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 · $117/night

June 2026

Sun

Mon

Tue

Wed

Thu

Fri

Sat

1Low$236 2$236 3$247 4$339 5$437 6$313 7$259 8$259 9$258 10$268 11$314 12$325 13$314 14$259 15$267 16$267 17$300 18$350 19$378 20$345 21$267 22$287 23$286 24$293 25$331 26$363 27$329 28$250 29$250 30$250

Cheapest dayCheaperMidPriciest

Hotels for Mon, Dec 28

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Heron House Court
4.4Pleasant · 366 reviews
$735
$368/night · 2n
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Southwinds Motel
4.2Pleasant · 1,068 reviews
$754
$377/night · 2n
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Havana Cabana
4.2Pleasant · 2,918 reviews
$798
$399/night · 2n
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NYAH Key West
3.9Pleasant · 1,502 reviews
$864
$432/night · 2n
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Hampton Inn Key West
4.3Pleasant · 1,367 reviews
$876
$438/night · 2n
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The Southernmost Inn
3.8Pleasant · 839 reviews
$974
$487/night · 2n
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Seashell Motel
3.7Pleasant · 814 reviews
$1,016
$508/night · 2n
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Casablanca Hotel Key West
4.6Pleasant · 361 reviews
$1,050
$525/night · 2n
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DoubleTree Resort by Hilton Hotel Grand Key - Key West
4.0Pleasant · 2,822 reviews
$1,073
$537/night · 2n
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Hilton Garden Inn Key West / The Keys Collection
3.7Pleasant · 2,607 reviews
$1,112
$556/night · 2n
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The Perry Hotel & Marina Key West
4.5Pleasant · 1,642 reviews
$1,146
$573/night · 2n
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Fairfield by Marriott Inn & Suites Key West at The Keys Collection
4.1Pleasant · 1,983 reviews
$1,297
$649/night · 2n
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Southernmost Beach Resort & Guesthouses
4.1Pleasant · 4,074 reviews
$1,312
$656/night · 2n
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Eden House Key West
4.5Pleasant · 629 reviews
$1,372
$686/night · 2n
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Simonton Court Hotel Key West
4.8Pleasant · 540 reviews
$1,460
$730/night · 2n
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Courtyard by Marriott Key West Waterfront
4.2Pleasant · 1,443 reviews
$1,551
$776/night · 2n
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Parrot Key Hotel & Villas
4.3Pleasant · 2,411 reviews
$1,588
$794/night · 2n
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Margaritaville Beach House Key West
4.1Pleasant · 2,420 reviews
$1,779
$890/night · 2n
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Beachside Resort & Residences
4.3Pleasant · 3,584 reviews
$1,864
$932/night · 2n
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The Reach Key West, Curio Collection by Hilton
3.9Pleasant · 1,173 reviews
$1,957
$979/night · 2n
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Lighthouse Hotel - Key West Historic Inns
4.4Pleasant · 780 reviews
$1,967
$984/night · 2n
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The Capitana Key West
4.6Pleasant · 1,082 reviews
$2,248
$1,124/night · 2n
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Hyatt Centric Key West Resort & Spa
4.4Pleasant · 1,869 reviews
$2,400
$1,200/night · 2n
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Ocean Key Resort & Spa
4.6Pleasant · 2,399 reviews
$2,494
$1,247/night · 2n
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Casa Marina Key West, Curio Collection by Hilton
3.7Pleasant · 4,469 reviews
$2,660
$1,330/night · 2n
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