
Upper Matecumbe Key Holidays
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Upper Matecumbe Key Holiday
Upper Matecumbe Key Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Our pick of the best Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$405 per night from 21 Aug to 22 Aug
AU$405
21 Aug - 22 Aug
includes taxes & fees
9/10 Wonderful! (1,138 reviews)
"So this is my first time visiting Cheeca Lodge- I have alway"
Reviewed on 28 Jul. 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$320 per night from 12 Aug to 13 Aug
AU$320
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,477 reviews)
"It was new, loved the balcony. Beach sports were nice but needed more lifejacket sizes. Pool amenities were great. Breakfast was good."
Reviewed on 30 Jul. 2025

Islander Resort
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$469 per night from 11 Aug to 12 Aug
AU$469
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Amazing resort and staff. Felt like I was on a tropical island and in a whole other world. Food was amazing! Rooms were beautiful and beds were super comfortable. Would definitely be coming back!"
Reviewed on 28 Jul. 2025
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.
Frequently asked questions
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Activities
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.