The Best VRBOs in Key West → 18 Picks for a Fun Holiday

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Are you going on a holiday to Key West, and you’re looking for vacation rentals where you can enjoy some privacy?

Well, you are in the right place to discover that! In order to help you save some time, I have already grouped here all options for the best VRBOs in Key West and divided them by price range, so you’ll find something for any budget here.

Whether you’re looking for a beach house with stunning sea views, a place with a prime location within walking distance to the Old Town, or a cozy holiday home with a private pool, you will find it here!

And when you do find it, remember to book it as soon as you can or at least some months in advance, so you make sure you reserve yourself a spot. These accommodations get booked out in the blink of an eye!

Ready? Let’s go!

If you are in a hurry

If you don’t have time to read the whole post, check out this quick list of the best VRBO vacation rentals in Key West:

Luxury (US$970 and up)

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William Skelton Home Heart of Key West – If you want to feel at home away from home, check out this historic house with the perfect location within walking distance to Duval Street and to the Southernmost Point Buoy of the continental USA. The house is ideal for large groups, hosting up to 12 people (9 beds), and is fully equipped with all the comforts, like a flat-screen TV, a private pool, central air conditioning, and private parking.
The Commodore’s Manor @ The Bight – This stunning 5-bedroom house with 6 beds, hosting up to 14 people, faces the water directly and is conveniently located within walking distance from the famous Higgs Beach. Here you can have your morning coffee on your private covered porch while you smell the fresh ocean breeze, chill in the living space or in your private pool, and prepare a delicious meal to treat your family on the big dining table!
Elizabeth’s Secret – Located a half block away from Duval Street in Old Town, this 3-bedroom home with 3 beds offers all the facilities you need for a holiday full of comforts. Want some examples? Here you will have access to your own private pool, a tranquil outdoor space, a dining area, and living area, and a fully equipped kitchen. Other amenities of the house include free Wi-Fi and free parking.

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Casa Amor2 Story – If you’re going to Key West on a family holiday, this three-bedroom and three-bathroom home with 6 beds is for you, hosting up to 10 guests comfortably. Here you can cook your favorite breakfast in the fully equipped kitchen and enjoy them on the big dining table, share some quality time in the living space, or splash in the large pool! This house is pet friendly, so you can even bring your four-legged friend with you!
Conch Heaven – This charming 2-bedroom home with a private heated pool is located in Old Town, within walking distance to the busy Duval Street and Mallory Square, and hosts up to 6 guests (4 beds). Here you’ll find the master bedroom on the second floor, outfitted with a king-size bed and with access to a bathroom, while the second bedroom is on the first floor and has two beds that can be easily converted to a king to meet your needs.
Villa Paradiso – This 3 bedroom (4 beds) island paradise is located in a very quiet residential area just a short stroll to Duval Street and is perfect for a weekend getaway with your loved ones, hosting up to 6 people. Here you will have access to a big shared pool, an outdoor shower, an open living area, and a chef’s kitchen decorated with light-colored walls and striking tropical tones, where you can cook your favorite meals. Doesn’t that sound great?

Mid Range (US$400 – US$800)

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Lovely Dog-Friendly Home Guest Cottage – If you’re going on holiday to Key West and you don’t want to leave your four-legged friend at home, this pet-friendly house is for you, with a fabulous location in the heart of Duval Street. The 3-bedroom cottage hosts up to 8 guests on 4 beds, so it’s perfect for a stay with your family or friends and offers access to a beautiful private pool, a spacious living area, and a ping pong table.
Atlantic Breeze – This 2-bedroom house with 4 beds is perfect if you want to be a few steps from some of the best beaches in Key West, like Smarter Beach and Higgs Beach! And when you’re not soaking up the hot sun on the white sand, you can relax in the heated pool, stay in shape in the fitness area or play in the basketball courts right nearby. And to finish your day in the best way, cook yourself your favorite dinner in the private kitchen!
Architect’s Personal Residence – This 2-bedroom beach house with 6 beds faces the ocean directly, so get ready to have breathtaking water views from your 35-foot (11 m) private balcony, from the spacious living space, or even from your own room – imagine waking up like that! If you want to spend some time outdoors, you can chill in the private pool or bubbling hot tub, have a barbecue or picnic in the outdoor areas with native tropical gardens or join cool water sports like snorkeling.

