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 Wed, Sep 23

  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3.7Pleasant · 2,607 reviews
    $243
    $122/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
    $286
    $143/night · 2n
    Book
  • Southwinds Motel

    Southwinds Motel

    4.2Pleasant · 1,068 reviews
    $286
    $143/night · 2n
    Book
  • Authors Guesthouse Key West

    Authors Guesthouse Key West

    4.3Pleasant · 352 reviews
    $298
    $149/night · 2n
    Book
  • Casablanca Hotel Key West

    Casablanca Hotel Key West

    4.6Pleasant · 361 reviews
    $310
    $155/night · 2n
    Book
  • Beachside Resort & Residences

    Beachside Resort & Residences

    4.3Pleasant · 3,584 reviews
    $318
    $159/night · 2n
    Book
  • The Southernmost Inn

    The Southernmost Inn

    3.8Pleasant · 839 reviews
    $322
    $161/night · 2n
    Book
  • Seashell Motel

    Seashell Motel

    3.7Pleasant · 814 reviews
    $325
    $163/night · 2n
    Book
  • NYAH Key West

    NYAH Key West

    3.9Pleasant · 1,502 reviews
    $329
    $165/night · 2n
    Book
  • Hampton Inn Key West

    Hampton Inn Key West

    4.3Pleasant · 1,367 reviews
    $329
    $165/night · 2n
    Book
  • Heron House Court

    Heron House Court

    4.4Pleasant · 366 reviews
    $338
    $169/night · 2n
    Book
  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    4.3Pleasant · 2,411 reviews
    $351
    $176/night · 2n
    Book
  • The Perry Hotel & Marina Key West

    The Perry Hotel & Marina Key West

    4.5Pleasant · 1,642 reviews
    $361
    $181/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
    $368
    $184/night · 2n
    Book
  • Havana Cabana

    Havana Cabana

    4.2Pleasant · 2,918 reviews
    $378
    $189/night · 2n
    Book
  • Eden House Key West

    Eden House Key West

    4.5Pleasant · 629 reviews
    $392
    $196/night · 2n
    Book
  • The Saint Hotel Key West, Autograph Collection, Adult Only

    The Saint Hotel Key West, Autograph Collection, Adult Only

    4.5Pleasant · 663 reviews
    $401
    $201/night · 2n
    Book
  • Southernmost Beach Resort & Guesthouses

    Southernmost Beach Resort & Guesthouses

    4.1Pleasant · 4,074 reviews
    $414
    $207/night · 2n
    Book
  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    4.1Pleasant · 2,420 reviews
    $430
    $215/night · 2n
    Book
  • Lighthouse Hotel - Key West Historic Inns

    Lighthouse Hotel - Key West Historic Inns

    4.4Pleasant · 780 reviews
    $432
    $216/night · 2n
    Book
  • The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    3.9Pleasant · 1,173 reviews
    $439
    $220/night · 2n
    Book
  • Ibis Bay Beach Resort

    Ibis Bay Beach Resort

    4.0Pleasant · 4,340 reviews
    $486
    $243/night · 2n
    Book
  • Simonton Court Hotel Key West

    Simonton Court Hotel Key West

    4.8Pleasant · 540 reviews
    $514
    $257/night · 2n
    Book
  • The Capitana Key West

    The Capitana Key West

    4.6Pleasant · 1,082 reviews
    $523
    $262/night · 2n
    Book
  • Pier House Resort & Spa

    Pier House Resort & Spa

    4.4Pleasant · 1,920 reviews
    $553
    $277/night · 2n
    Book
  • Casa Marina Key West, Curio Collection by Hilton

    Casa Marina Key West, Curio Collection by Hilton

    3.7Pleasant · 4,469 reviews
    $565
    $283/night · 2n
    Book
  • Ocean Key Resort & Spa

    Ocean Key Resort & Spa

    4.6Pleasant · 2,399 reviews
    $608
    $304/night · 2n
    Book
  • Hyatt Centric Key West Resort & Spa

    Hyatt Centric Key West Resort & Spa

    4.4Pleasant · 1,869 reviews
    $631
    $316/night · 2n
    Book
  • Opal Key Resort & Marina

    Opal Key Resort & Marina

    4.5Pleasant · 4,829 reviews
    $773
    $387/night · 2n
    Book
  • Courtyard by Marriott Key West Waterfront

    Courtyard by Marriott Key West Waterfront

    4.2Pleasant · 1,443 reviews
    $791
    $396/night · 2n
    Book

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