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Key West Vacation Rentals

Compare 2,272 available properties from 23 providers

Key West

Save up to 45%

Best Vacation Home Deals in Key West

-34%

e.g. 8/31 - 9/7

House ∙ 8 guests ∙ 3 bedrooms

Key West, Florida Keys, Florida, United States

from $986 ~~$1,501~~

RedAwning

4.8

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-45%

e.g. 12/1 - 12/8

House ∙ 10 guests ∙ 4 bedrooms

Key West, Florida Keys, Florida, United States

from $1,115 ~~$2,015~~

RedAwning

4.9

View deal

-41%

e.g. 12/1 - 12/8

House ∙ 10 guests ∙ 4 bedrooms

Key West, Florida Keys, Florida, United States

from $1,115 ~~$1,905~~

RedAwning

4.7

View deal

Find a vacation home that fits your preferences among the 2,272 fantastic accommodations from 23 providers in Key West. By directly analyzing these properties, HomeToGo brings you the best deals as well as the highest rated vacation homes in Key West.

Recommended Vacation Rentals in Key West

Rent a vacation accommodation in Key West: from $72 per night

House ∙ 2 guests ∙ 1 bedroom

Key West, Florida Keys, Florida, United States

from $102

VRBO

4.0

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House ∙ 2 guests ∙ 1 bedroom

Key West, Florida Keys, Florida, United States

from $404

VRBO

4.6

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Apartment ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $89

VRBO

4.8

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House ∙ 2 guests ∙ 1 bedroom

Key West, Florida Keys, Florida, United States

from $402

VRBO

4.8

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House ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $562

VRBO

4.4

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Apartment ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $481

VRBO

4.9

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Apartment ∙ 3 guests ∙ 1 bedroom

Key West, Florida Keys, Florida, United States

from $343

VRBO

5.0

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Apartment ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $140

VRBO

4.4

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Apartment ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $512

VRBO

4.8

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Vacation Houses With Pools

Pool

House ∙ 2 guests

Key West, Florida Keys, Florida, United States

from $400

VRBO

4.5

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Pool

Apartment ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $200

VRBO

4.8

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Pool

House ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $703

VRBO

4.6

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Apartments With Balconies or Patios

Balcony/Patio

Apartment ∙ 2 guests

Key West, Florida Keys, Florida, United States

from $199

VRBO

4.7

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Balcony/Patio

Apartment ∙ 4 guests ∙ 2 bedrooms

Key West, Florida Keys, Florida, United States

from $621

VRBO

4.6

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Balcony/Patio

House ∙ 3 guests ∙ 1 bedroom

Key West, Florida Keys, Florida, United States

from $283

VRBO

4.9

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Vacation Homes With Fishing Spots Nearby

Fishing

Apartment ∙ 2 guests

Key West, Florida Keys, Florida, United States

from $131

VRBO

4.4

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Fishing

Apartment ∙ 2 guests

Key West, Florida Keys, Florida, United States

from $236

VRBO

4.8

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Fishing

House ∙ 2 guests ∙ 1 bedroom

Key West, Florida Keys, Florida, United States

from $480

VRBO

4.9

View deal

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Popular Rental Amenities in Key West

Kitchen (1,498)
AC (1,427)
TV (1,426)
Internet (1,381)
No smoking (1,354)
Microwave (1,294)
Parking (1,177)
Washer (1,088)
Dishwasher (929)
Pool (922)
Balcony/Patio (857)
Grill (719)

Accommodations can be chosen based on different criteria. Above, you can see the number of properties that provide a specific feature in Key West. In Key West, 1,646 rentals offer "TVs". So, if you never miss an episode of your favorite show, select the TVs filter to compare these properties. Plan your vacation in advance if you like to end your days curled up by the fire or you love sweating the stress away in saunas. There are just 6 listed rentals providing "fireplaces" and 79 properties with "saunas."

Price and Availability Index in Key West

Vacation Rental Price Information in Key West

This graph displays the average prices for the next twelve months in Key West. Prices reach their highest point in February, where prices are an average of $601 a night (2/9 - 2/16). Prices decrease in August to an average of $274 per night (8/24 - 8/31).

Rental Availability Information in Key West

Our availability graph helps you identify the busiest months in Key West. So far, the week with the least available rentals in Key West is in December (12/22 - 12/29). It will be easy to find a rental that suits you in a week of July (7/27 - 8/3), as 82% of the rentals are still available.

The Weather in Key West

Max. Min. 79° 72° 7 days 7	Max. Min. 77° 68° 6 days 6	Max. Min. 79° 70° 7 days 7	Max. Min. 82° 75° 6 days 6	Max. Min. 86° 77° 8 days 8	Max. Min. 88° 79° 12 days 12	Max. Min. 90° 81° 12 days 12	Max. Min. 90° 81° 17 days 17	Max. Min. 88° 79° 17 days 17	Max. Min. 84° 77° 11 days 11	Max. Min. 81° 72° 8 days 8	Max. Min. 79° 72° 9 days 9
Jan.	Feb.	Mar.	Apr.	May	June	July	Aug.	Sep.	Oct.	Nov.	Dec.

