Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$374 nightly
The price is $421 total per night from Apr 12 to Apr 13
$421 total
Apr 12 - Apr 13
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 ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$273 nightly
The price is $308 total per night from Apr 21 to Apr 22
$308 total
Apr 21 - Apr 22
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! (1,670 reviews)
So I did like our stay. However, we didn’t sleep great because the air conditioner is right at the foot of the master bedroom and it blows wind in your face constantly. We reached out to the property manager and he didn’t help us because it was broken and wouldn’t work the way intended. So overall ...
Reviewed on Mar 20, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$291 nightly
The price is $328 total per night from Apr 20 to Apr 21
$328 total
Apr 20 - Apr 21
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! (1,255 reviews)
Room was small
Reviewed on Mar 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! (640 reviews)
Overall, the room was clean and renovated. The checking process was a little bit of an issue...given that our room /unit was given to somebody else, but eventually the other party was willing to trade with us. It would have been helpful ahead of time to let customers know that the unit or room does ...
Reviewed on Mar 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 ...
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! (112 reviews)
Perfect location with beautiful views and sunrises
Reviewed on Jan 14, 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.
Popular places to visit
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 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
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.
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.
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
- Hurricane Monument
- Matecumbe United Methodist Church
- 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
- Pigeon Key
- Islamorada County Park
- Florida Keys Dive Center
- Harry Harris Park
- Bluefin Rock Harbor Marina
- Founders Park
- Windley Key Fossil Reef Geological State Park
- Sunset Drive Beach
- Jacob's Aquatic Center
- Molasses Reef
