Everyone wants something different from a Florida vacation. By visiting Key West, an island city at the southernmost point of the continental US, everyone is bound to find something they enjoy. Sun worshippers can lounge on the many beaches; history buffs will enjoy the charming Old Town and many historic sites; foodies can indulge at the many restaurants and revelers will love the city’s lively nightlife! No matter how you plan to spend your time in Key West, the city has an abundance of vacation rentals that will suit your needs. If you’ve been feeling the pull of the ocean, take a look at this list of the top 10 Vacasa vacation rentals in Key West, Florida, and turn that daydream into reality!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Sunrise Suites (from USD 350)
Sunrise Suites is a dog-friendly, two-bedroom condominium unit that features a scenic view of the salt marshes and beautifully landscaped grounds. Located in the upscale Sunrise Suites Resort, the condo is only minutes away from Key West International Airport and various shops and restaurants.
The condo itself has a private balcony that showcases the aforementioned scenic views. The kitchen is equipped with a stove, microwave, and fridge. There is also a common heated swimming pool, hot tub, and tennis court available. As for its pet policy, the condo allows only one dog weighing less than 25 lbs (11.3 kg) to be brought along.
2. Audubon House (from USD 105)
Only one block away from Duval Street, Audubon House is a single-bedroom cottage that’s only minutes away from a lot of restaurants, shops, bars, and beaches. Specifically, it’s around a mile (1.6 kilometers) away from Fort Zachary Taylor Historic State Park, Hemingway Home and Museum, and the Southernmost Point of the US.
As for the cottage, guests will find two flat-screen TVs, a stereo system, a central air conditioning system, and a pristine kitchen. The front porch invites guests to relax and enjoy the early mornings around Simonton Street. And to make all this better, the cottage is dog-friendly and allows up to four dogs weighing 30 lbs (13.6 kg) to be brought along.
3. Monroe Suite (from USD 126)
If you like going on strolls with your dog, then you can’t go wrong with Monroe Suite. This studio-style cottage is only a walking distance away from various tourist spots including the Southernmost Point, Ernest Hemingway Home and Museum, and a wide variety of restaurants.
The cottage has an on-site storage rack for you to park your bike. The kitchen is well-equipped with all the appliances you need to cook a nice meal. There is also a private patio where you can sit back and relax with a nice drink. As for the cottage’s pet policy, it allows a maximum of two dogs weighing 30 lbs (13.6 kg) or less.
4. Key Lime Calypso (from USD 209)
Key Lime Calypso is a two-bedroom cottage that promises its guests a soothing tropical-themed vacation. It features a heated swimming pool and a lush backyard garden to create a tropical aesthetic that, in the host’s own words, invites guests to “bask in the tropics of Key West”. There is also a gas grill outside to further hammer this point.
As for nearby locations, the cottage is only minutes away from various restaurants, shops, and attractions. One of the most recommended nearby places to visit is Mallory Square as guests are treated to the beautiful sunsets there daily.
5. Sunrise Suites (from USD 125)
Sunrise Suites is a cozy, dog-friendly home that showcases the gorgeous sunshine and sands of Key West. It features a balcony that offers you a wonderful view of the area. The living room and kitchen area are well-equipped and have all the amenities you’ll need for a comfortable stay. A shared swimming pool, hot tub, tennis court, and a gym are also available for guests’ leisure. Guests are only allowed to bring a single dog weighing 25 lbs (11.3 kg) or less.
As for nearby places to visit, Sunrise Suites is only minutes away from various restaurants, shops, attractions, and beaches.
6. Truman @ Duval - Studio A (from USD 124)
An unforgettable romantic getaway awaits you and your loved one at Truman @ Duval - Studio A. Located in the heart of downtown, the rental is only minutes away from many of what Key West has to offer. From the Southernmost Point of the United States to the Hemingway House, many notable attractions are only a walking distance away.
The rental itself features a snowbird-friendly theme that compliments the amenities such as a cable TV, mini-fridge, and a partial air conditioning system. Do know that pets are not allowed in this rental and that potential guests must be 25 years old or older to be able to avail of this rental.
7. Conch Casa (from USD 400)
Located in the heart of Old Town, Conch Casa is a two-bedroom rental that guarantees both convenience and comfort for its guests. The living area has a flat-screen TV, DVD player, fully-equipped kitchen, and a central air conditioning system. There is also a private hot tub for guests in the mood for a good soak.
Thanks to its convenient location, the rental is close to numerous attractions. Specifically, it’s less than a mile (1.6 kilometers) away from The Ernest Hemingway Home And Museum, The Key West Butterfly And Nature Conservatory, Hydro-Thunder Of Key West, and Truman Little White House.
8. Casa Cubana (from USD 500)
Casa Cubana is a colorful condominium unit that boasts easy access to the nearby beaches and downtown Key West. Thanks to this easy access, guests will be happy to know that they’re only minutes away from a wide variety of restaurants, shops, and attractions. This includes places like Fort Zachary Taylor Historic State Park, Smathers Beach, and Duval Square Mall.
Interior-wise, the condo sports a Mediterranean-style design that complements the various amenities like the flat-screen TV, central air conditioning system, and a kitchen area with a fridge and stove. There is also a shared community pool, gazebo, and upstairs balcony for guests to enjoy.
9. Flamingo Hideaway (from USD 111)
Nestled in the Palm Gardens condo community, Flamingo Hideaway showcases a tropical-style design that evokes island vibes for guests to enjoy. The rental comes with a cable TV, private deck, and a well-equipped kitchen. A private hot tub and shared swimming pool are also available for those in the mood for a good soak.
