-friendly interior, a private covered porch, and wonderful access to beaches, restaurants, and the Old Town. This gated property sits in the heart of Old Town Key West, just one...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This two-bedroom, one-bathroom house is the perfect place for your next family vacation to the palm-tree paradise of Key West! With a great location downtown, a private parking space, and easy access to a sandy beach nearby, you'll be all set for fun in the sun. Located a half block from bustling...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Key West's historic district from the comfort of this condo! An upstairs balcony gives you a bird's eye view of the town, and you'll be steps away from shopping, dining, and the beach. Guests staying at this suite will experience historic Duval Street up close, from fine...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip into vacation mode as you explore Duval Street and dive into the beach scene when you book your trip to this dog-friendly Key West cottage. Featuring street parking, a relaxing shared pool, and a location that puts you right in the heart of the action, up to six guests and a canine companion...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spa On Duval1 / 24
    (6)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful vacation rental is located in the heart of Old Town, close to everything Key West has to offer! Is a tropical two story, 2 bedroom 2.5 bath Old Town Key West condo located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants,...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cute, dog-friendly condo w/ shared hot tub in the heart of historic Key West!1 / 25
    (2)Very good
    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Settle in at this conveniently located four-person suite, where you'll have access to a shared hot tub and your own kitchenette! Egret Suite can be rented on its own, or as a part of the entire property for larger groups. The family dog is also welcome to join you for an additional nightly fee. At...
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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Twice as Nice ~ Weekly Rental1 / 17
    (4)Excellent
    0.1 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Vintage Luxury Cottage ~ Weekly Rental1 / 11
    (6)Very good
    0.3 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Cable/satellite TV
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    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next family getaway. Spacious enough for up to eight guests and a dog (for a small nightly fee), this home comes with a tropically-landscaped back yard and a private, outdoor hot tub. This...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bright, clean home w/private hot tub & shared pool, close to everything, dogs ok1 / 32
    (13)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy, well-appointed condo offers easy access to Duval Street and all of Old Town Key West. Featuring private, furnished patios, an outdoor hot tub, a gorgeous shared pool, covered private parking, and room for up to six guests (four adults, comfortably), this rental is perfect for those...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Trade in the daily grind for sugar-sand beaches and gentle ocean breezes when you book your getaway to this lovely Key West cottage. Featuring a private parking spot and a bubbling hot tub, stress won't stand a chance. Located just a mile from Fort Zachary Taylor Historic State Park and a little...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your romantic getaway to this beach condo steps away from Key West's famous beaches, restaurants, and landmarks! The Salvador Dali Suite offers a central location and dog-friendly accommodations. You're situated in the heart of town, so local eateries like Banana Cafe, about a quarter-mile...
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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Cable/satellite TV
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This dog-friendly suite provides everything you need for a couple's getaway in Key West. This home's coveted location on Duval Street means prime access to the town's best nightlife and restaurants, like Nine One Five a few blocks away. You're also a short walk from the beach here: Southernmost...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cockadoodle Cottage ~ Weekly Rental1 / 10
    (4)Very good
    0.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly Key West cottage with a private hot tub & an unbeatable location!1 / 26
    (10)Very good
    0.3 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
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    • Hot Tub
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your vacation days snorkeling in the clear coastal waters and strolling the streets of downtown Key West when you stay at this three-bedroom, two-bathroom cottage, which also features a private hot tub and one reserved off-street parking space. The family dog is also welcome to join you for...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dog-friendly beach suite w/ shared hot tubs, kitchenette, patio space, and more!1 / 29
    (6)Average
    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Look no further than this homey suite for your next couple's weekend! Take a dip in the property's shared hot tubs, or simply enjoy the fresh air on the patio space outside your doorstep. Seagull Suite situates you walking distance from historic Duval Street's attractions, from dining like Blue...
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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Enchanting seaside cottage w/private pool, off-street parking, & prime location1 / 24
    (6)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come explore the rich history, decadent beaches, and seaside dining spots when you book your getaway to this Key West cottage. Filled with charm for up to five guests to enjoy, this home offers off-street parking, a private pool, and a location that puts you close to all of the beach action....
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Key West Spa Villa ~ Weekly Rental1 / 22
    (7)Average
    0.2 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    • Cable/satellite TV
    • Patio
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.3 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home for six. Dogs are also welcome for a small nightly fee. This rental is located in the heart of Old...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street1 / 24
    (4)Very good
    0.2 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This second-floor studio has a private outdoor seating area and plenty of space for up to four guests. Spend time at home splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood, this rental is just a short walk from Duval Street for the area's best...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 27
    (33)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Charming, dog-friendly condo w/ balcony & full kitchen - great central location!1 / 27
    (1)Excellent
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak up the sun and kiss your stress away at this welcoming dog-friendly condo on Key West. The peace from the balcony will inspire your dreams for months to come! The central location makes for a convenient home base, whether your plans include a visit to the Butterfly Conservatory, The Hemingway...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Duval Street Suite1 / 22
    (45)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Southernmost Point
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
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    • Grill
    • Hot Tub
    Suitability
    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away in the trees, this Key West hideaway is a great choice for couples or small families. Shared hot tub access and patio space will have you feeling right at home in Pelican Suite! Take a walk a couple blocks down and you're at the beach, toes in the sand. Local staple Louie's Backyard...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Quaint romantic cottage with street parking, close to the beach & adventure!1 / 24
    (49)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 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
    Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you right in the middle of the action while surrounding you with relaxation, this home offers room for two and street parking for convenience. Located just a block from the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.3 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Balcony
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    • Terrace
    • Air Conditioning
    • 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stunning home near beach and town with private hot tub and shared pool - dogs OK1 / 24
    (5)Very good
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
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    • Washer
    • Patio
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Internet Access
    • Hot Tub
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Heron Suite's hot tubs access, back patio space, and proximity to the beach set the tone for a lovely stay in Key West's historic district! Well-outfitted for a couple's getaway, this suite offers an excellent location paired with the amenities of home. The family dog is also welcome to join you...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental1 / 14
    (5)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
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    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably) and your dog. Stroll to shopping, entertainment, and beaches, all within a few blocks of this rental....
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.5 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    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
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.5 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Internet Access
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring some sunshine and fresh ocean air into your next romantic getaway with this cozy Key West home. You'll enjoy a great location right at the center of the action, with a uniquely decorated and vibrant atmosphere awaiting you back at home! Right off Truman Avenue, this condo for two lies steps...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.3 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take advantage of all that Key West has to offer from the incredible location of this adorable Key West home. This home features a full kitchen, clawfoot bathtub, front porch, unique french doors, hardwood floors, and plenty of Key West charm. Enjoy your next trip to the Florida Keys from the...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Expansive group escape w/shared pool & four separate villas 1/2 block from Duval1 / 41
    (1)Excellent
    0.5 kilometres from Southernmost Point
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Internet Access
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    • Cable/satellite TV
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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