Islamorada Cheap Vacations

Book a Cheap Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Cheap Islamorada Hotels

Conch On Inn Motel

Conch On Inn Motel

2 out of 5
103 Caloosa Street, Tavernier, FL
  • 11 min drive from Theater of the Sea
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Old Road Gallery and Florida Keys Dive Center are ...
Great little place to call home
"Overall great experience & owners were great. Only thing I would offer up is could use some new mattresses but everything else was more than expected! Would (or shouldsay will) stay again someday"

Reviewed on Aug 6, 2018

Conch On Inn Motel
Creekside Inn Islamorada

Creekside Inn Islamorada

2.5 out of 5
90611 Old Highway, Tavernier, FL
  • 15 min drive from Theater of the Sea
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,012 reviews)
"We stayed here off season, the price was right. There is decline in the appearance of the property, looks like they may be trying to fix it up. Breakfast and the bar was closed. The office hours are hit or miss, but the ladies are sweethearts. The pool we had all to ourselves and extremely clean. ..."

Reviewed on Sep 24, 2025

Creekside Inn Islamorada
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,210 reviews)
"I love it"

Reviewed on Sep 21, 2025

Cheeca Lodge & Spa
See all 2,228 properties in Islamorada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.