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Top 14 Key West Vacation Rentals

Key West is a mixture of history and island life, with outdoor adventures and exciting nightlife on offer. Many swoon-worthy hotels dot the shores of the southernmost Florida Key, but authentic cottages that have been renovated to have both historic charm and modern features, along with other unique rentals, reside here. Renting through Vrbo or Airbnb can often provide couples, families and groups with more creature comforts and space to spread out, and sometimes can be a less expensive option for longer stays. So get ready for the real Key West treatment and take a look at the best rentals available.

Quaint Cottage By Duval LA CASITA EN CIMA  OLD TOWN Quaint Cottage By Duval
Credit: LA CASITA EN CIMA OLD TOWN Quaint Cottage By Duval by Airbnb.com

Quaint Cottage By Duval

Sleekly classic on the inside, the home opens up to a glorious deck and modern pool, in the backyard oasis. You’ll notice many true Key West features within the overall polished, updated cottage. Located on Angela Street, which is within Historic downtown, guests can easily walk or bike to other famous streets, and attractions like Ernest Hemingway’s home, which is a family-friendly museum.

Chick-A-Pea Cottage-Breathtaking Home with Pool Chick-A-Pea Cottage-Breathtaking Home with Pool
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Chick-A-Pea Cottage-Breathtaking Home with Pool

With its own backyard cabana and pool with waterfall, this quaint cottage with interior shiplap and wood floors is a renovated gem with all the up to date features of a high-end home. While you’ll be resting your head in style inside, you’ll likely end up recreating outside by the grill and lounging nooks—the pool is even heated for all-season enjoyment.

Bella Vita Condo Bella Vita, 1 Bedroom Condo Steps From Duval – Key West
Credit: Bella Vita, 1 Bedroom Condo Steps From Duval – Key West by airbnb.com

Bella Vita Condo

Also available on Airbnb is this one-bedroom, one-bathroom condo for two people. One of the coolest Airbnbs in the Florida Keys, it’s less than a half block from Duval Street and in Old Town. The home has a galley kitchen, living room with leather sofa, king-size bed, desk area, Wi-Fi, and two smart TVs. When you stay here, you can walk to many Key West attractions, such as bike and scooter rentals. On-street parking is available here for guests. Overall, this is a great choice for two adults looking to experience the best of Key West.

Historic Cigar House A highly requested unit in a unique hotel
Credit: A highly requested unit in a unique hotel by Airbnb.com

Historic Cigar House

The historic Cigar House is part of the Island City House Hotel, and this Airbnb rental is Unit #12 inside of it on the third floor. It’s one of the most popular units in the building and has a private balcony that overlooks the pool. You’ll be just three blocks from Duval Street, which means it is quiet for sleeping but still close enough to get out and do things. This Airbnb accommodates four guests and has a queen-size bed in the bedroom, a sofa bed in the living room, kitchen, and access to all the hotel amenities. There is no elevator in the building, so you’ll need to climb stairs to access the unit.

Breezy Florida Home Shared pool space
Credit: Shared pool space by Airbnb.com

Breezy Florida Home

Whitewashed wood walls and cheerful hues give this bungalow a ship-like design. The shower is adorned with a beautiful aqua tile, which is consistent with the overall coastal theme. A lovely, canvas shaded pool is shared with the neighbors but remains an overall quiet place to soak in this Florida Key. There’s a 28-night minimum, but it will be easy to make this your new home away from home with its easy access to Old Town dotted with restaurants and shops as well as Higgs Beach, just a few blocks south.

Sun, Sea, and Sky in the Truman Annex A lovely space in a walkable area
Credit: A lovely space in a walkable area by Vrbo.com

Sun, Sea, and Sky in the Truman Annex

Available to rent on Vrbo, this condo is just two blocks from Duval Street in the heart of Old Town and sleeps four people. The host considers pets if you stay for at least 28 days. Known as Sun, Sea & Sky, the condo has a large rear deck, private art, mirrored walls, and access to a pool. Other features are a washer and dryer, central A/C, off-street parking, linens, and towels. Fort Zachary Taylor State Park and the beach are just a quarter-mile away. The condo is part of the Shipyard Condominiums complex in the gated Truman Annex community.

Luxury High-End Condo Luxury High-End Condo
Credit: Luxury High-End Condo by Vrbo.com

Luxury High-End Condo

For your trip to Key West, it’s fun to stay in a luxury condo with all the comforts of home, such as this one that is available on Vrbo. It is a 1,100-square-foot condo that sleeps four people and has one bedroom and one bathroom. The kitchen has high-end, stainless steel appliances, while the interior also has a dedicated work area and high-speed internet. There are two bikes that you can use here, as well as comfy chairs on the balcony, smart TV, and coastal décor. Guests will also have access to the condo complex’s tennis courts, gym, pool, hot tub, sauna, picnic area, and private natural beach area.