- Rainy days

Above are the weather conditions for Key West. July is the warmest month in Key West with average maximum temperatures of 89°. On the contrary, the coolest month is February. The rainiest month is July while the driest month is February.

Accommodations in Key West

More than half of the accommodations (51.92%) in Key West are house rentals. They are the most prevalent vacation properties there. In addition, these properties have an average size of 1,310 ft² and a median price of $611 per night. Moreover, this type of lodging is great for medium-sized groups and families, as the majority of house rentals can welcome 6 guests. If you are interested in another accommodation type, you could consider apartment rentals, which are the second most common accommodation type in Key West. Our data reveals that the average price of apartment rentals is $424 per night for an area of 970 ft².

Choose a Key West Vacation Rental for an Unforgettable Beach Vacation

Key West is the place to go if you're looking for fantastic diving and snorkeling whilst maintaining all the benefits of a city break. It is ideal for any type of stay, from a weekend getaway to a longer vacation. Relish a quiet seaside break and soak up the Caribbean vibes by staying in a Key West vacation rental. Key West has it all, from tranquil seaside nooks to lively entertainment.

Show all 2,272 properties

Getting There

Reaching Key West

There are several ways to get to your Key West vacation rental: by air, land, and sea. Delta Airlines, American, United, and Silver Airways have flights to Key West International Airport. If you are driving, take the Florida Turnpike south from Miami to Key West. A high-speed ferry also operates daily, sailing from Fort Myers Beach and Marco Island. Alternatively, Greyhound buses will take you to Key West from Miami International Airport.

Food & Drinks

Dining in Key West

Cuisine in Key West is a tantalizing mix of Bahamian, Cuban, and New England influences, drawing on the best the sea has to offer. Key West is known affectionately as the "Conch Republic." This mollusk is served in salads, chowders, and as part of main courses.

Do not leave any restaurant without sampling the famous Key lime pie, a sinful concoction of condensed milk and Key limes perched on a Graham cracker crust and topped with decadent whipped cream.

Weather & Climate

Sunshine Year Round

Key West is a year-round travel destination, as it is blessed with a tropical climate similar to the Caribbean. The coolest month is January and the hottest is July. The island has two main seasons: wet (May to October) and dry (November to April).

Attractions

History and More

Apart from diving, swimming, snorkeling, and water-based activities, there is plenty to see on land. Visit the attractive Old Town with its pastel-hued, conch-style houses, and don't forget to check out the Fort Zachary Taylor. The latter is a historic state park that is now used as a venue for events such as Civil War reenactments.

Stop at Mallory Square, a plaza known for its "Sunset Celebration." People gather here to view arts and crafts, eat from food carts, enjoy street performances, and watch the remarkable sunset. The New Town, which is on the east side of the island, features malls, shopping centers, schools, and residential zones.

Another famous attraction in Key West is the replica of a buoy made from concrete located at South and Whitehead Streets, which marks the "southernmost point" of the Continental USA.

Art & Culture

Key West Culture

When it comes to culture and history, Key West has so much to offer. Explore the Audubon House and Tropical Gardens, a museum dedicated to the American painter, naturalist, and ornithologist John James Audubon.

Another must-visit for art enthusiasts is the Studios of the Key West, a community for artists which comprises work spaces, an exhibition hall, sculpture garden, and houses and cottages. An excellent program of performances, talks, and concerts is sure to cater to all tastes and interests.

In addition, be sure to check in advance if there are performances by the Key West Contemporary Dance Company, based at the Waterfront Playhouse. The Tennessee Williams Theater is another cultural hotspot, with a program packed with dance, theater, and musical performances.

Family Activities

Traveling with Children

Traveling with kids? Key West has something for everyone, young and old. Visit Key West Nature Preserve Park, where you can enjoy walks and hikes through a lush mangrove forest.

The Key West Marine Park is great for swimming and snorkeling, and is protected by buoys, making it safe for younger adventurers. Astro City is a popular playground located across from Higgs Beach, while Florida Keys Eco-Discovery Center features interactive displays about reefs and mangroves.

Local conveniences

Self-catering in your Key West vacation rental

One of the best ways to experience the island is to stay in a Key West vacation rental. You will have lots of room if you are traveling with family or friends, as well as complete privacy. What's more, you can enjoy that home-away-from-home feeling and unwind after a long day of exciting activities.

Most Key West vacation rentals also come with a fully fitted kitchen, allowing you the flexibility to cook at home when it suits you.

Sights & things to do in Key West

Uncover Key West Island gems

Fort Zachary Taylor Historic State Park

Known simply as Fort Taylor or Fort Zach, this park is centred around a Civil War-era fort. Visitors can enjoy cycling, swimming, snorkeling and fishing here. Grab a bite at the open-air Cayo Hueso Café.

Harry S. Truman Little White House

The winter White House for former president Harry S. Truman is a great place to learn about Key West's history. Local guides add color to the experience with their anecdotes.

The Ernest Hemingway Home and Museum

Learn about the literary icon's numerous romantic relationships, friendships and writings through a guided tour of his erstwhile residence.

Dry Tortugas National Park

Seventy miles from Key West, this secluded park is home to Fort Jefferson, wild birds, coral reefs and marine life. It's the ideal location for a camping excursion.