Islamorada Cheap Vacations

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

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

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

Top Cheap Islamorada Hotels

Creekside Inn

Creekside Inn

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! (1,000 reviews)
The staff were very friendly and helpful

Reviewed on Jan 5, 2026

Creekside Inn
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 8 min drive from Theater of the Sea
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,288 reviews)
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

Cheeca Lodge & Spa
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
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.