Home Vacation Rentals By Owner In Key West, FL

Showing 240 Of 1997 Vacation Rentals
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Exceptional(6)

$190.26

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Private Vacation Home

Waterfront, Single-Story Home on a Canal w/ Dock, Kayaks, AC - 1 Small Dog OK

Key West, Florida, United States

Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story home provides a canal-front dock where you can park your boat, two kayaks to take out each morning, and incredibly close proximity to open water two doors down. After a day spent boating and fishing, you can rinse off in the outdoor shower, toss the day's swimsuits in the washer/dryer, and cool of in the bright, tiled, and air-conditioned living space. There's a gas grill on the patio to sear your fresh catch for dinner, a fully appointed kitchen where you can prepare all the side dishes, and a lovely screened-in porch where you can dine al fresco, sip cocktails, and enjoy the glow of the sunset. Use the free WiFi to make plans for tomorrow's adventures, gather around the flatscreen TV in the living room for movie night, and sleep soundly in one of three bedrooms. The master suite features a king-size bed, sliding doors that open to the patio, and an en suite bathroom. The second bedroom has a queen-size bed and the third has two twin beds; the two rooms share the hallway bathroom.br brWhat's nearby:brThis canal-front home is located in a great neighborhood of Big Coppitt Key, with a number of eateries and conveniences a few blocks away on Overseas Highway. The heart of historic Key West is an easy, nine-mile drive west, where you'll find such legendary attractions as the Key West Historic Seaport, the Ernest Hemingway Home and Museum, Southernmost Point, Mallory Square, and the lively shops, restaurants, and bars that line Duval Street.brbrThings to know:brFull kitchenbrOne small dog is welcome for a nightly feebrConstruction equipment/vehicles are prohibited from being parked on sitebrNo smoking and no parties, pleasebrThere is a 28-night minimum stay for this propertybrbrThis property is managed by Seven Keys Vacations by Casago.
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Exceptional(10)

$171.68

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Private Vacation Home

Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything

Key West, Florida, United States

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*brbrIf Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island!brbrYou'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well as all the well-known sites, including famous Duval Street. Take a stroll to Ernest Hemingway House and Museum then head to Southernmost Point Beach for an afternoon of lounging on the sand, soothed by the sound of the crashing waves. Fort Zachary Taylor Historic State Park and the National Marine Sanctuary are a mile to the west, and Mallory Square, which offers more shopping and dining, is a mile to the north. The family dog is also welcome to join you here for an additional nightly fee.brbrAfter a fun day of exploring, head home to your tastefully decorated getaway to freshen up, then treat yourself to a mouthwatering seafood dinner at The Little Pearl. Or stay in and work your magic in the full kitchen and enjoy your feast at the small dining table or relax in the living room and watch some a cable show or movie on the flatscreen. The free WiFi will help you get around and create your ideal itinerary, and the private washer and dryer will keep your clothes and humble abode sand free.brbrBook this adorable home today, and get ready for your rejuvenating Key West getaway!brbrThis property is managed by Seven Keys Vacations by Casago.
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Exceptional(127)

$387.53

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Condo

Resort suite with pool, hot tub, tennis & full kitchen

Key West, Florida, United States

Exquisite 2-bedroom condo that has been extensively updated and completely remodeled, featuring beautiful new vinyl plank flooring, stainless steel appliances, granite countertops, and fully renovated bathrooms, along with many additional upgrades. New photos coming soon!brbrMake those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from start to finish. One dog is allowed.brbrThis rental is part of the exclusive Sunrise Suites Resort, conveniently located only a short drive from the Key West International Airport on the east side of the island. With a covered parking spot, bicycle rentals, it's easy to reach Key West's most popular attractions in just a few minutes! Stroll along the historic boardwalk, try to spot Cuba from the Southernmost Point, or go snorkeling through the island's colorful coral reefs.brbrIf you'd rather stay closer to home, you'll find plenty at the resort to keep you entertained. Take a nap in the shade of a palm tree beside the lagoon-shaped pool, sink into the bubbling waters of the community hot tub, or get your heart rate going in the fitness room. Upstairs, you'll find cable, free WiFi, and a fully equipped kitchen for your use, along with a private balcony for relaxing on. With tropical landscaping at every turn, you'll never be far from Key West's beautiful scenery.brbrYour next favorite vacation is waiting! Book your reservation today.brbrTHINGS TO KNOW
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Exceptional(1)

