Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$204 nightly
The price is $229 total per night from Aug 18 to Aug 19
$229 total
Aug 18 - Aug 19
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! (1,369 reviews)
"Lola at the front desk was amazing and guided us every step of the way"
Reviewed on Aug 6, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$209 nightly
The price is $235 total per night from Aug 11 to Aug 12
$235 total
Aug 11 - Aug 12
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
$219 nightly
The price is $247 total per night from Aug 16 to Aug 17
$247 total
Aug 16 - Aug 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 ...
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 ...
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! (117 reviews)
"Host was very responsive when we reached out and the place had everything we needed. The dock for the boat was very easy to get in and out of and we had plenty of room for the trailer. The place was also very clean."
Reviewed on Jun 11, 2026
Oceanfront Estate - Private Beach, Pool, & Dock
Islamorada FL
Book a stay at this beach vacation home in Islamorada. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Bud n' Mary's Dive Center and ...
10/10 Exceptional! (4 reviews)
"Our family of 10 recently stayed at this wonderful home for one week. The property was large enough to easily accommodate our group. The views are stunning, the pool and grounds are very nicely done. The screened lanai was great for extended evenings outside without worrying about bugs. Well maintained ..."
Reviewed on Jun 22, 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
- Fiesta Key
- Anne's Beach
- Founders Park
- Long Key State Park
- Islamorada County Park
- Harry Harris Park
- Pigeon Key
- Florida Keys Dive Center
- Windley Key Fossil Reef Geological State Park
- Bluefin Rock Harbor Marina
- Sunset Drive Beach
- Jacob's Aquatic Center
- Alligator Reef Lighthouse
