Islamorada Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to €185 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
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! (1,199 reviews)
Very Nice Resort and AMAZING STAFF!
"Honestly, we started with a pretty bad experience with some issues pertaining to our room. However, we mentioned it to Natalia at the concierge and she was SUPER accommodating! Needless to say that the issues were resolved immediately. Definitely recommend Cheeca Lodge & Spa to anyone looking for ..."

Reviewed on 16 Sept 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
  • 12 min drive from Theater of the Sea
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,249 reviews)
"Great hotel with a perfect location and friendly staff."

Reviewed on 13 Sept 2025

Amara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
  • 8 min walk from Theater of the Sea
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,003 reviews)
"Beach view"

Reviewed on 11 Sept 2025

Drop Anchor
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.