Upper Matecumbe Key Vacations from $366

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The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Brickell Arch Sea View Balcony Free Parking by Palermo Home Miami
Casablanca Miami Beach
The Retreat Collection at 1 Hotel & Homes South Beach
AKA Brickell High Floor Free Parking by Palermo Home
Nobu Hotel Miami Beach
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Stay near popular Upper Matecumbe Key attractions

Upper Matecumbe Key Hotel Deals

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
$232 nightly
The price is $261 total per night from Jul 16 to Jul 17
$261 total
Jul 16 - Jul 17
Total with taxes and fees
9.2/10 Wonderful! (1,339 reviews)
"The room and property are clean and the staff is friendly and helpful."

Reviewed on Jul 7, 2026

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
$222 nightly
The price is $250 total per night from Aug 3 to Aug 4
$250 total
Aug 3 - Aug 4
Total with taxes and fees
9.2/10 Wonderful! (1,740 reviews)
"Very nice rooms, very important for us is having a good AC in the room and it was perfect. 2nd time I had stay in this hotel and I will stay again."

Reviewed on Jul 7, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$234 nightly
The price is $263 total per night from Jul 13 to Jul 14
$263 total
Jul 13 - Jul 14
Total with taxes and fees
8.8/10 Excellent! (1,287 reviews)
"Thw hotel is not what it used to be. Smell terrible . Fans in all thr floors due to leaks . Room service is ordered now through text ."

Reviewed on Jul 5, 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.