HotelDip

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

2 nights
from Sun, Aug 23 · $117/night
$234
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1Low$2362$2363$2474$3395$4376$3137$2598$2599$25810$26811$31412$32513$31414$25915$26716$26717$30018$35019$37820$34521$26722$28723$28624$29325$33126$36327$32928$25029$25030$250
Cheapest dayCheaperMidPriciest

Hotels for Fri, Dec 25

  • Heron House Court

    Heron House Court

    4.4Pleasant · 366 reviews
    $804
    $402/night · 2n
    Book
  • The Perry Hotel & Marina Key West

    The Perry Hotel & Marina Key West

    4.5Pleasant · 1,642 reviews
    $905
    $453/night · 2n
    Book
  • Havana Cabana

    Havana Cabana

    4.2Pleasant · 2,918 reviews
    $940
    $470/night · 2n
    Book
  • Hampton Inn Key West

    Hampton Inn Key West

    4.3Pleasant · 1,367 reviews
    $960
    $480/night · 2n
    Book
  • Seashell Motel

    Seashell Motel

    3.7Pleasant · 814 reviews
    $962
    $481/night · 2n
    Book
  • NYAH Key West

    NYAH Key West

    3.9Pleasant · 1,502 reviews
    $990
    $495/night · 2n
    Book
  • Simonton Court Hotel Key West

    Simonton Court Hotel Key West

    4.8Pleasant · 540 reviews
    $1,026
    $513/night · 2n
    Book
  • The Southernmost Inn

    The Southernmost Inn

    3.8Pleasant · 839 reviews
    $1,047
    $524/night · 2n
    Book
  • DoubleTree Resort by Hilton Hotel Grand Key - Key West

    DoubleTree Resort by Hilton Hotel Grand Key - Key West

    4.0Pleasant · 2,822 reviews
    $1,127
    $564/night · 2n
    Book
  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3.7Pleasant · 2,607 reviews
    $1,145
    $573/night · 2n
    Book
  • Southernmost Beach Resort & Guesthouses

    Southernmost Beach Resort & Guesthouses

    4.1Pleasant · 4,074 reviews
    $1,150
    $575/night · 2n
    Book
  • Casablanca Hotel Key West

    Casablanca Hotel Key West

    4.6Pleasant · 361 reviews
    $1,150
    $575/night · 2n
    Book
  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    4.1Pleasant · 2,420 reviews
    $1,182
    $591/night · 2n
    Book
  • Fairfield by Marriott Inn & Suites Key West at The Keys Collection

    Fairfield by Marriott Inn & Suites Key West at The Keys Collection

    4.1Pleasant · 1,983 reviews
    $1,182
    $591/night · 2n
    Book
  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    4.3Pleasant · 2,411 reviews
    $1,261
    $631/night · 2n
    Book
  • The Capitana Key West

    The Capitana Key West

    4.6Pleasant · 1,082 reviews
    $1,278
    $639/night · 2n
    Book
  • Courtyard by Marriott Key West Waterfront

    Courtyard by Marriott Key West Waterfront

    4.2Pleasant · 1,443 reviews
    $1,442
    $721/night · 2n
    Book
  • Beachside Resort & Residences

    Beachside Resort & Residences

    4.3Pleasant · 3,584 reviews
    $1,751
    $876/night · 2n
    Book
  • The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    3.9Pleasant · 1,173 reviews
    $1,815
    $908/night · 2n
    Book
  • Casa Marina Key West, Curio Collection by Hilton

    Casa Marina Key West, Curio Collection by Hilton

    3.7Pleasant · 4,469 reviews
    $2,008
    $1,004/night · 2n
    Book
  • Lighthouse Hotel - Key West Historic Inns

    Lighthouse Hotel - Key West Historic Inns

    4.4Pleasant · 780 reviews
    $2,190
    $1,095/night · 2n
    Book
  • Ocean Key Resort & Spa

    Ocean Key Resort & Spa

    4.6Pleasant · 2,399 reviews
    $2,446
    $1,223/night · 2n
    Book
  • Hyatt Centric Key West Resort & Spa

    Hyatt Centric Key West Resort & Spa

    4.4Pleasant · 1,869 reviews
    $2,656
    $1,328/night · 2n
    Book

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