Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is NT$13,706 per night from Mar 1 to Mar 2
NT$13,706
NT$17,188 total
Mar 1 - Mar 2
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! (1,675 reviews)
Nice stay
Reviewed on 2026/2/10
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$11,913 per night from Feb 22 to Feb 23
NT$11,913
NT$15,701 total
Feb 22 - Feb 23
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! (1,301 reviews)
Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.
Reviewed on 2026/2/9
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is NT$11,648 per night from Feb 25 to Feb 26
NT$11,648
NT$15,403 total
Feb 25 - Feb 26
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! (1,270 reviews)
Great staff, good view from room and breakfast was superb. Thanks.
Reviewed on 2026/2/10
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! (618 reviews)
Old-Florida style accommodations, very clean. Staff helpful and friendly. The beach offers lots of wildlife viewing. Great location, great value
Reviewed on 2026/2/10
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! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on 2025/11/25
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! (129 reviews)
The place was very clean and well set up. The amenities were there however the weather didn’t cooperate. I would definitely recommend it to anyone wanting to stay in the Florida Keys.
Reviewed on 2026/1/30
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.
Check Upper Matecumbe Key hotel availability
Popular places to visit
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.
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.
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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- Eco Pond
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- Visit Key Largo
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- Visit Duck Key
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- Jimmy Johnson's Big Chill
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- Buttonwood Canal
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- Visit Pirates Cove
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- Visit Little Venice
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