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

3 nights
from Sun, Aug 23 · $115/night
$346
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1Low$3542$3653$4594$5685$5906$4307$4018$3979$39710$46911$48512$46813$46714$40115$39216$45417$49818$53019$54320$51021$41422$41623$44124$49025$52226$52127$48428$37529$37530$375
Cheapest dayCheaperMidPriciest

Hotels for Fri, Dec 25

  • Heron House Court

    Heron House Court

    4.4Pleasant · 366 reviews
    $1,165
    $388/night · 3n
    Book
  • Havana Cabana

    Havana Cabana

    4.2Pleasant · 2,918 reviews
    $1,339
    $446/night · 3n
    Book
  • The Perry Hotel & Marina Key West

    The Perry Hotel & Marina Key West

    4.5Pleasant · 1,642 reviews
    $1,357
    $452/night · 3n
    Book
  • NYAH Key West

    NYAH Key West

    3.9Pleasant · 1,502 reviews
    $1,369
    $456/night · 3n
    Book
  • Seashell Motel

    Seashell Motel

    3.7Pleasant · 814 reviews
    $1,456
    $485/night · 3n
    Book
  • Hampton Inn Key West

    Hampton Inn Key West

    4.3Pleasant · 1,367 reviews
    $1,492
    $497/night · 3n
    Book
  • The Southernmost Inn

    The Southernmost Inn

    3.8Pleasant · 839 reviews
    $1,530
    $510/night · 3n
    Book
  • Simonton Court Hotel Key West

    Simonton Court Hotel Key West

    4.8Pleasant · 540 reviews
    $1,539
    $513/night · 3n
    Book
  • DoubleTree Resort by Hilton Hotel Grand Key - Key West

    DoubleTree Resort by Hilton Hotel Grand Key - Key West

    4.0Pleasant · 2,822 reviews
    $1,669
    $556/night · 3n
    Book
  • Casablanca Hotel Key West

    Casablanca Hotel Key West

    4.6Pleasant · 361 reviews
    $1,675
    $558/night · 3n
    Book
  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3.7Pleasant · 2,607 reviews
    $1,733
    $578/night · 3n
    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
    $1,752
    $584/night · 3n
    Book
  • Southernmost Beach Resort & Guesthouses

    Southernmost Beach Resort & Guesthouses

    4.1Pleasant · 4,074 reviews
    $1,887
    $629/night · 3n
    Book
  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    4.1Pleasant · 2,420 reviews
    $1,968
    $656/night · 3n
    Book
  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    4.3Pleasant · 2,411 reviews
    $2,011
    $670/night · 3n
    Book
  • Courtyard by Marriott Key West Waterfront

    Courtyard by Marriott Key West Waterfront

    4.2Pleasant · 1,443 reviews
    $2,208
    $736/night · 3n
    Book
  • The Capitana Key West

    The Capitana Key West

    4.6Pleasant · 1,082 reviews
    $2,223
    $741/night · 3n
    Book
  • Beachside Resort & Residences

    Beachside Resort & Residences

    4.3Pleasant · 3,584 reviews
    $2,705
    $902/night · 3n
    Book
  • The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    3.9Pleasant · 1,173 reviews
    $2,749
    $916/night · 3n
    Book
  • Lighthouse Hotel - Key West Historic Inns

    Lighthouse Hotel - Key West Historic Inns

    4.4Pleasant · 780 reviews
    $3,062
    $1,021/night · 3n
    Book
  • Casa Marina Key West, Curio Collection by Hilton

    Casa Marina Key West, Curio Collection by Hilton

    3.7Pleasant · 4,470 reviews
    $3,426
    $1,142/night · 3n
    Book
  • Ocean Key Resort & Spa

    Ocean Key Resort & Spa

    4.6Pleasant · 2,399 reviews
    $3,736
    $1,245/night · 3n
    Book
  • Hyatt Centric Key West Resort & Spa

    Hyatt Centric Key West Resort & Spa

    4.4Pleasant · 1,869 reviews
    $3,841
    $1,280/night · 3n
    Book

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