Upper Matecumbe Key Vacations from $378

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The Latest Upper Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG
The W - Bayshore Unit 1003
Casablanca Miami Beach
Brickell Bay 3318
Cavalier Hotel South Beach
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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
$258 nightly
The price is $290 total per night from Jun 7 to Jun 8
$290 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (1,318 reviews)
"Cheeca Lodge is my absolute favorite place in The Keys The property is gorgeous, I love the amenities, the complimentary kayaking, bikes & champagne for Mother’s Day was such a nice touch The rooms are so cozy, just love it there. Ask for Rob at the pool bar, he makes a great drink!"

Reviewed on Jun 4, 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
$233 nightly
The price is $262 total per night from Jun 9 to Jun 10
$262 total
Jun 9 - Jun 10
Total with taxes and fees
9.2/10 Wonderful! (1,740 reviews)
"The resort is in a great location, clean and well maintained. Our king suite was very comfortable, had a large, lovely bathroom, balcony with a great view of the ocean. Breakfast with made to order omelets and pancakes, as well as breads, muffins, cold cereals, juices, and a nice area to eat on the ..."

Reviewed on Jun 5, 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jun 14 to Jun 15
$329 total
Jun 14 - Jun 15
Total with taxes and fees
9.4/10 Exceptional! (1,035 reviews)
"Un poco costosa para lo que era pero todo bien"

Reviewed on Jun 5, 2026

Islander 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.