Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$207 nightly
The price is $233 total per night from Oct 4 to Oct 5
$233 total
Oct 4 - Oct 5
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
Fully refundable
$180 nightly
The price is $202 total per night from Sep 30 to Oct 1
$202 total
Sep 30 - Oct 1
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
$212 nightly
The price is $238 total per night from Sep 16 to Sep 17
$238 total
Sep 16 - Sep 17
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! (1,315 reviews)
"I like Everything!"
Reviewed on Sep 9, 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 ...
8.8/10 Excellent! (743 reviews)
"Very nice and clean rooms, very spacious, Beautiful Ocean View."
Reviewed on Sep 9, 2026
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 ...
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.
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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
- Everglades National Park
- Baker's Cay Resort Beach
- John Pennekamp Coral Reef State Park
- Jimmy Johnson's Big Chill
- Anne's Beach
- Fiesta Key
- Founders Park
- Harry Harris Park
- Islamorada County Park
- Long Key State Park
- Florida Keys Dive Center
- Jacob's Aquatic Center
- Bluefin Rock Harbor Marina
- Windley Key Fossil Reef Geological State Park
- Pigeon Key
- Sunset Drive Beach
- Alligator Reef Lighthouse