Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$315 nightly
The price is $354 total per night from Apr 29 to Apr 30
$354 total
Apr 29 - Apr 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! (1,310 reviews)
Amazing! Loved everything can’t wait to go back!!
Reviewed on Apr 5, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$262 nightly
The price is $294 total per night from May 4 to May 5
$294 total
May 4 - May 5
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! (1,689 reviews)
Beautiful property and the beach is nice, calm, and quiet. The made to order breakfasts every morning were absolutely amazing and delicious! My only complaint was that we explored Islamorada and did adventures during the day off the property. When we came back after dinnertime, we wanted to use some ...
Reviewed on Apr 7, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$288 nightly
The price is $325 total per night from Apr 21 to Apr 22
$325 total
Apr 21 - Apr 22
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! (1,267 reviews)
Great
Reviewed on Mar 30, 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! (652 reviews)
Very good
Reviewed on Apr 6, 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 ...
9.8/10 Exceptional! (73 reviews)
Phenomenal hotel, Marcel and Jackie were amazing with the kids and the activities offered. This is the first hotel where I feel there is great value in the resort fee with all that's included.
Reviewed on Mar 9, 2026
Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (113 reviews)
We had such a great experience at this oceanfront cottage! The property was very clean and was well equipped with everything we needed. A great location in the middle of everything that's great about Islamorada - we biked and walked most places. Owner was very responsive and helpful. We hope to stay ...
Reviewed on Mar 23, 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.
Check Upper Matecumbe Key hotel availability
Popular places to visit
Bud n' Mary's Dive Center
4.5/5(142 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
- MoradaWay Arts & Cultural District
- Matecumbe United Methodist Church
- Hurricane Monument
- Everglades National Park
- Baker's Cay Resort Beach
- John Pennekamp Coral Reef State Park
- Jimmy Johnson's Big Chill
- Fiesta Key
- Anne's Beach
- Long Key State Park
- Harry Harris Park
- Florida Keys Dive Center
- Pigeon Key
- Bluefin Rock Harbor Marina
- Founders Park
- Islamorada County Park
- Windley Key Fossil Reef Geological State Park
- Jacob's Aquatic Center
- Sunset Drive Beach