$230.47

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Condo

Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views

Key West, Florida, United States

Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexico, plenty of room for you and your loved ones to relax, and an ideal location close to Key West's most beloved attractions. At the end of each beautiful day, mix up a favorite beverage at the wet bar, step out onto the large balcony overlooking the Gulf, and take in one of the breathtaking sunsets Key West is known for.brbrTarpon Watch is part of Sunset Marina Residences, a gated Gulf-front community on Stock Island, also known as 'the new Key West.' On the grounds, you'll have access to a waterfront pool and hot tub, a long meandering dock for wildlife-watching, and a dedicated parking space in a covered garage (along with ample visitor parking). For boating or fishing, feel free to inquire for details about boat rentals/slips. Or, simply drive or hop in an Uber to Old Town or Smathers Beach.brbrNewly and beautifully renovated throughout, this first-floor condo is full of bold colors, comfortable furnishings, and elegant finishes. There are thoughtful touches at every turn, including a well-equipped kitchen with stainless steel appliances, a wet bar with a wine fridge for evening cocktails, and TVs in the living room and both bedrooms. Each bedroom is paired with its own bathroom, including a primary suite with a walk-in closet, both a shower and a jetted tub, and direct access to the balcony.brbrBonus features of the condo include a sleeper sofa in the living room, a private washer/dryer to help you pack light, and central air conditioning and heating to keep you comfortable all year round.brbrThings to Know:brStreaming services are available with guests' own account credentials.brCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brThis property is managed by Seven Keys Vacations by Casago.
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$241.45

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Private Vacation Home

Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach

Key West, Florida, United States

Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West.brbrThis home lies just two blocks away from Higgs Beach and the Edward B Knight Pier, putting you in a prime location to enjoy one of Key West's best stretches of surf and sand. You'll also be just over a mile from many of Key West's most popular attractions, including the Southernmost Point, the Ernest Hemingway House, and the island's many bars and restaurants.brbrBack home, escape the crowds with a relaxing soak in your private pool, then mix yourself a tropical cocktail and stretch out in the hammock for a lazy afternoon nap. When you get hungry, wander inside to fix dinner in the fully equipped kitchen, then enjoy your meal out on the deck or in front of the flatscreen TV. Free WiFi, central A/C, and a private washer/dryer are also provided for your convenience.brbrThere's no better way to experience Key West than a stay at this first-class home. Book today!brbrThings To Know:brThis property is managed by Vacasa Florida LLC.brPlease note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.
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Exceptional(124)

$391.53

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Condo

Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking

Key West, Florida, United States

Welcome to Sunset Suite -- Catalina Suite 311, your slice of paradise in vibrant Key West! This inviting two-bedroom condo is part of the upscale Sunrise Suites Resort, where tropical comfort meets resort-style amenities.brbrStep onto your private deck to soak in the island breeze, then spend your day swimming in the heated pool, unwinding in the hot tub, or hitting the on-site tennis courts and fitness center. With marinas, beaches, Old Town shops, and Key West's lively dining scene just minutes away, every day can be as relaxing—or adventurous—as you choose.brbrInside, Sunset Suite -- Catalina Suite 311 offers all the comforts of home, including central AC, free WiFi, cable TV, and a fully equipped kitchen. Two spacious bedrooms ensure restful nights, while on-site parking and elevator access make getting around a breeze. Even better, your pup can join the fun—this condo is dog-friendly for a small nightly fee.brbr✨ Highlights of Sunset Suite -- Catalina Suite 311br • ️ 2 bedrooms for comfort and privacybr • Private deck with tropical viewsbr • Resort pool & hot tubbr • Tennis courts + fitness centerbr • Dog-friendly (small fee)br • Free WiFi + cable TVbr • Fully equipped kitchen with modern appliancesbr • On-site parking + elevator accessbr • ✈️ Minutes to Old Town, marinas, and the airportbrbr Points of Interest Nearbybr • Smathers Beach – 1.5 milesbr • Higgs Beach – 2.5 milesbr • Southernmost Point – 3.5 milesbr • Duval Street / Old Town Key West – 3.5 milesbr • Mallory Square Sunset Celebration – 4 milesbr • Key West Butterfly & Nature Conservatory – 3 milesbr • Ernest Hemingway Home & Museum – 3.5 milesbr • Fort Zachary Taylor Historic State Park & Beach – 4 milesbr • Key West Golf Club – 3 milesbrbr ️ Shopping & Diningbr • Publix Super Market – 1.5 milesbr • Winn-Dixie Grocery – 2 milesbr • Local Boutiques & Galleries – Along Duval Street (3.5 miles)br • Key West Farmers Market (Thursdays) – 1.5 milesbr • Popular Restaurants Nearby:br • Hogfish Bar & Grill – 2 milesbr • El Siboney (authentic Cuban) – 3 milesbr • Conch Republic Seafood Co. – 4 milesbrbr Your Key West Escape AwaitsbrbrWhether you're here for laid-back beach days, world-class fishing, or the nightlife of Old Town, Sunrise Suites – Catalina Suite 311 is the perfect home base for your Key West adventure.brbr Book your stay today and experience the island lifestyle in comfort and style!brbrTHINGS TO KNOWbrUnit offers a shared, paid laundry room on site
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Exceptional(7)

