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 Mon, Dec 28

Sort

Heron House Court
4.4Pleasant · 366 reviews
$1,094
$365/night · 3n
Book
Southwinds Motel
4.2Pleasant · 1,068 reviews
$1,158
$386/night · 3n
Book
Havana Cabana
4.2Pleasant · 2,918 reviews
$1,197
$399/night · 3n
Book
Hampton Inn Key West
4.3Pleasant · 1,367 reviews
$1,357
$452/night · 3n
Book
NYAH Key West
3.9Pleasant · 1,502 reviews
$1,372
$457/night · 3n
Book
The Southernmost Inn
3.8Pleasant · 839 reviews
$1,378
$459/night · 3n
Book
Seashell Motel
3.7Pleasant · 814 reviews
$1,632
$544/night · 3n
Book
DoubleTree Resort by Hilton Hotel Grand Key - Key West
4.0Pleasant · 2,822 reviews
$1,680
$560/night · 3n
Book
The Perry Hotel & Marina Key West
4.5Pleasant · 1,642 reviews
$1,718
$573/night · 3n
Book
Casablanca Hotel Key West
4.6Pleasant · 361 reviews
$1,795
$598/night · 3n
Book
Hilton Garden Inn Key West / The Keys Collection
3.7Pleasant · 2,607 reviews
$1,855
$618/night · 3n
Book
Simonton Court Hotel Key West
4.8Pleasant · 540 reviews
$1,918
$639/night · 3n
Book
Southernmost Beach Resort & Guesthouses
4.1Pleasant · 4,074 reviews
$1,953
$651/night · 3n
Book
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
4.1Pleasant · 1,983 reviews
$2,011
$670/night · 3n
Book
Eden House Key West
4.5Pleasant · 629 reviews
$2,041
$680/night · 3n
Book
Courtyard by Marriott Key West Waterfront
4.2Pleasant · 1,443 reviews
$2,347
$782/night · 3n
Book
Parrot Key Hotel & Villas
4.3Pleasant · 2,411 reviews
$2,378
$793/night · 3n
Book
Margaritaville Beach House Key West
4.1Pleasant · 2,420 reviews
$2,601
$867/night · 3n
Book
Lighthouse Hotel - Key West Historic Inns
4.4Pleasant · 780 reviews
$2,687
$896/night · 3n
Book
Beachside Resort & Residences
4.3Pleasant · 3,584 reviews
$2,851
$950/night · 3n
Book
The Reach Key West, Curio Collection by Hilton
3.9Pleasant · 1,173 reviews
$3,168
$1,056/night · 3n
Book
The Capitana Key West
4.6Pleasant · 1,082 reviews
$3,422
$1,141/night · 3n
Book
Hyatt Centric Key West Resort & Spa
4.4Pleasant · 1,869 reviews
$3,508
$1,169/night · 3n
Book
Casa Marina Key West, Curio Collection by Hilton
3.7Pleasant · 4,470 reviews
$3,934
$1,311/night · 3n
Book
Ocean Key Resort & Spa
4.6Pleasant · 2,399 reviews
$4,052
$1,351/night · 3n
Book

More for Key West

Best time to visit Key West Luxury in Key West 5-star in Key West Cheap in Key West Beachfront in Key West Spa in Key West Pet-friendly in Key West