Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$370 nightly
The price is $417 total per night from Mar 1 to Mar 2
$417 total
Mar 1 - Mar 2
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! (1,666 reviews)
Clean rooms, friendly staff. Liked that coffee, tea and water available 24 hours. However, we felt the cost was very expensive.
Reviewed on Feb 20, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$428 nightly
The price is $482 total per night from Mar 3 to Mar 4
$482 total
Mar 3 - Mar 4
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! (1,307 reviews)
Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus
Reviewed on Feb 17, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$328 nightly
The price is $370 total per night from Feb 25 to Feb 26
$370 total
Feb 25 - Feb 26
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! (1,263 reviews)
Great
Reviewed on Feb 20, 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! (622 reviews)
Clean room friendly and helpful staff proximity to many attractions
Reviewed on Feb 20, 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 ...
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 ...
10/10 Exceptional! (1 review)
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.
Popular places to visit
Bud n' Mary's Dive Center
4.5/5(141 reviews)
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 family-friendly area.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
4.5/5(51 reviews)
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.
Matecumbe United Methodist Church
After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.
Hurricane Monument
4/5(66 reviews)
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Islamorada Brewery & Distillery
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
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- Bud n' Mary's Dive Center
- Florida Keys Brewing Co.
- Islamorada Brewery & Distillery
- History of Diving Museum
- Matecumbe United Methodist Church
- MoradaWay Arts & Cultural District
- Hurricane Monument
- 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
- Islamorada County Park
- Harry Harris Park
- Bluefin Rock Harbor Marina
- Florida Keys Dive Center
- Pigeon Key
- Founders Park
- Windley Key Fossil Reef Geological State Park
- Sunset Drive Beach
- Jacob's Aquatic Center
