Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is ₩241,851 per night from Nov 29 to Nov 30
₩241,851
₩369,636 total
Nov 29 - Nov 30
includes taxes & fees
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! (1,502 reviews)
"Food was excellent and staff was extremely friendly. The room could have been a little better. The floors were sandy but the room was otherwise clean"
Reviewed on Nov 3, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is ₩201,498 per night from Nov 10 to Nov 11
₩201,498
₩301,721 total
Nov 10 - Nov 11
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.4/10 Exceptional! (1,808 reviews)
"This resort was the perfect getaway for us!! Ocean front! Beautiful views!!"
Reviewed on Nov 2, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is ₩224,209 per night from Nov 15 to Nov 16
₩224,209
₩349,789 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
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.
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (777 reviews)
"Right on the ocean. Beautiful views. Very relaxing. Not busy this time of year and it was great."
Reviewed on Oct 22, 2026
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (180 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
Reviewed on Oct 23, 2026
Island Bay Resort
92530 OVERSEAS HIGHWAY Tavernier FL
Book a stay at this beach aparthotel in Tavernier. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
10/10 Exceptional! (187 reviews)
"The air conditioning leaked in the bedroom down the wall and floor. I came close to slipped the first night. Had to place all our towels on the floor after."
Reviewed on Nov 1, 2026
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.
