Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is S$509 per night from 1 Mar to 2 Mar
S$509
1 Mar - 2 Mar
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! (1,666 reviews)
Clean rooms, friendly staff. Liked that coffee, tea and water available 24 hours. However, we felt the cost was very expensive.
Reviewed on 20 Feb, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is S$611 per night from 3 Mar to 4 Mar
S$611
3 Mar - 4 Mar
includes taxes & fees
Stay at this 5-star 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! (1,307 reviews)
Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus
Reviewed on 17 Feb, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is S$473 per night from 25 Feb to 26 Feb
S$473
25 Feb - 26 Feb
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! (1,263 reviews)
Great
Reviewed on 20 Feb, 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! (622 reviews)
Clean room friendly and helpful staff proximity to many attractions
Reviewed on 20 Feb, 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 ...
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (132 reviews)
Treasure Harbor was just fantastic. Everything was perfect! We can't wait to visit again and stay longer.
Reviewed on 20 Feb, 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
4.5/5(3 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
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
3/5(2 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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