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

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Fantasy Fest Street FairDuval Street Oct 23-25

Southernmost Half Marathon & 10K Run Key WestFlorida Keys Beaches Oct 11-12

Chart Room Daily Hangout HeadquartersFlorida Keys Beaches Sep 3-4

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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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Boca Chica Nude Beach

Key West Tropical Forest and Botanical Garden

Sails To Rails Museum at Flagler Station

Fort Jefferson

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eviivo NORAM

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RC - EOS Hospitality, LLC

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55 properties available in your date range

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A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

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

Pool
Hot tub

9.49.4 out of 10

Exceptionalexceptional

1,253 reviews(1,253 reviews)

$26 off

$171 nightly

The current price is $237 total

$237 total

Total with taxes and fees

Tue, Sep 22 - Wed, Sep 23

Tue 22 of September 2026 to Wed 23 of September 2026

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A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

Hyatt Vacation Club at Beach House, Key West

Key West

Pool
Hot tub

9.49.4 out of 10

Exceptionalexceptional

1,217 reviews(1,217 reviews)

$28 off

$179 nightly

The current price is $246 total

$246 total

Total with taxes and fees

Thu, Oct 8 - Fri, Oct 9

Thu 8 of October 2026 to Fri 9 of October 2026

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A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions.

A two-story building with a covered entrance, palm trees, and a bench outside.

VIP Access

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Pool

9.29.2 out of 10

Wonderfulwonderful

1,395 reviews(1,395 reviews)

$215 nightly

The current price is $293 total

$293 total

Total with taxes and fees

Mon, Aug 31 - Tue, Sep 1

Mon 31 of August 2026 to Tue 1 of September 2026

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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 Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

Photo gallery for Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns