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

June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Cheapest dayCheaperMidPriciest

Hotels for Sat, Sep 5

  • Authors Guesthouse Key West

    Authors Guesthouse Key West

    4.3Pleasant · 352 reviews
    $328
    $164/night · 2n
    Book
  • Heron House Court

    Heron House Court

    4.4Pleasant · 366 reviews
    $343
    $172/night · 2n
    Book
  • Southwinds Motel

    Southwinds Motel

    4.2Pleasant · 1,068 reviews
    $362
    $181/night · 2n
    Book
  • NYAH Key West

    NYAH Key West

    3.9Pleasant · 1,502 reviews
    $375
    $188/night · 2n
    Book
  • Beachside Resort & Residences

    Beachside Resort & Residences

    4.3Pleasant · 3,584 reviews
    $385
    $193/night · 2n
    Book
  • Seashell Motel

    Seashell Motel

    3.7Pleasant · 814 reviews
    $386
    $193/night · 2n
    Book
  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3.7Pleasant · 2,607 reviews
    $410
    $205/night · 2n
    Book
  • Hampton Inn Key West

    Hampton Inn Key West

    4.3Pleasant · 1,367 reviews
    $418
    $209/night · 2n
    Book
  • The Southernmost Inn

    The Southernmost Inn

    3.8Pleasant · 839 reviews
    $453
    $227/night · 2n
    Book
  • Havana Cabana

    Havana Cabana

    4.2Pleasant · 2,918 reviews
    $453
    $227/night · 2n
    Book
  • DoubleTree Resort by Hilton Hotel Grand Key - Key West

    DoubleTree Resort by Hilton Hotel Grand Key - Key West

    4.0Pleasant · 2,824 reviews
    $471
    $236/night · 2n
    Book
  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    4.3Pleasant · 2,411 reviews
    $494
    $247/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
    $496
    $248/night · 2n
    Book
  • The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    3.9Pleasant · 1,173 reviews
    $539
    $270/night · 2n
    Book
  • Simonton Court Hotel Key West

    Simonton Court Hotel Key West

    4.8Pleasant · 540 reviews
    $568
    $284/night · 2n
    Book
  • Casablanca Hotel Key West

    Casablanca Hotel Key West

    4.6Pleasant · 361 reviews
    $570
    $285/night · 2n
    Book
  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    4.1Pleasant · 2,421 reviews
    $576
    $288/night · 2n
    Book
  • The Perry Hotel & Marina Key West

    The Perry Hotel & Marina Key West

    4.5Pleasant · 1,642 reviews
    $651
    $326/night · 2n
    Book
  • Southernmost Beach Resort & Guesthouses

    Southernmost Beach Resort & Guesthouses

    4.1Pleasant · 4,076 reviews
    $658
    $329/night · 2n
    Book
  • The Capitana Key West

    The Capitana Key West

    4.6Pleasant · 1,083 reviews
    $664
    $332/night · 2n
    Book
  • Casa Marina Key West, Curio Collection by Hilton

    Casa Marina Key West, Curio Collection by Hilton

    3.7Pleasant · 4,471 reviews
    $705
    $353/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
    $801
    $401/night · 2n
    Book
  • Eden House Key West

    Eden House Key West

    4.5Pleasant · 629 reviews
    $831
    $416/night · 2n
    Book
  • Opal Key Resort & Marina

    Opal Key Resort & Marina

    4.5Pleasant · 4,830 reviews
    $843
    $422/night · 2n
    Book
  • Pegasus International Hotel

    Pegasus International Hotel

    3.8Pleasant · 474 reviews
    $876
    $438/night · 2n
    Book
  • Courtyard by Marriott Key West Waterfront

    Courtyard by Marriott Key West Waterfront

    4.2Pleasant · 1,443 reviews
    $900
    $450/night · 2n
    Book
  • Hyatt Centric Key West Resort & Spa

    Hyatt Centric Key West Resort & Spa

    4.4Pleasant · 1,869 reviews
    $901
    $451/night · 2n
    Book
  • Ocean Key Resort & Spa

    Ocean Key Resort & Spa

    4.6Pleasant · 2,401 reviews
    $1,087
    $544/night · 2n
    Book

More for Key West