
Upper Matecumbe Key Vacations from $377
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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
Price was $799, price is now $377 per person
$377
per person
Aug 13 - Aug 16
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

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


The 27 Wynwood
Wynwood Art District
Save 100% on your flight
Price was $858, price is now $456 per person
$456
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
10/10 Exceptional! (5 reviews)
Property is beautiful. The rooftop top pool is amazing. Everything is really close to the main street in wynwood. Will definitely be back.
Reviewed on Jun 5, 2026

Hotel Riu Plaza Miami Beach
Mid Beach
Save 100% on your flight
Price was $880, price is now $470 per person
$470
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8/10 Very Good! (1,145 reviews)
The property is excellent from every aspects. The staffs are so helpful and they put every effort to make our family trip enjoyable. I loved the breakfast buffet as it has all options for everyone. The food choices and quantities are also exceptional. The property is on the beach and easy access to the beach. Also, it is well secured and well lighted everywhere. I loved the fact it that it is little away from the south beach which is very loud.
I don’t have much negative to say. I wish the property entry is little wider but they can’t do much about it. The lobby is wide and open. So that that covers it. Also, I wish they had more beach umbrellas as they run out fast. The swimming pool is little small and most of the time no music in the pool which some people would like.
I loved this property and I may stay here again if I come to Miami.
Reviewed on Jun 9, 2026
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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 Jun 14 to Jun 15
$342 total
Jun 14 - Jun 15
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! (1,753 reviews)
"This place was great! Very private, great amenities, staff, location, and accessible! Has everything you need for intimate location Oceanview is stellar, you can walk right into the ocean and relax with provided chairs, umbrellas, and towels. They have breakfast included with all breakfast types ..."
Reviewed on Jun 12, 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! (1,050 reviews)
"Resort was great and staff were friendly and helpful. However the resort is dated so don’t expect modern rooms. For some reason everything in the area is dated from the 50’s."
Reviewed on Jun 12, 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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