Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €357 per night from 29 Apr to 30 Apr
€357
29 Apr - 30 Apr
includes taxes & fees
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 in their ...
9.2/10 Wonderful! (1,304 reviews)
N/A
Reviewed on 29 Mar 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is €288 per night from 28 Apr to 29 Apr
€288
28 Apr - 29 Apr
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,680 reviews)
Good location in Islamorada close to attractions and good midpoint for exploring the keys. The property has the old building, motel style by the road and newer buildings and villas a bit more modern. Breakfast gets a bit backed up so go early if you want omelets, pancakes or French toast (the warm ...
Reviewed on 31 Mar 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is €319 per night from 19 Apr to 20 Apr
€319
19 Apr - 20 Apr
includes taxes & fees
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 their reviews. ...
8.8/10 Excellent! (1,266 reviews)
Great
Reviewed on 30 Mar 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
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (647 reviews)
We stayed in the one bedroom apartment ground floor with screened back patio. It was very spacious and comfortable. I especially liked the screened in patio. It was great for reading and just relaxing. It has a full kitchen including toaster, blender, and microwave, which was nice. A close walk to ...
Reviewed on 31 Mar 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
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 9 Mar 2026
Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, 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 23 Mar 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
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.
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
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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