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Sugarloaf Key Vacation Rentals

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    Sugarloaf Key is popular with travelers just like you. Don’t let them get your perfect place first—book today!
    All 215 Rentals in Sugarloaf Key
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    About this property
    Spend your Key West vacation in style here at this high-end house with a private hot tub! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks away...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Bask in the allure of old town Key West at this dog-friendly condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants. Located mere steps from Duval Street and verdant tropical gardens, this Duval Square condo...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool. You'll find this comfortable condo in Duval Square, offering...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle. Located alongside several...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Swap out the winter blues for the incredible blue of Key West's sky, and book a stay in this delightful condo! With resort amenities like tennis courts, a shared pool and hot tub, and lush tropical landscaping, you'll be back in summer mode in no time. This condo is part of the upscale Sunrise...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. A convenient location by the Key West Airport - combined with shuttle service to some of the area's most...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this condo offers guests unbeatable...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    About this property
    Experience the best of the Keys during a stay in this beach home with dog-friendly accommodations (for a small nightly fee) and a private pool and hot tub! Shark Key Chateau offers room for up to 14 people, so bring the whole family along. While you'll feel like you're on your own private island,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Surrounded by possibilities for fun and relaxation, this Key West cottage offers up to four guests the chance to bask in the warm Florida sun. Featuring a private hot tub, pristine seasonally heated shared pool, and easy access to a wide range of local attractions, this home puts you right in the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex neighborhood of Key...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, and a shared pool, your vacation promises to be one to remember. This home is nestled in a quiet neighborhood,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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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 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more! Perfectly located between Truman Annex and Bahama Village, this...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    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. You're about a block away from Southernmost Point, a photo-friendly attraction and home to a gorgeous beach. Duval Street's eating and entertainment...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This dog-friendly condo accommodates up to six, so it's a great choice for the whole family! This condo backs up to a stretch of Higgs Beach, so you're never far...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unlock the secret to an incredible vacation with a stay at this charming Key West condo! Bursting with amenities like a shared pool and hot tub, tennis courts, dog-friendly accommodations, and a private balcony, this airy vacation rental is sure to delight. Located on the eastern edge of the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Immerse yourself in the island lifestyle when you book this Key West home. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Located just over three blocks from the southernmost point in the continental United States landmark,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Dreaming about a tropical vacation? This two-bedroom, one-bathroom cottage in Key West is the perfect destination - a private hot tub, garden, and a great location downtown will make this your best vacation yet! Located only half a block from the restaurants and bars on Duval Street, you'll have...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    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 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Find the ultimate in Key West charm at this sun-splashed, dog-friendly cottage with a private pool and garden, a classic wrap-around porch, and an enviable location on a beautiful, historic street. Designed in Key West's famous 'conch cottage' style, this picturesque home sits near the heart of the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex one block from the beach,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Smoking allowed
    About this property
    Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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. This cottage's location is truly stellar, just...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing cottage, everything is possible! Your new home away from home sits on a hill only a few blocks from the beating heart of Key West. Shopping, dining, and more can be...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat yourself to a much-needed getaway filled with stress-free days and sun-soaked afternoons when you book your escape to this Key West retreat. Offering the chance to enjoy a private hot tub, street parking, a shared pool, and easy beach access, this home will make sure your stay is one to...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dip your toes in the sand and revel in long lazy days on the beach when you book your vacation to this Key West condo. Boasting room for up to four guests, a covered parking spot for one car, a shared pool, and a location that puts you in the heart of it all, your vacation promises to be one to...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Bask in the tropics of Key West at this dog-friendly cottage with a private heated pool and a lush backyard garden. This lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square. Stay cool with air conditioning,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private pool, luxurious patio area, covered porch,...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pamper yourself with a stay at this luxurious dog-friendly Key West condo! In addition to comfortable furnishings and a terrific location, this elegant rental includes first-rate amenities like a shared pool and hot tub, a tennis court, and a reserved parking space. Located on the warm waters of...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    If Key West is on your travel itinerary, make this lovely dog-friendly 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...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Luxury and convenience combine in this recently renovated one-bedroom, one-bathroom condo in Key West. You'll love the shared pool, full kitchen, and various entertainment close to all the excitement of downtown! Sitting on the uppermost floor of a building surrounded by palm trees, you'll...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grab your sunglasses, pull up a lounge chair, and relax beside the lagoon-shaped community pool at this upscale Key West condo! From gorgeous tropical landscaping to a private balcony and a dog-friendly policy, this comfortable rental has everything you need for the ultimate Key West experience....
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Washer
    • Balcony
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    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    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 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privacy meets convenience at this beautiful Key West vacation rental, which features a two-bedroom, two-bathroom home, a separate studio cottage, a private pool, and room for up to eight guests. This recently renovated vacation rental sits just off Duval Street, putting you within easy walking...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West, where your balcony overlooks the colorful main drag! This home has dog-friendly accommodations for a small nightly fee. This condo faces historic Duval Street, where you'll find some of Key West's most exciting shopping and dining. Walk three blocks to the...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat your loved ones to a trip to the Florida Keys they'll never forget! With two bedrooms and bathrooms, you can be sure everyone in your group will enjoy the local sights and sounds in comfort. This condo is located in the Sunrise Suites Resort and offers a complimentary shuttle that will take...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The tranquil majesty of Key West will be at your fingertips when you stay at this homey two-bedroom, two-and-a-half-bathroom condo, with a shared pool and a great location near the beach! Part of Banana's Foster Guest House in the center of downtown, you'll be within easy walking distance from...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step out on the deck of Mary's Trio and breathe in the beach breeze! This well-furnished home provides plenty of space to relax - ideal for families or large groups. You're within walking distance of the docks, as well as nightlife like Dante's. Stop by Cuban Coffee Queen for a cafécito, and be...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to the Keys for your next Florida getaway and set yourself up for comfort and convenience when you stay at this welcoming, well-equipped home with a private pool and charming covered porch. You'll be situated only a mile from South Beach, so the sand and water are always within easy access. A...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the laid-back ambience of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time. This two-bedroom...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the tropical warmth of Key West at this two-bedroom condo, where you'll enjoy a beautiful community swimming pool, a private patio dining area, and an outstanding location close to beaches, shops, and restaurants. This condo is located in the lovely Truman Annex neighborhood, offering...
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    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Hot Tub
    • Grill
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    • Cable/satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation in style and comfort at this charming, dog-friendly Key West home just steps away from the 18-hole Key West Golf Club. Whether you're teeing up for a leisurely day on the course, enjoying the ocean breeze from your front porch, or exploring the island's beaches and marinas, this colorfully...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Patio
    • Cable/satellite TV
    • Parking
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy Key West rental comes with a shared pool (complete with a cascading waterfall), a furnished patio area, and space for up to six guests. It's perfect for that next family vacation or tropical getaway with a few friends. Please note that this home also comes with one private, off-street...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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