$1101.38

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Private Vacation Home

Historic Old Town home with three apartments, balcony, & lighthouse view

Key West, Florida, United States

Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating history. In the 1930s, while Hemingway was living a few houses down, it was home to a popular Cuban bodega. From the 1980s through the turn of this century, potter Charles Pearson created ceramic masterpieces which are still collected today. If you keep a watchful eye, you will find some of his ceramic fish adorning buildings and homes in the neighborhood still. brbrIts current guardians have spent nearly a decade painstakingly bringing the building back to life, with Dog Tired Studio gallery up front as the proud face of the building. Julia Whitehead, the patron mermaid of the building, has been keeping an eye over this landmark since she first surfaced here in the 1800s, and she invites you to come and live like a local, just steps from Duval, in the shadow of the lighthouse.brbrMade up of three individual one-bedroom apartments, the suites are the perfect choice for several couples or families traveling together. Each of the three features a full, modern kitchen, AC splits, TV, and free WiFi. brbrAt charming Coral Cove, you'll find an updated, modern space with colorful, beachy decor and a cozy bistro table on your enclosed patio. In the upstairs Seagrass Suite, enjoy peaceful mornings with coffee on your private balcony, with a view of the Key West Lighthouse. Interior space combines modern updates with antique accent pieces, eclectic art, and cheerful pops of color. brbrFinally, at Mermaid's Retreat, you'll find a beautifully updated space, with colorful, eclectic decor and abundant natural light. Balconies off both the living room and bedroom upstairs are ideal for languid afternoons with a good book and some sweet tea. When bedtime calls, three serene sanctuaries offer a restful night's sleep. It's time to make that Key West getaway a reality at Julia Whitehead Guest Suites - all that's left to do is book. brbrTHINGS TO KNOWbrA booklet inside the apartment features the full story of Julia Whitehead Guest Suites. brThere is no parking available at this property.
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$216.06

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Private Vacation Home

Enchanting Duplex with Private Pool, Central AC, WiFi, and Private Washer/Dryer

Key West, Florida, United States

Slip into a modern duplex with distinctly bright Key West vibes! One of the two properties to rent at the Tropical Vibes house, this duplex is full of comfy details and punches of color. Not least of which is the home's star: a brilliant private saltwater pool (yes, it's heated!). You can start your vacation off right kicking back and enjoying a soak among lush tropical plants. Pull back the wide glass door for true indoor/outdoor living. You'll be able to cook out on the private gas grill and talk to guests reclining on the living room's posh couch. The open-style kitchen features a kitchen island with a separate range, perfect for preparing dinner while holding conversations. All the small appliances are next to the sink, so you'll still have plenty of space to work (or take a sip from your mixed drink). The home's comfy-yet-spacious main room includes a fan for circulation, and central air conditioning will make everyone feel comfortable throughout the home.brbrCool grey walls throughout the home (punched up with some perky Key West blue) definitely encourage a cool-and-comfortable attitude. Each bedroom features quilted linens and bright artwork that bring the cheer. You'll also find a gorgeous en suite bathroom attached to each bedroom, each featuring a beautiful standalone shower with stone accents and a glass door, a luxury sink (do you prefer stone or basin ), and a selfie-friendly LED light-up mirror. Tile work comes standard in all bathrooms, and the half bathroom shared a tile pattern with the kitchen. There's just no getting away from artistic touches in this little haven in Key West.brbrWhat's nearby:brIf you're looking to head to the beach right away, Higgs Beach is just half a mile away. The Southernmost Point of the continental United States is just over a half-mile away - take a picture and then enjoy some conch fritters at the Southernmost Beach Cafe. But if you're looking for a different kind of escape less than one mile away, take a walk through a sanctuary of colorful birds and over 50 species of butterflies at the Key West Butterfly & Nature Conservatory.brbrThings to know:brTwo twin beds can be pushed together to form a king bed, as seen in the photosbrSnowbird-friendlybrEnclosed yardbrFlat path to the front doorbrStep-free access to the bedroombrLuggage dropoff allowedbrGuests must stay for a minimum of 28 nightsbrBeach towels are available for guest usebr*Island Retreat and Island Hideaway are smaller properties within Tropical Vibes, each with their own private pool. They can be rented separately or together.brThis property is managed by Seven Keys Vacations by Casago.
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$292.77

