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

7 nights
from Sun, Aug 23 · $125/night
$874
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1$1,2082$1,1143$1,1474$1,1805$1,2056Low$1,0417$1,0418$1,0429$1,07810$1,09011$1,08312$1,07513$1,11914$1,12815$1,15016$1,16217$1,17318$1,18419$1,19120$1,16521$1,11722$1,12823$1,13124$1,11725$1,12526$1,12327$1,17028$1,24829$1,24430$1,243
Cheapest dayCheaperMidPriciest

Hotels for Tue, Oct 27

  • Southwinds Motel

    Southwinds Motel

    4.2Pleasant · 1,068 reviews
    $1,418
    $203/night · 7n
    Book
  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3.7Pleasant · 2,607 reviews
    $1,457
    $208/night · 7n
    Book
  • Authors Guesthouse Key West

    Authors Guesthouse Key West

    4.3Pleasant · 352 reviews
    $1,473
    $210/night · 7n
    Book
  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    4.3Pleasant · 2,411 reviews
    $1,500
    $214/night · 7n
    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
    $1,509
    $216/night · 7n
    Book
  • Hampton Inn Key West

    Hampton Inn Key West

    4.3Pleasant · 1,367 reviews
    $1,564
    $223/night · 7n
    Book
  • Havana Cabana

    Havana Cabana

    4.2Pleasant · 2,918 reviews
    $1,613
    $230/night · 7n
    Book
  • DoubleTree Resort by Hilton Hotel Grand Key - Key West

    DoubleTree Resort by Hilton Hotel Grand Key - Key West

    4.0Pleasant · 2,822 reviews
    $1,644
    $235/night · 7n
    Book
  • The Southernmost Inn

    The Southernmost Inn

    3.8Pleasant · 839 reviews
    $1,645
    $235/night · 7n
    Book
  • Casablanca Hotel Key West

    Casablanca Hotel Key West

    4.6Pleasant · 361 reviews
    $1,654
    $236/night · 7n
    Book
  • Beachside Resort & Residences

    Beachside Resort & Residences

    4.3Pleasant · 3,584 reviews
    $1,739
    $248/night · 7n
    Book
  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    4.1Pleasant · 2,420 reviews
    $1,841
    $263/night · 7n
    Book
  • Southernmost Beach Resort & Guesthouses

    Southernmost Beach Resort & Guesthouses

    4.1Pleasant · 4,074 reviews
    $1,869
    $267/night · 7n
    Book
  • The Perry Hotel & Marina Key West

    The Perry Hotel & Marina Key West

    4.5Pleasant · 1,642 reviews
    $1,920
    $274/night · 7n
    Book
  • NYAH Key West

    NYAH Key West

    3.9Pleasant · 1,502 reviews
    $1,927
    $275/night · 7n
    Book
  • Lighthouse Hotel - Key West Historic Inns

    Lighthouse Hotel - Key West Historic Inns

    4.4Pleasant · 780 reviews
    $2,207
    $315/night · 7n
    Book
  • Ibis Bay Beach Resort

    Ibis Bay Beach Resort

    4.0Pleasant · 4,340 reviews
    $2,235
    $319/night · 7n
    Book
  • The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    3.9Pleasant · 1,173 reviews
    $2,310
    $330/night · 7n
    Book
  • Seashell Motel

    Seashell Motel

    3.7Pleasant · 814 reviews
    $2,333
    $333/night · 7n
    Book
  • The Capitana Key West

    The Capitana Key West

    4.6Pleasant · 1,082 reviews
    $2,428
    $347/night · 7n
    Book
  • Eden House Key West

    Eden House Key West

    4.5Pleasant · 629 reviews
    $2,512
    $359/night · 7n
    Book
  • Casa Marina Key West, Curio Collection by Hilton

    Casa Marina Key West, Curio Collection by Hilton

    3.7Pleasant · 4,469 reviews
    $2,704
    $386/night · 7n
    Book
  • Pier House Resort & Spa

    Pier House Resort & Spa

    4.4Pleasant · 1,920 reviews
    $2,865
    $409/night · 7n
    Book
  • Courtyard by Marriott Key West Waterfront

    Courtyard by Marriott Key West Waterfront

    4.2Pleasant · 1,443 reviews
    $2,916
    $417/night · 7n
    Book
  • Simonton Court Hotel Key West

    Simonton Court Hotel Key West

    4.8Pleasant · 540 reviews
    $2,927
    $418/night · 7n
    Book
  • Hyatt Centric Key West Resort & Spa

    Hyatt Centric Key West Resort & Spa

    4.4Pleasant · 1,869 reviews
    $3,020
    $431/night · 7n
    Book
  • Ocean Key Resort & Spa

    Ocean Key Resort & Spa

    4.6Pleasant · 2,399 reviews
    $3,176
    $454/night · 7n
    Book
  • Opal Key Resort & Marina

    Opal Key Resort & Marina

    4.5Pleasant · 4,829 reviews
    $3,343
    $478/night · 7n
    Book

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