Key West vacation rentals

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Top-rated houseboats for rent in Key West

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost
Houseboat in Key West
The simple life on Seaplicity!
Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Also, you can cook your own meal in the fully equipped galley! Shuttle service takes you to old town Key West! Ask about adding a Captained Sailing Adventure to your trip!
Nov 27 – Dec 4
$251 per night
4.67 out of 5 average rating, 3 reviews
Guest favorite
Houseboat in Islamorada
360 Degree Waterview Houseboat II, Florida Keys.
PLEASE READ Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada, 2 days minimum. Do not arrive after dark NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of clothes.
Nov 30 – Dec 7
$162 per night
5.0 out of 5 average rating, 7 reviews
Guest favorite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
You’ll treasure your time at this memorable place. Located in beautiful Islamorada. If you want a memorable trip with that laid back attitude then look no further. This 2 bedroom 1 bath floating home has everything you need. Enjoy your morning coffee on the deck and in the evening enjoy that adult beverage as you watch nature and sunsets. All of our Villas are unique in their own way, The Hemingway is decorated in a theme that highlights the influence Ernest Hemingway had on the Florida Keys.
Dec 15 – 22
$269 per night
4.92 out of 5 average rating, 13 reviews

Stay near Key West's top sights

Duval Street62 locals recommend
Mallory Square100 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend
Sebago Watersports6 locals recommend

Key West houseboats

Houseboat in Marathon
Houseboat Heaven -Private Island
Apr 19 – 26
$446 per night
New place to stay
Houseboat in Stock Island
Stella on Stock Island
Apr 8 – 15
$350 per night
New place to stay
Houseboat in Marathon
Farándula at Sea House
Feb 14 – 21
$193 per night
4.1 out of 5 average rating, 10 reviews
Superhost
Houseboat in Key West
Key West Houseboat Paradise
Jun 1 – 8
$333 per night
4.8 out of 5 average rating, 247 reviews
Guest favorite
Houseboat in Islamorada
Getaway to Blackbeard's Hideout
Sep 12 – 19
$269 per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Houseboat in Stock Island
Great View in a private marina!
Apr 16 – 23
$585 per night
4.86 out of 5 average rating, 21 reviews
Superhost
Houseboat in Islamorada
HOUSEBOAT 2BD,1.5 BA,PRIVATE KEYS COTTAGE LIONFISH
Dec 28 – Jan 4
$254 per night
4.73 out of 5 average rating, 122 reviews
Guest favorite
Houseboat in Islamorada
Aqua Lodge in the Florida Keys!
Oct 3 – 10
$269 per night
4.83 out of 5 average rating, 6 reviews
Superhost
Houseboat in Stock Island
Charming Houseboat in Key West
Jun 17 – 24
$247 per night
New place to stay
Superhost
Houseboat in Stock Island
Great view in private Marina ! No regrets
Jan 9 – 16
$699 per night
New place to stay
Guest favorite
Houseboat in Big Pine Key
1 Bedroom Aqualodge # 6 Tarpon
Jan 12 – 19
$286 per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Houseboat in Big Pine Key
2 Bed Aqualodge # 13 Barracuda
Dec 26 – Jan 2
$296 per night
4.8 out of 5 average rating, 25 reviews

Key West houses

Guest favorite
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Dec 13 – 20
$444 per night
4.94 out of 5 average rating, 267 reviews
Superhost
Home in Key West
Rooftop Penthouse - Luxury Penthouse in prime Down
Jul 7 – 14
$679 per night
4.85 out of 5 average rating, 108 reviews
Guest favorite
Home in Marathon
Oceanfront Tiny Villa in the Heart of the FL Keys
Aug 7 – 14
$430 per night
4.96 out of 5 average rating, 118 reviews
Guest favorite
Home in Key Largo
Your Keys Getaway!
Jan 26 – Feb 2
$152 per night
4.9 out of 5 average rating, 344 reviews
Guest favorite
Home in Cudjoe Key
Newly Renovated Oceanside House with Pool
Nov 28 – Dec 5
$354 per night
4.89 out of 5 average rating, 182 reviews
Guest favorite
Home in Marathon
Beachfront Villa - Florida Keys
Oct 8 – 15
$350 per night
4.9 out of 5 average rating, 154 reviews
Guest favorite
Home in Marathon
Marathon one-level home on the Marina - with slip!
Jun 2 – 9
$502 per night
4.97 out of 5 average rating, 116 reviews
Guest favorite
Home in Cudjoe Key
Sunrise Beach Escape
Nov 25 – Dec 2
$350 per night
4.91 out of 5 average rating, 101 reviews
Guest favorite
Home in Cudjoe Key
Cudjoe Key Home with a View
Aug 28 – Sep 4
$323 per night
4.96 out of 5 average rating, 114 reviews
Superhost
Home in Key West
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute
Aug 27 – Sep 3
$507 per night
4.85 out of 5 average rating, 135 reviews
Guest favorite
Home in Marathon
Sea Ray Cove , 75’ boat dock, 1 block from beach!
Nov 5 – 12
$525 per night
4.99 out of 5 average rating, 103 reviews
Superhost
Home in Key Colony Beach
Waterview from three sides, Cabana Club, 30' Docks
Jan 20 – 27
$339 per night
4.82 out of 5 average rating, 129 reviews

