12 Key West Vacation Rentals for the Perfect Island Getaway

Sparkling white sand beaches, stellar sunsets, scrumptious seafood, and the most delicious key lime pie in the Keys await you at the southernmost point in the United States. On land, Key West is packed with everything from fantastic restaurants and bars to artistic and historical sights. On the water, it offers everything from fishing and snorkeling to boating and jet skiing.

With all it has to offer, it’s no surprise that Key West can be expensive, and accommodations are no exception. When you spend a pretty penny, you want to make sure you get what you pay for. That’s why we walked Vrbo to find the best vacation rentals for your next trip to Key West.

Whether you want to stay in the center of the action in Old Town or are looking for a quiet getaway, we have the island retreat for you. Note that some of these options have minimum stays which are listed accordingly.

  1. Tiki Suite

  2. I had to kick off the list with this amazing tiki suite my husband and I stayed in on our last night in Key West last January. They call it a “floating house”, but it looks more like a dock that a tiki hut has been built on. We rented it because my husband wanted to stay somewhere on the water without spending a grand per night. It’s definitely on the water! Anchored in the harbor away from land, the tiki suites (there are one more) are only accessible by river shuttle.

    We relaxed in the hammock, snorkeled on the deck and enjoyed the sunset over the water. Double doors on three sides of the one-room suite also made it possible to watch the sun rise. We paddled on both stand up paddle boards until it was time to check it out.

    You must bring food, drinks and ice for the cooler as Uber Eats does not yet have a marine division. Running the air conditioner requires turning on the generator and there is only 20 gallons of water so I wouldn’t recommend it for an extended stay, but it was cool enough for one night!

    Bedrooms: 1

    Bathrooms : 1

    Sleeping: 2

    Check latest price

  3. Center Court Cottage in Downtown

  4. Center Court Cottage in Downtown

    Located one block from Duval Street, this downtown cottage is part of the Center Court Key West. The pool is shared with other guests, but you get a hot tub and deck all to yourself. Key West attractions like the Ernest Hemingway Home and Museum, the Key West Butterfly and Nature Conservatory, and the Southernmost Point are all within half a mile, so you can walk or ride a bike instead of driving or carpooling.

    Bedrooms: 1

    Bathrooms : 1

    Sleeping: 2

    Check latest price

  5. Old Town Bungalow

  6. Old Town Bungalow

    Stay close to the action at this Key West vacation rental, just half a block from Duval. This three-bedroom, two-bathroom home is within walking distance of restaurants, beaches, and attractions such as the Southernmost Point and The Key West Butterfly and Nature Conservatory. Cool off in the private lagoon-style pool out back. The only problem? There is a minimum stay of six nights.

    Bedrooms: 3

    Bathrooms : 2

    Sleeping: 6

    Minimum night: 6

    Check latest price

  7. Old Town Cottage

  8. Old Town Cottage

    Close to all the action of Old Town, this adorable one-bedroom, one-bath cottage is in a quiet residential neighborhood just a few blocks from Duval Street. Surrounded by tropical greenery, it features a professionally decorated interior and a private terrace where you can sunbathe or dine al fresco.

    Bedrooms: 1

    Bathrooms : 1

    Sleeping: 4

    Check latest price

  9. Charming Old Town Craftsman

  10. Charming Old Town Craftsman

    Located in the Old Town neighborhood on a beautiful tree-lined street south of Truman Ave, this two-bedroom, two-bathroom vacation home sleeps up to six people. People watch from the porch or enjoy the privacy of the rear outdoor living area surrounded by tropical greenery.

    Bedrooms: 2

    Bathrooms : 2

    Sleeping: 6

    Minimum night: 28

    Check latest price

  11. Composed of the old town

  12. Composed of the old town

    Are you going in a group? This over 100-year-old resort in the Old Town can sleep up to 23 people between its 10 rooms and in four separate houses on the property. The problem? There are only three and a half bathrooms. Highlights include a heated pool and hot tub, wrap-around porches on both floors of the two-story main house, and a deck. Located near the beach at Fort Zachary Taylor Historic State Park, two off-street parking spaces come with this vacation rental.

    Bedrooms: ten

    Bathrooms : 3.5

    Sleeping: 23

    Check latest price

  13. Old Town Condo

  14. Old Town Condo

    Steps from the heart of Duval Street and Truman Waterfront Park, this ground floor apartment is in a gated community of Truman Annex. This two bedroom unit has a community swimming pool, 24 hour security and parking space. A minimum stay of 28 nights is required.

