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 · $124/night
$870
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1$1,3012$1,1143$1,1474$1,1805$1,2136Low$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$1,12122$1,13523$1,13824$1,12725$1,13826$1,13627$1,18928$1,25529$1,24630$1,247
Cheapest dayCheaperMidPriciest

Hotels for Wed, Dec 16

  • Southwinds Motel

    Southwinds Motel

    4.2Pleasant · 1,068 reviews
    $1,517
    $217/night · 7n
    Book
  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    4.3Pleasant · 2,411 reviews
    $1,626
    $232/night · 7n
    Book
  • Havana Cabana

    Havana Cabana

    4.2Pleasant · 2,918 reviews
    $1,641
    $234/night · 7n
    Book
  • The Southernmost Inn

    The Southernmost Inn

    3.8Pleasant · 839 reviews
    $1,749
    $250/night · 7n
    Book
  • NYAH Key West

    NYAH Key West

    3.9Pleasant · 1,502 reviews
    $1,769
    $253/night · 7n
    Book
  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3.7Pleasant · 2,607 reviews
    $1,789
    $256/night · 7n
    Book
  • Ibis Bay Beach Resort

    Ibis Bay Beach Resort

    4.0Pleasant · 4,340 reviews
    $1,979
    $283/night · 7n
    Book
  • Seashell Motel

    Seashell Motel

    3.7Pleasant · 814 reviews
    $2,032
    $290/night · 7n
    Book
  • Southernmost Beach Resort & Guesthouses

    Southernmost Beach Resort & Guesthouses

    4.1Pleasant · 4,074 reviews
    $2,037
    $291/night · 7n
    Book
  • Casablanca Hotel Key West

    Casablanca Hotel Key West

    4.6Pleasant · 361 reviews
    $2,058
    $294/night · 7n
    Book
  • Authors Guesthouse Key West

    Authors Guesthouse Key West

    4.3Pleasant · 352 reviews
    $2,086
    $298/night · 7n
    Book
  • Hampton Inn Key West

    Hampton Inn Key West

    4.3Pleasant · 1,367 reviews
    $2,097
    $300/night · 7n
    Book
  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    4.1Pleasant · 2,420 reviews
    $2,129
    $304/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
    $2,138
    $305/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
    $2,151
    $307/night · 7n
    Book
  • Beachside Resort & Residences

    Beachside Resort & Residences

    4.3Pleasant · 3,584 reviews
    $2,185
    $312/night · 7n
    Book
  • The Perry Hotel & Marina Key West

    The Perry Hotel & Marina Key West

    4.5Pleasant · 1,642 reviews
    $2,236
    $319/night · 7n
    Book
  • Eden House Key West

    Eden House Key West

    4.5Pleasant · 629 reviews
    $2,302
    $329/night · 7n
    Book
  • The Capitana Key West

    The Capitana Key West

    4.6Pleasant · 1,082 reviews
    $2,454
    $351/night · 7n
    Book
  • Simonton Court Hotel Key West

    Simonton Court Hotel Key West

    4.8Pleasant · 540 reviews
    $2,497
    $357/night · 7n
    Book
  • Courtyard by Marriott Key West Waterfront

    Courtyard by Marriott Key West Waterfront

    4.2Pleasant · 1,443 reviews
    $2,943
    $420/night · 7n
    Book
  • The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    3.9Pleasant · 1,173 reviews
    $3,158
    $451/night · 7n
    Book
  • Opal Key Resort & Marina

    Opal Key Resort & Marina

    4.5Pleasant · 4,830 reviews
    $3,398
    $485/night · 7n
    Book
  • Hyatt Centric Key West Resort & Spa

    Hyatt Centric Key West Resort & Spa

    4.4Pleasant · 1,869 reviews
    $3,861
    $552/night · 7n
    Book
  • Ocean Key Resort & Spa

    Ocean Key Resort & Spa

    4.6Pleasant · 2,399 reviews
    $4,336
    $619/night · 7n
    Book
  • Casa Marina Key West, Curio Collection by Hilton

    Casa Marina Key West, Curio Collection by Hilton

    3.7Pleasant · 4,470 reviews
    $4,748
    $678/night · 7n
    Book
  • Lighthouse Hotel - Key West Historic Inns

    Lighthouse Hotel - Key West Historic Inns

    4.4Pleasant · 780 reviews
    $4,956
    $708/night · 7n
    Book

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