Key West condos

Superhost
Condo in Key West
Beach Club Ocean Front 2BR Condo
Dec 20 – 27
$835 per night
4.93 out of 5 average rating, 132 reviews
Guest favorite
Condo in Key West
A Perfect Getaway
Jun 30 – Jul 7
$393 per night
4.85 out of 5 average rating, 122 reviews
Guest favorite
Condo in Key Colony Beach
Oceanfront Breeze, Stunning Views, Beach/Pool
Dec 28 – Jan 4
$475 per night
4.92 out of 5 average rating, 190 reviews
Guest favorite
Condo in Key West
Large waterfront 2/2 end unit with boat slip
Jan 21 – 28
$620 per night
4.88 out of 5 average rating, 137 reviews
Guest favorite
Condo in Key West
La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Sep 24 – Oct 1
$256 per night
4.83 out of 5 average rating, 235 reviews
Guest favorite
Condo in Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 14 – 21
$203 per night
4.92 out of 5 average rating, 110 reviews
Guest favorite
Condo in Marathon
Sombrero Beach Tropical Getaway
Jul 25 – Aug 1
$201 per night
4.87 out of 5 average rating, 185 reviews
Superhost
Condo in Tavernier
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Dec 10 – 17
$233 per night
4.88 out of 5 average rating, 220 reviews
Guest favorite
Condo in Tavernier
Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Aug 10 – 17
$268 per night
4.95 out of 5 average rating, 103 reviews
Guest favorite
Condo in Tavernier
Sea View Oceanfront Condo
Feb 6 – 13
$267 per night
4.97 out of 5 average rating, 219 reviews
Guest favorite
Condo in Tavernier
Best View Ocean Pointe Pool Beach King Bed, Gated
Jul 27 – Aug 3
$363 per night
4.95 out of 5 average rating, 153 reviews
Guest favorite
Condo in Key Largo
KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!
Aug 7 – 14
$488 per night
4.97 out of 5 average rating, 145 reviews

Quick stats about vacation rentals in Key West

Total rentals

1.8K properties

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

490 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

52K reviews

Nightly prices starting at

$10 before taxes and fees

Your guide to Key West

All About Key West

Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.

Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.


The best time to stay in a vacation rental in Key West

Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.


Top things to do in Key West

Snorkeling

Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.

Ghost tours

Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.

Key lime pie

Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.

Frequently Asked Questions

  • How is the weather in Key West?

    Key West has a tropical climate with warm temperatures year-round. Summers, from June to August, can be hot and humid, often reaching 90°F (32°C). Winters, from December to February, are milder, with temperatures typically around 70°F (21°C), and less rainfall.

  • What are some of the best things to do in Key West?

    Popular activities in Key West include exploring the vibrant coral reefs on a snorkeling trip, discovering local marine life at the Key West Aquarium, or visiting the historic Fort Zachary Taylor State Park. A stroll along Duval Street for shopping and local cuisine is also recommended.

  • What is the best time of year to visit Key West?

    Key West is particularly lively between March and May, with milder temperatures and fewer crowds. During these months, you can enjoy events like the Conch Republic Independence Festival and the Key West Songwriters Festival.

  • What are the best places to stay in Key West?

    Some highly-rated areas to stay in Key West include Old Town, a historic district with classic architecture, Truman Annex for its peaceful atmosphere, and New Town for its modern conveniences. Duval Street is also favored for its proximity to dining and shopping options.

  • What are the best places to visit in Key West?

    Key West is known for diverse attractions such as the Ernest Hemingway Home and Museum, where the renowned author once lived, and the Key West Butterfly and Nature Conservatory. Don't miss the stunning sunsets at Mallory Square, and the view from the historic Key West Lighthouse. The Southernmost Point Buoy is also frequently visited.

  • What are some hiking trails in Key West?

    While Key West is not known for its hiking, you can enjoy a leisurely walk at the Key West Tropical Forest and Botanical Garden. The Island City National Historic District also has interesting paths through the town's picturesque streets.

  • What are some family activities to do in Key West?

    Families can enjoy a visit to the Key West Shipwreck Museum, engage with interactive exhibits at the Florida Keys Eco-Discovery Center, or have fun exploring the Key West Aquarium. A ride on the charming Conch Tour Train is also a delightful way to see the city.

  • What are some of the best day trip ideas in Key West?

    For a memorable day trip, explore the natural beauty of Dry Tortugas National Park, which is accessible by ferry or seaplane. Also, consider a wildlife expedition at the Key West Wildlife Center, or learn more about the region's history with a visit to Fort East Martello Museum.

  • What types of vacation rentals are available in Key West?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Key West. From over 520 house rentals, over 10 houseboat rentals to over 410 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Key West?

    Yes! Work meets play with ease at over 910 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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