Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$214 nightly
The price is $241 total per night from Sep 7 to Sep 8
$241 total
Sep 7 - Sep 8
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 ...
9.2/10 Wonderful! (1,415 reviews)
"Everything was fabulous. We stayed in a newer building on the beach. The room, service, and staff were all 10/10. Shout out to Dee at the atlantics edge restaurant for her great dinner service. Our room was clean and replenished daily. The pool and poolside service also excellent. The only downside ..."
Reviewed on Aug 30, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$197 nightly
The price is $221 total per night from Sep 8 to Sep 9
$221 total
Sep 8 - Sep 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
$206 nightly
The price is $232 total per night from Sep 15 to Sep 16
$232 total
Sep 15 - Sep 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! (1,298 reviews)
"Our stay at Amara Cay Resort was not as expected. The location was nice, and the personnel friendly. However, there were several areas that could use significant improvement, especially considering the price. My biggest concern was the pool area. There was no personnel supervising the pool, and I ..."
Reviewed on Aug 29, 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 ...
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Islamorada FL
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
10/10 Exceptional! (67 reviews)
"Absolutely amazing rental! The location is incredible, we loved being able to walk to so many shops and restaurants! Publix is right around the corner! The pool gets just the right amount of shade and sun! We have already rebooked!!"
Reviewed on Aug 4, 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! (119 reviews)
"Beautiful home!! Had everything we needed for our 7 night stay. We will definitely be back."
Reviewed on Aug 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.
Stay near popular Upper Matecumbe Key attractions
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- Visit Lower Matecumbe Key
- Visit Conch Key
- Visit Key Colony Beach
- Visit North Key Largo
- Florida Keys Brewing Co.
- Visit Tavernier
- Visit Layton
- Visit Marathon
- Visit Little Torch Key
- Visit Pirates Cove
- Visit Naranja
- Visit Florida City
- Visit Grassy Key
- Visit Islamorada
- Visit Anglers Park
- Visit Matecumbe
- Visit Lower Matecumbe Beach
- Islamorada Vacations
- Sombrero Beach
- Visit Little Venice
- Visit Ramrod Key
- Visit Bahia Honda Key
- Visit Flamingo
- Visit Long Key
- Visit Big Pine Key
- Visit Plantation Key
- Visit Homestead
- Visit Princeton
- Visit Lignumvitae Key Botanical State Park
- Visit Duck Key
- Key Largo Vacations
- Visit Seabreeze Trailer Park
- All inclusive Vacation Packages Key Largo
- Visit Tingler Island
- Hurricane Monument
- Visit Key Largo
- Bud n' Mary's Dive Center
- Islamorada Brewery & Distillery
- Florida Keys Brewing Co.
- History of Diving Museum
- MoradaWay Arts & Cultural District
- Matecumbe United Methodist Church
- Hurricane Monument
- Baker's Cay Resort Beach
- Everglades National Park
- John Pennekamp Coral Reef State Park
- Jimmy Johnson's Big Chill
- Fiesta Key
- Anne's Beach
- Founders Park
- Islamorada County Park
- Long Key State Park
- Florida Keys Dive Center
- Pigeon Key
- Harry Harris Park
- Windley Key Fossil Reef Geological State Park
- Bluefin Rock Harbor Marina
- Jacob's Aquatic Center
- Alligator Reef Lighthouse
- Sunset Drive Beach