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Top Floor Ocean Views – This newly renovated house is perfectly located close to both some stunning beaches and the popular Duval Street and offers breathtaking ocean views from every window! The house offers 2 bedrooms with 4 beds for up to 6 people, as well as access to a big pool and many cool activities. Here you can go scuba diving, jet skiing, kayaking, deep-sea fishing, or playing on the 18-hole golf course nearby. Honestly, you’re just spoiled by choice!
Penthouse Level Ocean Views – Live the Dream – This charming beach house will completely blow your mind, hosting 2 bedrooms with 4 beds for up to 6 people! Here you will enjoy incredible ocean views and sunsets from your private balcony, splash in the pool (if you ever get tired of staying at the beach) and start your days with a delicious breakfast cooked in your private kitchen – perfect for making special memories with your beloved ones!
Martha Truman Suite – This one-bedroom (and 1-bed) house, located within walking distance to Duval Street, many restaurants, and the Truman waterfront park, hosts up to 3 guests, so it is ideal for both couples and solo travelers. The home is very bright, decorated with hardwood floors and vaulted ceilings, and features a big kitchen, a living area, and a private deck or patio perfect for stargazing.

Budget (up to US$350)

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Luxury High End – This completely renovated house, hosting 1 bedroom (with 2 beds) for up to 2 people, is perfect if you want to have access to luxury facilities (as can be found in the most luxurious hotels in Key West) at very reasonable prices. In fact, here, you will enjoy a chef’s kitchen fully equipped with high-end stainless steel appliances and a Keurig Coffee station, a dedicated workstation (ideal if you’re working online), a private balcony offering beautiful ocean views, a gym, and a private hot tub.
Heart of Old Town – This 2-bedroom house with 2 beds is perfect for a small family of 4 and has an amazing location in close proximity to Old Town Key West and Mallory Square, so you can explore them both whenever you want (take the 2 bikes available at the property!). But the house itself has a lot to offer, like a barbecue grill, high-speed Wi-Fi, a private pool, a fully equipped kitchen, and a spacious private back deck.
Condo in Old Town Key West’s Truman Annex – Looking for a place in Key West where to spend a romantic holiday with your special one without spending a fortune? Then stop here! This one-bedroom house (with 1 bed) is centrally located in Old Town, close to Mallory Square, and offers everything you need for a holiday full of comfort. Here you’ll have access to a pool, a fully equipped kitchen, air conditioning, free parking, and Wi-Fi.

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Simonton Studio Old Town – This 1 bedroom house with 1 bed has the perfect location to explore Key West, set in the heart of Old Town, a short walk from the Hemingway House, the Butterfly Conservatory, and Duval Street with its shops, restaurants, and museums. Here you’ll have all the tools to make your own cocktails and access to a propane grill in the courtyard to prepare some delicious shrimp. Just perfect for a romantic getaway!
Sparkling Old Town – Located within walking distance to Duval Street, this 3-bedroom house with 3 beds hosts up to 6 guests, so it is ideal for a fun getaway both with your family and friends! Here you will have access to many cool amenities, such as a big lagoon pool, bikes to explore the surrounding area, picnic tables, grills, an outdoor shower, change rooms, and a fully equipped kitchen.
Stylish Dog-Friendly Condo with Balcony – If you cannot leave without your four-legged friend, this one-bedroom house with 2 beds is for you, offering a prime location in the heart of the Key West’s Historic District and within walking distance to Duval Street. Here you will wake up to a morning coffee on your private balcony, then cook your favorite breakfast in the fully equipped kitchen or dining area.