Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$221 nightly
The price is $249 total per night from Jan 4 to Jan 5
$249 total
Jan 4 - Jan 5, 2026
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! (1,599 reviews)
The breakfasts are great
Reviewed on Dec 19, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$271 nightly
The price is $305 total per night from Jan 8 to Jan 9
$305 total
Jan 8 - Jan 9, 2026
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)
I would give this hotel one the highest ratings for my most recent stays in the area. The views were spectacular. All of the staff were very friendly and helpful. Very very minor thing was the condition of the furniture and electrical sockets weren't the best quality but I just loved everything else ...
Reviewed on Dec 16, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$420 nightly
The price is $473 total per night from Jan 3 to Jan 4
$473 total
Jan 3 - Jan 4, 2026
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! (1,266 reviews)
Everything was awsome
Reviewed on Dec 7, 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! (586 reviews)
The room was fantastically clean and the view from the balcony / sunrise was beautiful. It was everything we need for our stay to make it very enjoyable. The wild life in the area was a great bonus. We Loved watching the pelicans and spent the afternoon sat beside a host of iguanas
Reviewed on Dec 15, 2025
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! (69 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on Nov 25, 2025
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this 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! (117 reviews)
I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore.
Reviewed on Nov 25, 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.
- History of Diving Museum
- Islamorada Brewery & Distillery
- Matecumbe United Methodist Church
- Hurricane Monument
- MoradaWay Arts & Cultural District
- 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
- Islamorada County Park
- Florida Keys Dive Center
- Bluefin Rock Harbor Marina
- Harry Harris Park
- Pigeon Key
- Windley Key Fossil Reef Geological State Park
- Jacob's Aquatic Center
- Sunset Drive Beach