    All of Key West’s top attractions including Mallory Square, Fort Zachary Taylor, Hemingway’s House and Museumthe historic seaport, and tthe southernmost point, are within walking distance.

    Bedrooms: 2

    Bathrooms : 1

    Sleeping: 4

    Minimum night: 28

    Check latest price

  15. Truman Annex Townhouse

  16. Truman Annex Townhouse

    This three-story townhouse is in the Truman Annex area of ​​Old Town. With two bedrooms and two and a half bathrooms, it can accommodate up to six people. Note that this vacation rental requires a minimum stay of seven nights.

    Mallory Square, Truman Waterfront Park, Fort Zachary Taylor, Truman’s Little White House and hotspots such as Green Parrot Bar are just steps away. It’s also less than four blocks from the action-packed 200 block of Duval Street.

    Part of the foundry building, the unit has a gated entrance and courtyard. It also comes with two bikes for tooling around the island and a designated parking spot. In addition, the complex has a swimming pool which is just across the street.

    Bedrooms: 2

    Bathrooms : 2.5

    Sleeping: 6

    Minimum night: 7

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  17. Truman Annex House

  18. Truman Annex House

    Also located in the gated community of the Truman Annex, this lovely two-bedroom, two-and-a-half-bath vacation home requires a minimum stay of seven nights. The master bedroom has a private terrace that overlooks the beautiful outdoor space. Surrounded by lush tropical landscaping, the deck features both a covered seating area and a picnic table.

    A parking space is provided out front, but all the action of the old town, including restaurants, shops, water sports and nightlife, is close by. It’s also a few steps from the communal pool!

    Bedrooms: 3

    Bathrooms : 3

    Sleeping: 8

    Check latest price

  19. Beachfront home in Raccoon Key

  20. Beachfront home in Raccoon Key

    Those who want to avoid the crowds should check this out beachfront property in Raccoon key. Up to eight people can stay in its four bedrooms. There’s no pool, but there is a ladder on the seawall so guests can swim or kayak in the canal. You can even bring your own boat and/or well-behaved pet.

    Soak up the sun on the beautifully landscaped courtyard, dotted with palm trees. Choose fresh limes from the key lime tree. Beaches, restaurants and the Key West Golf Club are all nearby.

    Bedrooms: 4

    Bathrooms : 3

    Sleeping: 8

    Minimum night: 28

    Check latest price

  21. Stock Island Sanctuary

  22. Stock Island Sanctuary

    A little further out on Stock Island, this peaceful retreat requires a minimum stay of 30 nights. Located off the 17th fairway in a gated golf course community, this spacious home offers a quiet oasis for up to six people and two dogs.

    Highlights include a pool with an oversized deck, porch and deck, lush tropical landscaping, and golf course lake views from the den. Watch the sunrise from the upper back balcony or lower porch.

    Duval Street, the beaches and Conch Harbor are a short drive away. 24 hour security and two off-street parking spaces are provided. If this Stock Island vacation is booked on the dates you want, check out this other two bedroom townhouse at a golf resort.

    Bedrooms: 3

    Bathrooms : 2.5

    Sleeping: 6

    Minimum night: 30

    Check latest price

  23. Galleon Resort Waterfront Condo

  24. Galleon Resort Waterfront Condo

    Located near Mallory Square in Key West’s historic Seaport District, this two-bedroom suite sleeps up to six people. Note the seven-night minimum stay with Saturday check-in only. Bring a boat? The marina at the Galleon Resort offers mooring space for boats and yachts up to 140 feet.

    Overlooking the Gulf of Mexico in historic Old Town, this resort features a tiki bar, waterfront pool, private beach, observation deck offering 360 degree panoramic views of Key West, on-site dining room, exercise room and sauna.

    Just two blocks from Duval Street, the resort is within walking distance of attractions, art galleries, shops, and restaurants. Fishing charters, sunset cruises, parasailing, snorkeling, dolphin watching, glass bottom boats, and jet ski and scooter rentals are all available at the marina or near.

    Bedrooms: 2

    Bathrooms : 2

    Sleeping: 6

    Minimum night: 7

    Check latest price

Related reading:

  1. How to get around Key West
  2. How to Spend a Day in Port Key West
  3. 12 Incredible Outdoor Experiences from Key Largo to Key West

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