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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 December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool1 / 29
    (4)Very good
    0.3 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Colorful condo w/ deck, balcony & shared pool - near downtown & beaches1 / 27
    (23)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Comfortable condo living w/ shared pool & lush gardens - in Old Town, dogs ok1 / 25
    (21)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Dog-friendly condo w/ private hot tub & shared pool - close to shops & beaches1 / 26
    (16)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Parking
    • Air Conditioning
    • Hot Tub
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find a cool, comfortable retreat at this dog-friendly Key West condo, a well-equipped getaway with a private deck and balcony, access to a community swimming pool, and a wonderful location near the heart of the old town. This condo sits among tropical gardens in Duval Square, a location with...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Grill
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where you can enjoy galleries, shops,...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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
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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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    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
    • Washer
    • Cable/satellite TV
    • Patio
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    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
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style during your visit to Key West - this home offers a private parking spot, an upstairs deck, dog-friendly accommodations, and plenty of space for your group to relax. Enjoy a full kitchen, free WiFi, and a pull-out bed at Duval Delight. At this home, you're on the end of historic Duval...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Six dog-friendly homes in a quiet neighborhood w/ private pool & hot tub1 / 25
    (1)Excellent
    0.3 kilometres from Southernmost Point
    12 Bedrooms, 9 Bathrooms, Sleeps 36 Quick View
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    • Hot Tub
    • Patio
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're planning your next family friendly group getaway or a large family reunion, this grouping of six separate Key West homes is the perfect spot for everyone to spread out and enjoy some privacy in a quiet residential neighborhood. Featuring street parking, a private pool, hot tub, grilling...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 12 Bedrooms, 9 Bathrooms, Sleeps 36
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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
    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    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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    Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!1 / 27
    (12)Very good
    0.6 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no...
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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
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Hot Tub
    Suitability
    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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    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional nightly fee....
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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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
    • Cable/satellite TV
    • Hot Tub
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    • Patio
    Suitability
    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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    0.0 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four-bedroom Key West home has just what you need for an awe-inspiring Florida beach getaway, including a private heated pool, rooftop patio with a fantastic ocean view, and easy access to the beach and major attractions. You'll be a few steps from Southernmost Point, and you can walk to Key...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
    • Air Conditioning
    • 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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    Stock Island, Florida Keys
    Holiday Rental House - 3 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
    • Grill
    • Hot Tub
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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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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Internet Access
    • Balcony
    • Parking
    • Grill
    • 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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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Bright, clean home w/private hot tub & shared pool, close to everything, dogs ok1 / 27
    (13)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    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, this rental is perfect for those looking to enjoy a little fun in...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 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
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    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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    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.3 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Internet Access
    • Parking
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The sunny paradise of Key West beckons, and this dog-friendly home is the perfect place to stay, with a private patio and hot tub ensuring relaxation is never far away. Located just steps from desirable Duval Street, this home makes it easy to experience all the best attractions in Key West, from...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 26
    (29)Very good
    0.6 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the tropical ambience of this studio-style Key West cottage, where you'll find a private patio, dog-friendly accommodations, and a perfect location for dining, shopping, and exploring the local beaches and nightlife. This sweet yellow cottage is located in Simonton Court, a complex that sits...
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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Key West for a sun-filled getaway and stay in this lovely two-bedroom retreat with a private pool for an unforgettable reprieve from life's hectic pace. Bring the dog along for a small nightly fee and revel in your close proximity to famous Duval Street and more! You'll be situated in the...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
    • Air Conditioning
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    • Cable/satellite TV
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this stylish, three-bedroom, two-and-a-half bath home for six yours when you come to Key West, and revel in amenities like a private heated pool and an ideal location. Located in downtown Key West, this home is a mere one block from Duval Street. Southernmost Point and Beach and the...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • 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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    0.1 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Hot Tub
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    • Parking
    • DVD Player
    Suitability
    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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    0.3 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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    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
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    • Air Conditioning
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    • 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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    Lovely, dog-friendly townhouse w/ private pool, full kitchen & beach access1 / 25
    (21)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    You'll settle into island life instantly at this two-bedroom, two-and-a-half-bathroom townhouse in Key West. With a private pool and lush garden in the backyard, a full kitchen, and a great location near the beach, comfort is never far away from your explorations. Located on the south end of the...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 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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    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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    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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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    • Terrace
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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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    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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    0.5 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    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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    Cozy, dog-friendly townhouse w/ shared pool & courtyard - walk to Duval & more!1 / 26
    (24)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Condo on Duval w/shared hot tub  & private parking - dogs OK1 / 29
    (34)Very good
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind in the heart of Key West's historic district with a dip in condo's hot tub ! The back patio here offers room to grill out and relax with your group after a long day enjoying all the island has to offer. This suite is located on historic Duval Street, where you'll find some of Key West's...
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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 3 Quick View
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    • Internet Access
    • Balcony
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore Key West with this conveniently located, dog-friendly condo as your home base! Duval Street's famous array of bars, shopping, and eateries is just outside your door. Explore the neighborhood's historic sights like the Ernest Hemingway House, about five blocks away. Stroll four blocks the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    Suitability
    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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    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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    Suitability
    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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    0.2 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
    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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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Suitability
    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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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Condo in historic district w/shared hot tub  - 2 blocks to ocean, dogs OK1 / 28
    (24)Very good
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Here in the heart of historic Key West, you'll have access to a shared hot tub, dog-friendly accommodations, and grill on your backyard patio area, as well as private parking! From here, you're only two blocks from the beach at Fort Zachary Taylor State Park. Duval Street's restaurants, bars, and...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    • Internet Access
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    Pet friendly
    Kid friendly
    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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    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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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Cozy, dog-friendly condo with views - walk to beach, dining, & attractions1 / 33
    (6)Average
    0.5 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Key West for a romantic getaway for two and walk to the beach, dining, and other attractions when you make this cozy, efficiency studio yours. You'll be located in a quiet neighborhood and surrounded by tropical vegetation and decking for great views. You'll be within walking distance to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.2 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
    Your island escape will be worth dreaming about when you stay at this affordable studio in central Key West. With a shared balcony for relaxing among the palm trees, dog-friendly accommodations, and beach access nearby, you'll be basking in paradise every second you're here! Located on Duval...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming, dog-friendly home in a residential neighborhood w/ shared pool1 / 29
    (8)Very good
    0.3 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect romantic escape for your next getaway, then look no further than this romantic Key West cottage. Featuring room for two guests to enjoy a shared pool and a location that puts you within easy reach of all of the local attractions, this is the perfect spot for a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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