Upper Matecumbe Key Vacations from $409

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The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Miami Downtown Condos
Bay Breeze Premium Apartments By Eskape Collection
The Retreat Collection at 1 Hotel & Homes South Beach
The Shelborne By Proper, a Member of Design Hotels
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Discover the most popular places to visit in Upper Matecumbe Key

Upper Matecumbe Key Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $249 total per night from Jan 14 to Jan 15
$249 total
Jan 14 - Jan 15
Total with taxes and fees
9.2/10 Wonderful! (1,609 reviews)
Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return.

Reviewed on Dec 31, 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
$277 nightly
The price is $312 total per night from Jan 8 to Jan 9
$312 total
Jan 8 - Jan 9
Total with taxes and fees
8.8/10 Excellent! (1,271 reviews)
Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !

Reviewed on Dec 28, 2025

Amara Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$322 nightly
The price is $363 total per night from Jan 15 to Jan 16
$363 total
Jan 15 - Jan 16
Total with taxes and fees
9.2/10 Wonderful! (1,278 reviews)
Good property but a little dated and understaffed. They are trying and they are hospitable but not a 5 star experience. Still one of the nicer resorts in the area.

Reviewed on Dec 29, 2025

Cheeca Lodge & Spa
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.

Find the Best Upper Matecumbe Key Vacation Packages

Upper Matecumbe Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.