Plan, book, travel with confidence
Better together
Save up to ₩9,995 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
Upper Matecumbe Key Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩318,170 per night from Jun 25 to Jun 26
₩318,170
per night
Jun 25 - Jun 26
8.8/10 Excellent! (1,333 reviews)
"We really enjoyed it, staff was very nice and property was nice and clean. It has 2 pools and beach access. We would definitely come back!"
Reviewed on May 26, 2024
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩339,873 per night from Jun 4 to Jun 5
₩339,873
per night
Jun 4 - Jun 5
8.8/10 Excellent! (1,000 reviews)
Perfect location
"Lovely experience. A place we will come back to visit."
Reviewed on May 26, 2024
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩356,371 per night from Jul 1 to Jul 2
₩356,371
per night
Jul 1 - Jul 2
8.8/10 Excellent! (1,234 reviews)
"They are under new management and have made some nice changes. Beach towels are now by the pool, metal water bottles are given at check in and water stations are available to refill them. Free shuttle service is offered within a range. We used it every night to take us to dinner. Lunch at the pool ..."
Reviewed on May 27, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Upper Matecumbe Key
Everglades National Park
This sprawling wetland park holds a seemingly endless supply of wildlife habitats and enthralling ecosystems.
Theater of the Sea
4.5/5(215 reviews)
Swim with the dolphins and sharks and feed the crocodiles and sea turtles near the lagoon of this vast interactive park for marine mammals.
Anne's Beach
3.5/5(139 reviews)
If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.