"RIPTIDES" Stylish Studio Located in a Central Location
Credit: "RIPTIDES"~Stylish Studio Located in a Central Location Near All the Action by Vrbo.com

"RIPTIDES" Stylish Studio Located in a Central Location

Nautically decorated, this studio apartment with a cuddly bed and bath is all you need, especially when located so optimally within the city. Just one block from Duval Street and its top restaurants and significant sites, as well as a butterfly conservatory, are some of the exciting things to do. Nightlife also cranks up after dark and offers a fun, quirky atmosphere for the real partiers, or even just for the observers.

The Tiki Suite

The Tiki Suite

One of the coolest ways to experience Key West is to stay in this Tiki Suite, which is a floating structure for two people. It is one of the most unique vacation rentals in Florida, anchored in the harbor and only accessible by boat. There is a local marine service company that provides water shuttle service here. Book this Airbnb for an off-grid living experience that gives you a sense of boat life but has some of the modern conveniences of glamping. The host provides you with a hammock, snorkel gear, and stand-up paddleboards. The interior has a king-size bed, air conditioning to be used sparingly, Wi-Fi through a jetpack, and limited fresh water. You’ll need to bring your own food, drinks, and toiletries. There is an electric macerating toilet and a shower with a water heater for guests to use on the structure.

Casa Loca- One of a Kind Estate Casa Loca- One of a kind estate
Credit: Casa Loca- One of a kind estate by Vrbo.com

Casa Loca- One of a Kind Estate

This home feels like a mini-mansion with its glimmering appeal and upscale aesthetics. Three bedrooms and two bathrooms provide ample space, along with the galley kitchen and an abundance of lounging space. The outdoor landscape is colorful and tropical from the moment one approaches the cottage, and out back is a refined pool space that belongs in a movie—it’s small like most Key West home pools, but elegantly presented and a centerpiece to the space.

Catherine House: A charming Old Town Key West Cottage Catherine House: A charming Old Town Key West cottage
Credit: Catherine House: A charming Old Town Key West cottage by Vrbo.com

Catherine House: A charming Old Town Key West Cottage

From the sunken in porch perfect for breezy days, deep wooden accents to the colorfully tiled kitchen, this dwelling exudes copious amounts of local charm. The decor is traditional, with just the right amount of island flair, and four people can comfortably enjoy this little piece of Key West heaven. The super-slim pool fits perfectly in the small backyard, complete with a bistro table for enjoying snacks or breakfast.

Stunning Townhouse with Full Kitchen A rare find for resort living
Credit: A rare find for resort living by Airbnb.com

Stunning Townhouse with Full Kitchen

Another fun way to experience Key West is to rent this two-bedroom, 2.5-bathroom townhouse that is in the Santa Maria resort. It is a condo that overlooks a pool and sleeps six people. With this rental, you’ll be just two blocks from the beach and two blocks from Duval Street too. It also has two balconies with outdoor furniture and a full kitchen. You don’t have to pay a resort fee to stay here, but you will need to pay extra if you want a daily cleaning service.

Old Town Private Room That Opens to Pool and Garden Old Town Private Room That Opens to Pool and Garden
Credit: Old Town Private Room That Opens to Pool and Garden by airbnb.com

Old Town Private Room That Opens to Pool and Garden

It is also possible to rent a private room in a Key West home and enjoy a location in the heart of Old Town. It’s a quiet and secluded room with its own private entrance, a double bed, and a modern bathroom. Guests can use the host’s pool and fenced-in yard too. For your convenience, the host provides guests with beach towels, a coffeemaker, a small refrigerator, and Wi-Fi access.

43' Luxury Fishing Yacht in Friendly Marina 43' Luxury fishing yacht in friendly marina
Credit: 43' Luxury fishing yacht in friendly marina by Airbnb.com

43' Luxury Fishing Yacht in Friendly Marina

Adorned with sleek interior wood from the cabinets to the floors, and a spacious sun deck, folks can live the yacht life. It’s surprising to find four bedrooms and two baths in the sea voyager—kids will especially enjoy the snug bunk beds. Staying fastened to the dock, guests can’t take the boat for a joy ride but can also contact the host about fishing trips. Hop right off onto the dock only to be greeted by restaurants like the Hogfish Bar and Grill.

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