Upper Matecumbe Key Vacations from $420

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The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Flow Miami Hotel
Creekside Inn
Bay Breeze Premium Apartments By Eskape Collection
Casablanca Miami Beach
Cavalier Hotel South Beach
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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
$242 nightly
The price is $273 total per night from Feb 2 to Feb 3
$273 total
Feb 2 - Feb 3
Total with taxes and fees
9.2/10 Wonderful! (1,651 reviews)
Gorgeous view, very pleasant staff, clean room

Reviewed on Jan 30, 2026

Chesapeake Beach 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
$346 nightly
The price is $390 total per night from Feb 2 to Feb 3
$390 total
Feb 2 - Feb 3
Total with taxes and fees
9.2/10 Wonderful! (1,289 reviews)
Great staff and beautiful property

Reviewed on Jan 29, 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$306 nightly
The price is $345 total per night from Feb 8 to Feb 9
$345 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,275 reviews)
The grounds are very well kept, the front desk staff were all very friendly and knowledgeable. The view from the ocen front room was just beautiful. The room and the halls could use a little love but other than that, a perfect stay.

Reviewed on Jan 26, 2026

Amara Cay Resort
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.