Cheapest dates for Any class hotels in Key West

Stay flexible and book the dip. Greener days are cheaper, so tap a day to see hotels.

Cheapest stays in the next 3 months

from Sun, Aug 23 · $115/night

June 2026

Sun

Mon

Tue

Wed

Thu

Fri

Sat

1Low$354 2$365 3$459 4$568 5$590 6$430 7$401 8$397 9$397 10$469 11$485 12$468 13$467 14$401 15$392 16$454 17$498 18$530 19$543 20$510 21$414 22$416 23$441 24$490 25$522 26$521 27$484 28$375 29$375 30$375

Cheapest dayCheaperMidPriciest

Hotels for Sun, Dec 27

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Heron House Court
4.4Pleasant · 366 reviews
$1,096
$365/night · 3n
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Southwinds Motel
4.2Pleasant · 1,068 reviews
$1,131
$377/night · 3n
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Havana Cabana
4.2Pleasant · 2,918 reviews
$1,197
$399/night · 3n
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NYAH Key West
3.9Pleasant · 1,502 reviews
$1,240
$413/night · 3n
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Hampton Inn Key West
4.3Pleasant · 1,367 reviews
$1,364
$455/night · 3n
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The Southernmost Inn
3.8Pleasant · 839 reviews
$1,457
$486/night · 3n
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Seashell Motel
3.7Pleasant · 814 reviews
$1,510
$503/night · 3n
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Casablanca Hotel Key West
4.6Pleasant · 361 reviews
$1,575
$525/night · 3n
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The Perry Hotel & Marina Key West
4.5Pleasant · 1,642 reviews
$1,599
$533/night · 3n
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DoubleTree Resort by Hilton Hotel Grand Key - Key West
4.0Pleasant · 2,822 reviews
$1,605
$535/night · 3n
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Hilton Garden Inn Key West / The Keys Collection
3.7Pleasant · 2,607 reviews
$1,764
$588/night · 3n
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Fairfield by Marriott Inn & Suites Key West at The Keys Collection
4.1Pleasant · 1,983 reviews
$1,867
$622/night · 3n
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Simonton Court Hotel Key West
4.8Pleasant · 540 reviews
$1,973
$658/night · 3n
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Southernmost Beach Resort & Guesthouses
4.1Pleasant · 4,074 reviews
$2,049
$683/night · 3n
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Eden House Key West
4.5Pleasant · 629 reviews
$2,103
$701/night · 3n
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Courtyard by Marriott Key West Waterfront
4.2Pleasant · 1,443 reviews
$2,317
$772/night · 3n
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Parrot Key Hotel & Villas
4.3Pleasant · 2,411 reviews
$2,348
$783/night · 3n
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Margaritaville Beach House Key West
4.1Pleasant · 2,420 reviews
$2,512
$837/night · 3n
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Beachside Resort & Residences
4.3Pleasant · 3,584 reviews
$2,818
$939/night · 3n
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Lighthouse Hotel - Key West Historic Inns
4.4Pleasant · 780 reviews
$2,839
$946/night · 3n
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The Reach Key West, Curio Collection by Hilton
3.9Pleasant · 1,173 reviews
$2,935
$978/night · 3n
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The Capitana Key West
4.6Pleasant · 1,082 reviews
$3,193
$1,064/night · 3n
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Hyatt Centric Key West Resort & Spa
4.4Pleasant · 1,869 reviews
$3,585
$1,195/night · 3n
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Casa Marina Key West, Curio Collection by Hilton
3.7Pleasant · 4,470 reviews
$3,883
$1,294/night · 3n
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Ocean Key Resort & Spa
4.6Pleasant · 2,399 reviews
$4,092
$1,364/night · 3n
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