
Upper Matecumbe Key Vacations from $417
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The Latest Upper Matecumbe Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $833, price is now $417 per person
$417
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
Super cute and great location. Waiting staff was great and front was nice but a little lack of communication. Our room air wasn’t working really well so they switched our room and comp our breakfast the rest of the stay.
Reviewed on Jun 3, 2026

Miami Downtown Condos
Downtown Miami
Price was $1,692, price is now $431 per person
$431
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (171 reviews)
We booked this option as a place to begin a cruise. It's conveniently located close to cruise port, Bayside and bus route to the beach. The unit was clean and modern with a view of the city. We loved the option to cook and be able to do some last minute laundry before heading for our cruise. We didn't appreciate the wopping 300 deposit requested nor did we enjoy the smell of cannabis wafting from the elevators or hallways. There are no smoking signs posted but they're obviously being ignored. Everyone deserves fresh and clean air!! The other negative was the blind in the main room was broken and so we couldn't view the city from that area. Overall, the condo served our purpose but we wouldn't make it a choice for future travels.
Reviewed on May 26, 2026

Casablanca Miami Beach
North Beach
Price was $6,946, price is now $2,920 per person
$2,920
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.8/10 (324 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.

Hurricane Monument
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$336 nightly
The price is $378 total per night from Jul 5 to Jul 6
$378 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,325 reviews)
"Ok"
Reviewed on Jun 12, 2026

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$230 nightly
The price is $258 total per night from Jun 18 to Jun 19
$258 total
Jun 18 - Jun 19
Total with taxes and fees
9.2/10 Wonderful! (1,752 reviews)
"I liked that I could fish in peace with very good resuts.I also enjoyed the free omlette."
Reviewed on Jun 11, 2026

Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$316 nightly
The price is $356 total per night from Jun 21 to Jun 22
$356 total
Jun 21 - Jun 22
Total with taxes and fees
9.4/10 Exceptional! (1,048 reviews)
"Beautiful resort with amazing grounds. Bedrooms are spacious, comfortable and modern."
Reviewed on Jun 11, 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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