
Upper Matecumbe Key Vacations from $556
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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 $5,492, price is now $2,126 per person
$2,126
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
5.8/10 (322 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

President Hotel
South Beach
Price was $2,869, price is now $1,256 per person
$1,256
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
Nice and helpful front desk staff
1 block from Ocean Drive and the heart of South Beach
Small touch for the birthday guest
Full breakfast
Reviewed on Apr 7, 2026


Carillon Miami Wellness Resort
North Beach
Price was $1,637, price is now $745 per person
$745
per person
Jun 14 - Jun 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (788 reviews)
Everything about this place is just wonderful! It started with the staff on check in. The room was so nice and clean. The view was not right in front of the room, but still a great view. The housekeeping was fantastic. The health and spa check in was welcoming and the spa experience was a total removal from the everyday stress of life. My daughter and I also loved the pool and hot tub. Again the staff there was amazing as well. The beach is area from the beach and there is a boardwalk and fitness area to enjoy. Our Easter was extra special thanks to this experience.
Reviewed on Apr 7, 2026
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View all tripsDiscover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center
4.5/5(142 reviews)
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
4.5/5(51 reviews)
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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$315 nightly
The price is $354 total per night from Apr 29 to Apr 30
$354 total
Apr 29 - Apr 30
Total with taxes and fees
9.2/10 Wonderful! (1,310 reviews)
Amazing! Loved everything can’t wait to go back!!
Reviewed on Apr 5, 2026

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$262 nightly
The price is $294 total per night from May 4 to May 5
$294 total
May 4 - May 5
Total with taxes and fees
9.2/10 Wonderful! (1,690 reviews)
Beautiful property and the beach is nice, calm, and quiet. The made to order breakfasts every morning were absolutely amazing and delicious! My only complaint was that we explored Islamorada and did adventures during the day off the property. When we came back after dinnertime, we wanted to use some ...
Reviewed on Apr 7, 2026

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$291 nightly
The price is $328 total per night from Apr 20 to Apr 21
$328 total
Apr 20 - Apr 21
Total with taxes and fees
8.8/10 Excellent! (1,267 reviews)
Great
Reviewed on Mar 30, 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.



















