Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $280 total per night from Jan 28 to Jan 29
$280 total
Jan 28 - Jan 29
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! (1,625 reviews)
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!
Reviewed on Jan 6, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$317 nightly
The price is $357 total per night from Jan 29 to Jan 30
$357 total
Jan 29 - Jan 30
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! (1,284 reviews)
Fantastic resort, will definitely be heading back!
Reviewed on Jan 4, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$295 nightly
The price is $332 total per night from Jan 11 to Jan 12
$332 total
Jan 11 - Jan 12
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! (1,273 reviews)
All issues were addressed quickly and professionally. Room was large/ spacious. Views were gorgeous. Tiki bar staff was awesome.
Reviewed on Jan 4, 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! (603 reviews)
The one bedroom apartment was large and very clean. I loved the balcony with the view of the dock and the entire property was nice and well kept. Short drive to market and restaurants. Would definitely stay again and would recommend to others.
Reviewed on Jan 3, 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on Nov 25, 2025
New - Oceanfront Estate - Private Beach - Heated Pool - Stunning
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 ...
Upon arrival, we were amazed at the beauty of the location of the home. Everything was in prestine condition. The pool and beach are minutes away from the back door. We experienced a plethora of restaurants on the island. The owners were wonderful to work with. We definitely will be returning.
Reviewed on Oct 16, 2025
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
Popular places to visit
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
Hurricane Monument
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Bud n' Mary's Dive Center
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
Islamorada Brewery & Distillery
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
Keys History & Discovery Center
You can spend time exploring the galleries in Keys History & Discovery Center during your trip to Islamorada.
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- 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
- Fiesta Key
- Anne's Beach
- Long Key State Park
- Founders Park
- Florida Keys Dive Center
- Bluefin Rock Harbor Marina
- Islamorada County Park
- Windley Key Fossil Reef Geological State Park
- Pigeon Key
- Harry Harris Park
- Jacob's Aquatic Center
- Sunset Drive Beach