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.

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Tropical Family-Friendly Home with Private Pool Tropical family-friendly home w/private pool
Credit: Vrbo.com
Tropical family-friendly home w/private pool

Tropical Family-Friendly Home with Private Pool

Small little back yard pools are classic to many bungalows in Key West, and this listing offers one, along with an airy atmosphere, three bedrooms and three baths. A family of eight could easily call this pleasant place home for countless summer days. The ever-popular Duval Street and some of the top attractions in Key West are within walking distance, just a half-mile away.

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

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.

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

"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.

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

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.

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

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.

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Coastal Cabana Cul-de-Sac Home with Pool Coastal Cabana Cul-de-Sac Home and Pool
Credit: Airbnb.com
Coastal Cabana Cul-de-Sac Home and Pool

Coastal Cabana Cul-de-Sac Home with Pool

With bright colors, warm woods and a tiny pool surrounded by a spacious deck, this cabana epitomizes Key West home styles. Three total bedrooms, with one being up a cute staircase in a loft-like environment, create plenty of space for friends or family. This abode is also conveniently located near the center of Key West, so a slice of Blue Heaven’s “Mile High” Key Lime Pie is never out of reach.

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

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.

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Chick-A-Pea Cottage-Breathtaking Home with Pool Chick-A-Pea Cottage-Breathtaking Home with Pool
Credit: vrbo.com
Chick-A-Pea Cottage-Breathtaking Home with Pool

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.

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Dreamy Private Home and Jacuzzi Dreamy Private Home & Jacuzzi
Credit: Airbnb.com
Dreamy Private Home & Jacuzzi

Dreamy Private Home and Jacuzzi

Shabby chic in the very best way, this Airbnb is mostly polished and gleaming with modernity. Perfect for a spectacular honeymoon or just a well-deserved retreat, the spa bathrooms and Eden like outdoor space are extra special features in an already breathtaking destination. After spending nights melting away in a personal hot tub, and days traversing the historic streets, you may never want to leave.

3 Story Spacious Conch Style Home 3 Story spacious conch style home
Credit: Vrbo.com
3 Story spacious conch style home

3 Story Spacious Conch Style Home

Incredibly large and spacious, this rare find can sleep up to 10 people within its four bedrooms—three bathrooms are spread throughout the home as well. Located right within Old Town, guests have access to their own boat slip and elegantly decorated rooms. Of course, you’ve probably guessed there’s an amazing pool surrounded by towering palms. Be sure to hit up the nearby Sloppy Joes, where Ernest Hemingway used to grab a drink.

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Catamaran Yacht Sleeps 6 Catamaran Yacht Sleeps 6
Credit: Airbnb.com
Catamaran Yacht Sleeps 6

Catamaran Yacht Sleeps 6

With Key West’s overload of ocean, reefs and mangroves, one can opt to set up within a lovely catamaran. A surprising three bedrooms can accommodate six guests, and the aesthetics are more than up to date. Paddleboard right from the “front door”, or just lounge on the netting to take in the Key West beauty.

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