
Upper Matecumbe Key Vacations from $615
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The Latest Upper Matecumbe Key vacation packages
Price found within the past 48 hours. Click for updated prices.





Casablanca Miami Beach
North Beach
Price was $6,866, price is now $2,904 per person
$2,904
per person
Jul 23 - Jul 28
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.8/10 (323 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 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 family-friendly 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
$240 nightly
The price is $270 total per night from May 21 to May 22
$270 total
May 21 - May 22
Total with taxes and fees
9.2/10 Wonderful! (1,738 reviews)
Just
Reviewed on May 12, 2026

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$304 nightly
The price is $342 total per night from May 31 to Jun 1
$342 total
May 31 - Jun 1
Total with taxes and fees
9.2/10 Wonderful! (1,330 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026

Islander Resort
82100 Overseas Highway Islamorada FL
$250 nightly
The price is $281 total per night from May 19 to May 20
$281 total
May 19 - May 20
Total with taxes and fees
9.2/10 Wonderful! (1,013 reviews)
Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest ...
Reviewed on May 10, 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.



















