Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$226 nightly
The price is $246 total per night from Nov 19 to Nov 20
$246 total
Nov 19 - Nov 20
Total with taxes and 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 ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$188 nightly
The price is $212 total per night from Nov 8 to Nov 9
$212 total
Nov 8 - Nov 9
Total with taxes and 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. ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$220 nightly
The price is $248 total per night from Nov 15 to Nov 16
$248 total
Nov 15 - Nov 16
Total with taxes and 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 ...
8.8/10 Excellent! (1,326 reviews)
"Great property however the rooms could use an update."
Reviewed on Oct 25, 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.
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
Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (120 reviews)
"A"
Reviewed on Oct 18, 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
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.
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- Founders Park
- Hurricane Monument
- Bud n' Mary's Dive Center
- Florida Keys Brewing Co.
- Islamorada Brewery & Distillery
- History of Diving Museum
- Hurricane Monument
- MoradaWay Arts & Cultural District
- Matecumbe United Methodist Church
- Everglades National Park
- John Pennekamp Coral Reef State Park
- Baker's Cay Resort Beach
- Anne's Beach
- Long Key State Park
- Fiesta Key
- Jacob's Aquatic Center
- Founders Park
- Harry Harris Park
- Islamorada County Park
- Pigeon Key
- Bluefin Rock Harbor Marina
- Florida Keys Dive Center
- Windley Key Fossil Reef Geological State Park
- Sunset Drive Beach
- Alligator Reef Lighthouse
