Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$9,583 per night from Apr 29 to Apr 30
NT$9,583
NT$13,125 total
Apr 29 - Apr 30
includes taxes & 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! (1,304 reviews)
N/A
Reviewed on 2026/3/29
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is NT$7,886 per night from Apr 14 to Apr 15
NT$7,886
NT$10,675 total
Apr 14 - Apr 15
includes taxes & 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! (1,680 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 2026/3/31
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is NT$9,930 per night from Apr 15 to Apr 16
NT$9,930
NT$13,515 total
Apr 15 - Apr 16
includes taxes & 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! (1,266 reviews)
Great
Reviewed on 2026/3/30
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! (648 reviews)
First, the location is excellent! Lovely peaceful spot with a sandy palm studded 'beach' offering Atlantic ocean views of Alligator Reef Lighthouse. Clean rooms, big screen porches, great views from the Oceanside apartments. They had what we needed in the kitchen and bath, but just the basics which ...
Reviewed on 2026/4/1
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 2026/3/9
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (148 reviews)
Amazing stay!
Reviewed on 2026/3/31
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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- Eco Pond
- Sunset Drive Beach
- Visit Key Largo
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- Founders Park
- Visit Duck Key
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- Visit Homestead
- Jimmy Johnson's Big Chill
- Visit Big Pine Key
- Flamingo Visitor Center
- Buttonwood Canal
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- Visit Pirates Cove
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- Visit Little Venice
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