63 Properties in Key West, Florida, United States of America. ${startDate} through ${endDate}

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Fantasy Fest Street FairDuval Street Oct 23-25

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Ernest Hemingway Home and Museum

Southernmost Point

Mallory Square

Key West Shipwreck Museum

Key West Butterfly and Nature Conservatory

Duval Street

Fort Zachary Taylor Historic State Park

Florida Keys Eco - Discovery Center

Smathers Beach

Dry Tortugas National Park

Florida Keys National Marine Sanctuary

Clarence S. Higgs Memorial Beach Park

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Truman Beach

Boca Chica Nude Beach

Key West Tropical Forest and Botanical Garden

Sails To Rails Museum at Flagler Station

Fort Jefferson

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Key West

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eviivo NORAM

RC - EOS Hospitality, LLC

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63 properties available in your date range

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A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

Balcony

Beach

Hot tub on site

Balcony, Beach, Hot tub on site

Fully refundable

9.49.4 out of 10

Exceptionalexceptional

1,318 reviews(1,318 reviews)

$199 nightly

The current price is $269 total

$269 total

Total with taxes and fees

We have 5 left at this price

Mon, Oct 26 - Tue, Oct 27

Mon 26 of October 2026 to Tue 27 of October 2026

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A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

VIP Access

The Perry Hotel & Marina Key West

Stock Island

Balcony/patio

Bar and lounge

2 restaurants

Balcony/patio, Bar and lounge, 2 restaurants

Fully refundable

9.49.4 out of 10

Exceptionalexceptional

1,316 reviews(1,316 reviews)

$31 off

$157 nightly

The current price is $239 total

$239 total

Total with taxes and fees

Tue, Oct 27 - Wed, Oct 28

Tue 27 of October 2026 to Wed 28 of October 2026

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A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

A swimming pool surrounded by palm trees and a natural rock formation.

VIP Access

Havana Cabana at Key West

New Town

Hot tub on site

Bar and lounge

Restaurant

Hot tub on site, Bar and lounge, Restaurant

9.09.0 out of 10

Wonderfulwonderful

1,880 reviews(1,880 reviews)

$149 nightly

The current price is $231 total

$231 total

Total with taxes and fees

Tue, Oct 13 - Wed, Oct 14

Tue 13 of October 2026 to Wed 14 of October 2026

More information about Havana Cabana at Key West , opens in a new tab

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Photo gallery for Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

Photo gallery for The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

Photo gallery for Havana Cabana at Key West

Havana Cabana at Key West