Upper Matecumbe Key Cheap Vacations
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Flight and Cheap hotel deals in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $10,113
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Fontainebleau Miami Beach
Mid Beach
CA $1,695
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very good! (8,706 reviews)
Top tier it’s worth it rather you going for a good time family time intimacy just some good old fun or some me time. This the place to be.
Reviewed on Aug 18, 2026
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View all trips5* Cheap holidays in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $10,113
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
1 Hotel South Beach
South Beach
CA $3,603
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
Everything about this hotel is AMAZING especially the staff! I definitely recommend this hotel, I can’t wait to come back with my kiddos!
Reviewed on Aug 16, 2026
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View all trips3 Night Cheap holidays in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $9,411
per person
Nov 12 - Nov 15
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
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See all available trips from Columbus to Upper Matecumbe Key
View all trips4 Night Cheap holidays in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $10,113
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
1 Hotel South Beach
South Beach
CA $3,603
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
Everything about this hotel is AMAZING especially the staff! I definitely recommend this hotel, I can’t wait to come back with my kiddos!
Reviewed on Aug 16, 2026
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See all available trips from Columbus to Upper Matecumbe Key
View all tripsCheap Hotels in Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
- 10 min drive from Bud n' Mary's Dive Center
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
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.
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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.
