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 S$255 per night from 25 Sept to 26 Sept
S$255
25 Sept - 26 Sept
includes taxes & fees
9/10 Wonderful! (1,198 reviews)
Very Nice Resort and AMAZING STAFF!
"Honestly, we started with a pretty bad experience with some issues pertaining to our room. However, we mentioned it to Natalia at the concierge and she was SUPER accommodating! Needless to say that the issues were resolved immediately. Definitely recommend Cheeca Lodge & Spa to anyone looking for ..."

Reviewed on 16 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 S$235 per night from 25 Sept to 26 Sept
S$235
25 Sept - 26 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 S$319 per night from 25 Sept to 26 Sept
S$319
25 Sept - 26 Sept
includes taxes & fees
8.8/10 Excellent! (1,248 reviews)
"Great hotel with a perfect location and friendly staff."

Reviewed on 13 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

History of Diving Museum

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.

History of Diving Museum

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