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Private Vacation Home

Charming townhome with Old Town charm, pool access and sunset strolls

Key West, Florida, United States

Welcome to your slice of paradise in Key West's coveted Truman Annex. Tucked within the charming Shipyard community, this inviting townhome places you in the heart of it all—just steps from the sugar-white sands of Fort Zachary Taylor Beach and a short stroll to Mallory Square's legendary sunset celebrations. With Duval Street only two blocks away, you'll enjoy effortless access to world-class dining, boutique shopping, historic landmarks, and lively nightlife, all while retreating to a peaceful oasis at day's end.brbrThe Shipyard community features a beautifully renovated heated pool, perfect for leisurely afternoons in the sun. Despite its central location, the neighborhood offers a calm, residential atmosphere—an ideal balance of energy and escape that's hard to find in Old Town.brbrInside, the townhome is thoughtfully appointed for comfort and ease. Enjoy central air conditioning, WiFi, and a fully equipped kitchen with everything you need to prepare island-inspired meals. After a day of exploring, relax on your private balcony or patio, a perfect spot for morning coffee, evening cocktails, or simply soaking in the tropical breeze.brbrYou'll be moments from iconic attractions like the Ernest Hemingway Home, Key West Lighthouse, and the Southernmost Point, along with endless opportunities for snorkeling, biking, boating, and immersing yourself in the vibrant local culture.brbrWhether you're seeking adventure, relaxation, or a bit of both, this Truman Annex townhome offers an unbeatable home base for experiencing the very best of Key West living.
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Exceptional(15)

$194.19

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Condo

Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool

Key West, Florida, United States

☀️ SNOWBIRD-FRIENDLY ISLAND ESCAPE - WALK TO DUVAL, BALCONY VIEWS, POOL & BEACH ACCESS!brbrWelcome to your charming Key West hideaway, where coastal comfort, garden views, and an unbeatable location come together to create the perfect island retreat. This snowbird-friendly, two-story condo is nestled just a short stroll from the beach and blocks from some of Key West's most iconic attractions.brbr RELAX & UNWIND IN ISLAND COMFORTbr • Sip your morning coffee or evening cocktails on the furnished private balcony, overlooking lush gardens and swaying palms.br • Cool down indoors with central A/C and a comfortable living room ideal for afternoon naps or game nights.br • Enjoy meals at the dining table or head out to explore fantastic restaurants and bars just a block and a half away.br • The fully equipped galley kitchen features all the essentials, including a coffee maker for your morning pick-me-up.brbr SPACE FOR ALLbr • Two inviting bedrooms make this the perfect space for a small family or group of friends.br • The main suite includes a private en suite bath with standalone shower.br • The second bedroom has easy access to the full hallway bath.br • A stackable washer/dryer is included for added convenience during longer stays.brbr ‍♀️ COMMUNITY AMENITIESbr • Outdoor pool just steps from your doorbr • Quiet, tropical setting ideal for long stays and laid-back livingbrbr ️ PRIME LOCATION – WALK TO EVERYTHING!brbrYou're moments from Key West's top attractions:br • Fort Zachary Taylor – 0.3 mibr • Hemingway Home & Museum – 0.4 mibr • Truman Little White House – 0.4 mibr • Key West Amphitheater – 0.5 mibr • Sloppy Joe's & Duval Street – 0.6 mibr • Butterfly & Nature Conservatory – 0.8 mibr • Dry Tortugas Ferry – 1.0 mibr • Smathers Beach – 2.9 mibr • Plus, restaurants, cafes, and shops — all within 1.5 blocks!brbr WHY YOU'LL LOVE ITbr • Perfect for snowbirds seeking a sunny, long-term escapebr • Walkable to beaches, dining, and nightlifebr • Private balcony with peaceful garden viewsbr • Close to iconic attractions, yet tucked into a quiet communitybrbrCome home to the Keys. Whether you're escaping the cold or just chasing a slower pace, this charming condo offers all the essentials for a relaxing island experience.brbrTHINGS TO KNOWbrFull kitchen without a dishwasherbrStreaming services are available using your own accounts
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Exceptional(3)

