Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$223 nightly
The price is $251 total per night from Jan 5 to Jan 6
$251 total
Jan 5 - Jan 6
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! (1,614 reviews)
Good location and a nice resort all in all. However, the rooms are very noisy. You can hear everything being said in the rooms around you.
Reviewed on Jan 2, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$367 nightly
The price is $413 total per night from Jan 11 to Jan 12
$413 total
Jan 11 - Jan 12
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! (1,278 reviews)
Good property but a little dated and understaffed. They are trying and they are hospitable but not a 5 star experience. Still one of the nicer resorts in the area.
Reviewed on Dec 29, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$277 nightly
The price is $312 total per night from Jan 8 to Jan 9
$312 total
Jan 8 - Jan 9
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! (1,271 reviews)
Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !
Reviewed on Dec 28, 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.
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! (602 reviews)
Extremely fast and easy check in. Room was clean with a great view
Reviewed on Jan 1, 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.
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
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.
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.
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.
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
