
Upper Matecumbe Key Vacations from $503
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The Latest Upper Matecumbe Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Place Miami Airport-East
Palmer Lake
Save 100% on your flight
Price was $946, price is now $503 per person
$503
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (2,247 reviews)
Room was nice, clean and beautiful view of the airport. A little noisy because of the airport but was nice. Never got to try the breakfast as we had an early flight. Easy check in process, will hold luggage so you don’t have to hold it till you get to check in.
Reviewed on Feb 3, 2026

Casablanca Miami Beach
North Beach
Price was $1,404, price is now $643 per person
$643
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly
Reviewed on Nov 12, 2025



Cavalier Hotel South Beach
South Beach
Price was $1,315, price is now $686 per person
$686
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Prime location within walking distance to all the hot spots. Included are 2 beach chairs with towels per day. Philip at the concierge received us warmly…checking us in early and giving us great recommendations. Room was a great size, A/C, with bathroom amenities. Overall, totally recommend.
Reviewed on Jan 31, 2026
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See all available trips from Columbus to Upper Matecumbe Key
View all tripsDiscover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.

Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

History of Diving Museum
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
Upper Matecumbe Key Hotel Deals

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$362 nightly
The price is $408 total per night from Feb 11 to Feb 12
$408 total
Feb 11 - Feb 12
Total with taxes and fees
9.2/10 Wonderful! (1,665 reviews)
We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.
Reviewed on Feb 3, 2026

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$448 nightly
The price is $505 total per night from Feb 10 to Feb 11
$505 total
Feb 10 - Feb 11
Total with taxes and fees
9.2/10 Wonderful! (1,294 reviews)
We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa ...
Reviewed on Feb 4, 2026

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$303 nightly
The price is $341 total per night from Feb 11 to Feb 12
$341 total
Feb 11 - Feb 12
Total with taxes and fees
8.8/10 Excellent! (1,263 reviews)
All good, nice bartender inside downstairs, and easy walk to fish and eat
Reviewed on Feb 5, 2026
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.



