$436.56

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Condo

Colorful waterfront condo with pool & hot tub, AC, W/D, & WiFi - dogs OK

Key West, Florida, United States

All the best of Key West is right at your doorstep at this colorful, second-floor condo just across the street from the gorgeous aquamarine water the Keys are known for. Smathers Beach is just down the road, and all the restaurants, bars, and cafés of Duval St. and the historic district are an easy two-mile drive or bike ride away. Onsite amenities include a pool, hot tub, sauna, and tennis court.brbrAt the condo itself, start the day on your waterfront balcony, enjoying your coffee with a side of sea breeze. The double set of patio doors lets tons of natural light inside, which features plenty of space to spread out and lots of colorful art and area rugs. The well-equipped kitchen offers a full suite of stainless steel appliances, and there's room for the whole group to eat together at the large dining room table. Head out to explore or work on your tan at the pool, returning home to relax in the central AC. Stream the latest show on the oversized sectional or use the free WiFi to upload the day's pics to social media. Step out for dinner at a local restaurant or keep it simple on one of the complex's shared grills. Call it a night in one of two comfortable bedrooms, but not before one last toast on your balcony to booking the perfect Key West escape. brbrCONDO AMENITIESbr-Outdoor poolbr-Outdoor showerbr-Hot tubbr-Cabanasbr-BBQ/Picnic areabr-Shared charcoal grillsbr-Saunabr-Tennis courtbr-Badmintonbr-Playgroundbr-ClubhousebrbrTHINGS TO KNOWbrStreaming services are available with guest accounts.brThere is an elevator in the building.
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$252.07

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Private Vacation Home

Bright Duplex with Private Heated Pool, Central AC, WiFi, & Private Washer/Dryer

Key West, Florida, United States

Enjoy a soak in your own private, heated saltwater pool at this lovely duplex! Part of the Tropical Vibes home, this duplex is a charming hideaway with plenty of room to hang out. Open the sizable glass sliding door to create a seamless indoor/outdoor space between the kitchen, living room, and pool deck. Grill up something tasty on the private gas grill, then finish it off with a glaze in the full, semi-open kitchen. There's enough room at the kitchen island to cook up the sides while something cooks on the range! Set up at the dining or the poolside table, and you can arrange a whole table with the provided flatware and glassware. When you're ready to wind down, just adjust the central air conditioning and slip into quilt bedding that reflects the bright-yet-homey vibes of Key West. Each bedroom features its own mounted TV and en suite bathroom. After all, getting ready in the morning is way more fun with a tiled standalone shower and a selfie-friendly illuminated mirror. The tile work also extends to the walls for a truly relaxing space. You'll be inspired by all the artistic touches of this home - it's only natural for the southernmost town of the continental US!brbrWhat's nearby:brIf you're looking to head straight to the beach, Higgs Beach is half a mile away! The Southernmost Point of the continental United States is just over a half-mile away - take a picture and then enjoy some conch fritters at the Southernmost Beach Cafe. Take in a bit of history at the Ernest Hemingway Home and Museum, just under one mile from the duplex. But if you're looking for a different kind of escape less than one mile away, take a walk through a sanctuary of colorful birds and over 50 species of butterflies at the Key West Butterfly & Nature Conservatory.brbrThings to know:brSnowbird-friendlybrTwo twin beds can be pushed together to form a king-sized bed as seen in the photosbrLuggage dropoff allowedbrStep-free access to the common areabrGuests must stay for a minimum of 28 nightsbrBeach towels are available for guest usebr*Island Retreat and Island Hideaway are smaller properties within Tropical Vibes, each with their own private pool. They can be rented separately or together.brThis property is managed by Seven Keys Vacations by Casago.
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Home Most popular vacation rentals in Key West