Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$190 nightly
The price is $214 total per night from Sep 23 to Sep 24
$214 total
Sep 23 - Sep 24
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! (1,442 reviews)
"Loved the room, quiet vibe, designated parking, the water front area, and staff. Nice surrounding area. You need a car if you want to go to Key West or nearby cities. If you want activity recommend planning ahead. We were celebrating wedding anniversary and this fit the bill. Loved it and would come ..."
Reviewed on Sep 21, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$187 nightly
The price is $210 total per night from Oct 21 to Oct 22
$210 total
Oct 21 - Oct 22
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. ...
9.2/10 Wonderful! (1,780 reviews)
"Beautiful sunrise on their beach"
Reviewed on Sep 21, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$206 nightly
The price is $232 total per night from Sep 27 to Sep 28
$232 total
Sep 27 - Sep 28
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 ...
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! (749 reviews)
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."
Reviewed on Sep 20, 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 ...
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! (175 reviews)
"Amazing location and well equipped. Loved the local vibe, didn't see a manatee but plenty of green iguanas. Property was comfortable with great AC."
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.
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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
- Hurricane Monument
- Matecumbe United Methodist Church
- 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
- Long Key State Park
- Islamorada County Park
- Florida Keys Dive Center
- Jacob's Aquatic Center
- Windley Key Fossil Reef Geological State Park
- Bluefin Rock Harbor Marina
- Pigeon Key
- Sunset Drive Beach
- Alligator Reef Lighthouse
- Old Road Gallery