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 $254 total per night from Oct 20 to Oct 21
$254 total
Oct 20 - Oct 21
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 Oct 18 to Oct 19
$212 total
Oct 18 - Oct 19
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. ...
Islander Resort
82100 Overseas Highway Islamorada FL
$281 nightly
The price is $316 total per night from Oct 18 to Oct 19
$316 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
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! (768 reviews)
"The property was clean and extremely well lit. The parking was great. The room had a full kitchen which was a huge plus. The layout of the room and the furnishings were beautiful and up to date. The room was spacious and comfortable. The staff were friendly and hospitable. I didnt pay much attention ..."
Reviewed on Oct 13, 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
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! (178 reviews)
"They bent over backwards for us, we enjoyed the stay. Everyone should try it."
Reviewed on Oct 10, 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.
Check Upper Matecumbe Key hotel availability
Stay near popular Upper Matecumbe Key attractions
Explore a world of travel with Expedia
- Hotels in Islamorada
- Hotels in Tavernier
- All-Inclusive in Islamorada
- Houseboats in Islamorada
- Hotels in Layton
- 5 Star Hotels in Islamorada
- Ocean View in Islamorada
- Marriott Hotels & Resorts Hotels in Islamorada
- Motels in Islamorada
- Hilton Hotels in Islamorada
- 4 Star Hotels in Islamorada
- Hotels in Long Key
- Oceanic Airlines Norfolk (ORF) to Marathon (MTH) flights
- Flights to Tavernier
- Flights to Key Largo
- Flights from Fort Lauderdale (FLL) to Marathon (MTH)
- Flights to Upper Matecumbe Key
- Flights to Islamorada
- Oceanic Airlines Sarasota (SRQ) to Marathon (MTH) flights
- Flights from Miami (MIA) to Marathon (MTH)
- Flights to Duck Key
- Flights to Layton
- Key Largo All Inclusive Vacation Packages
- Where to stay in Plantation Key
- Upper Matecumbe Key All Inclusive Vacation Packages
- Visit Marathon
- Visit Layton
- Visit Key Colony Beach
- Upper Matecumbe Key All Inclusive Vacation Packages
- Visit Key Largo
- Visit Duck Key
- Where to stay in Key Colony Beach
- Key Largo All Inclusive Vacation Packages
- Where to stay in Tavernier
- Where to stay in Lower Matecumbe Key
- Where to stay in Marathon
- Where to stay in Florida City
- Marathon Vacations
- Windley Key All Inclusive Vacation Packages
- Where to stay in Upper Matecumbe Key
- Upper Matecumbe Key All Inclusive Vacation Packages
- Visit North Key Largo
- Where to stay in Key Largo
- Visit Seabreeze Trailer Park
- Key Largo All Inclusive Vacation Packages
- Visit Islamorada
- Windley Key All Inclusive Vacation Packages
- Islamorada Vacations
- Visit Plantation Key
- Bud n' Mary's Dive Center
- Visit Lignumvitae Key Botanical
- History of Diving Museum
- Tavernier Vacations
- Visit Long Key
- Duck Key All Inclusive Vacation Packages
- Where to stay in Homestead
- Florida City Vacations
- Visit Conch Key
- Long Key Vacations
- Key Largo All Inclusive Vacation Packages
- Visit Tavernier
- Where to stay in Windley Key
- Visit Anglers Park
- Visit Grassy Key
- Visit Lower Matecumbe Key
- Where to stay in Lower Arsnicker Keys
- Key Largo Vacations
- Lignumvitae Key Botanical All Inclusive Vacation Packages
- 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
- Jimmy Johnson's Big Chill
- Anne's Beach
- Long Key State Park
- Jacob's Aquatic Center
- Founders Park
- Fiesta Key
- Harry Harris Park
- Pigeon Key
- Islamorada County Park
- Bluefin Rock Harbor Marina
- Florida Keys Dive Center
- Windley Key Fossil Reef Geological State Park
- Sunset Drive Beach
- Alligator Reef Lighthouse
- Old Road Gallery