As for nearby places to visit, Flamingo Hideaway is only minutes away from several restaurants, shops, and attractions like Mallory Square. The rental also gives guests easy access to the beach.
10. Old Town Garden Villas (from USD 145)
Old Town Garden Villas is a dog-friendly cottage that takes pride in its prime central location and provides its guests convenient access to many places around Key West. The cottage is surrounded by numerous restaurants, historical sights, magnificent shops, and beautiful beaches.
Inside the cottage, guests will find a fully-equipped kitchen with a stove and fridge, wifi connection, and a cable TV. In terms of its pet policy, the cottage allows guests to bring a maximum of two dogs weighing 35 lbs (15.8 kg) or less.
11. Bright and airy Key West home
Located in a luxurious gated community, this vacation rental feels equal parts exclusive and homey. Up to five guests can stay in this two-bedroom home, which has everything you need to rest and relax–cooking amenities, wifi and cable, and laundry are just the beginning of the long list of perks. Though you don’t have to leave the community to enjoy yourself–they even have a pool–the location of this rental makes it ideal for sightseeing, with the quaint Old Town, stunning beaches, and museums all just minutes away.
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12. Cozy cottage with rustic charm
Overflowing with tropical vibes, you’ll feel like you’ve been transported back in time at this historic cottage! The interior is full of character, with rich wooden trim on the walls and ceilings that gives it a warm atmosphere. Outside the cottage is like a secluded oasis. It has lush tropical plants growing in the front and all around the private pool in the backyard, making it easy to block out the rest of the world!
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13. Beachy cabana with private hot tub
This cute little cottage looks small from the outside, but has plenty of room inside for up to six guests–even a dog! It’s the perfect jumping-off point for exploring the area, whether on foot to see local sights like the famous Key West lighthouse, or snorkeling and swimming at one of the area’s amazing beaches. You’ll be happy to return to this cozy home with all the amenities needed for a comfortable stay–including a dip in the hot tub to cap off the evening!
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14. Classic Key West cottage close to historic sites
Aside from its stunning beaches, Key West is also a vacation spot for history buffs. The Ernest Hemingway house, USCGC Ingham Maritime Museum, and Truman’s Little White House are all within a few blocks of each other. This charming turn-of-the-century cottage would be the perfect place for a history lover to stay. Though it feels historic, all of the amenities are modern for your convenience. There is also a front porch where you can sit and watch the world go by, and a large backyard with a covered patio and hot tub.
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15. Vacation rental in a resort environment
Enjoy all of the amenities of a resort at this lovely vacation rental! This condo is located inside the exclusive Sunrise Suites, which feels like a luxury hotel. You can play tennis, swim in the large pool, and tour around the spacious well-kept grounds. The condo is a great place to return to after a day spent out in the fresh air. It has two bedrooms and a large kitchen and living room, which open onto a private balcony perfect for watching sunsets.
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16. Tropical cottage perfect for a large group
With two bedrooms in the main cottage and a separate studio cottage on the same property, this rental is ideal for families or friend reunions! Up to eight guests can stay here comfortably. There are lots of places to gather as a group, including the stunning backyard. A covered back deck with a fan and patio furniture overlooks a refreshing built-in pool, all surrounded by flourishing tropical plants. Inside the home is just as lovely, with brightly colored decor that adds to the playful vibes.
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17. Elegant home close to everything
This stylish home would look just as appropriate in a sophisticated city as it does at the beach! The interior has crisp white decor that glows from the sun streaming in the large windows. It is located in a gated community, so you can enjoy privacy as well as access to amenities like private parking and a pool. Within walking distance is Mallory Square, a waterfront square with lots of shops, restaurants, and a daily festival at sunset to enjoy the spectacular views!
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18. Historic vacation rental with a private pool
From the second you step into this spacious vacation home, all of your worries will start to slip away! It’s easy to live on island time here, and the nostalgic, party themed decor will get you in the mood for some drinks–try to make the mojito recipe painted on the kitchen wall! The rental lends itself to letting loose and relaxing, and there is no better spot to do that than the backyard, where a covered patio sits alongside a refreshing pool.
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19. Stylish home in the center of town
You’ll be in the midst of all the action if you book this vacation rental. This lovely home is just a block away from the main street of Key West, and within walking distance to many sights like Ernest Hemingway’s house. If you’re traveling by car, there is also an off-street parking spot, but you might enjoy seeing everything more on foot. Just because you’re in the middle of town doesn’t mean sacrificing space–this three-bedroom house has plenty of room for six, and even has its own pool.
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20. Serene getaway for relaxing and exploring
Whether you’ve come to Key West for relaxation or adventures, this cute condo would be an ideal starting point for your visit! It is located right near the Old Town and within walking distance of lots of shops and restaurants. You can also take a little walk to Fort Zachary Taylor, where you can tour the fort, hike trails, and relax on the beach. Closer to home, guests at this vacation rental have access to a shared pool as well as their own private patio for sipping morning coffee, evening cocktails, or just soaking in the sunshine.
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A charming city rich with history and excitement
Much like Key West itself, each of these vacation rentals is a perfect pick whether you wish to relax or see all the sights–or a little of both! Many of them are located close to downtown, where you can either relax on a beach, learn about history, or shop and dine. They are relaxing homes away from home with all the comforts you’ll need during your down time, and the proximity to get out and explore what Key West has to offer!
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