Upper Matecumbe Key Holidays

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Top hotels in Upper Matecumbe Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €181 per night from 17 Sept to 18 Sept
€181
17 Sept - 18 Sept
includes taxes & fees
9/10 Wonderful! (1,196 reviews)
"all good"

Reviewed on 10 Sept 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €165 per night from 17 Sept to 18 Sept
€165
17 Sept - 18 Sept
includes taxes & fees
9.2/10 Wonderful! (1,529 reviews)
Relaxation 😌
"Such a relaxing and fun spot. Enjoyed snorkeling every day at sunrise and sunset 😍 Can't wait for my next stay 🤗"

Reviewed on 15 Sept 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €217 per night from 21 Sept to 22 Sept
€217
21 Sept - 22 Sept
includes taxes & fees
8.8/10 Excellent! (1,249 reviews)
"Everyone was so nice there"

Reviewed on 6 Sept 2025

Amara Cay Resort
See all 2,798 properties in Upper Matecumbe Key
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.

Bud n' Mary's Dive Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.