Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
$259 nightly
The price is $291 total per night from Nov 3 to Nov 4
$291 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,265 reviews)
Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.
Reviewed on Oct 30, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
$165 nightly
The price is $186 total per night from Nov 5 to Nov 6
$186 total
Nov 5 - Nov 6
Total with taxes and fees
Stay at this 3.5-star 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! (1,548 reviews)
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.
Reviewed on Oct 27, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$205 nightly
The price is $231 total per night from Nov 30 to Dec 1
$231 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,270 reviews)
We enjoyed our stay a beautiful place, but there was no free breakfast
Reviewed on Oct 24, 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 ...
8.6/10 Excellent! (551 reviews)
Peaceful stay
Absolutely loved my stay. However, the beds are not the most comfortable. That is my only complaint.
Reviewed on Oct 27, 2025
The Islands of Islamorada
82779 Old Hwy, Islamorada, FL
Stay at this 4-star 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! (68 reviews)
i like the fact that there's beach area but it was difficult to walk in an out of it due to the rocks. The pool filter could have been cleaned during our stay as there was multiple days of debris caught in the drain trap. would have enjoyed more dining options. Room was available before check in ...
Reviewed on Oct 27, 2025
Treasure Harbor
200 Treasure Harbor Dr, Islamorada, FL
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (108 reviews)
Brand new houseboats, very clean & comfortable, new pool area which was great to relax & have a dip. Lots of wildlife in vicinity
Reviewed on Oct 10, 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
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.
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.
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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
- Jimmy Johnson's Big Chill
- Baker's Cay Resort Beach
- Fiesta Key
- Anne's Beach
- Long Key State Park
- Islamorada County Park
- Founders Park
- Harry Harris Park
- Florida Keys Dive Center
- Windley Key Fossil Reef Geological State Park
- Pigeon Key
- Bluefin Rock Harbor Marina
- Sunset Drive Beach
- Jacob's Aquatic Center