
Upper Matecumbe Key Holidays
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Top Flight + Hotel Deals in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach
South Beach
Price was €1,331, price is now €893 per person
€893
per person
7 Dec - 14 Dec
found 1 day ago
Return direct flight included
Warsaw (WAW) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
We had a great stay at the Cavalier Hotel. The interior of the hotel is beautiful. They also have a bar area as well as breakfast, lunch, and dinner options for dine-in or take-out. The beach is only a few steps away! The hotel provided beach towels as well.
Our room was clean and beds were comfortable. The bathroom doesn't have a proper door that locks. It's only a sliding door, which we found difficult for privacy.
All the staff we met were also very friendly and helpful.
The only note for anyone looking to stay at this property is that the hotel itself doesn't have any parking. There is a Municipal Parking Garage right around the corner from the hotel. We found it very convenient to park there (including overnight parking). It's open 24 hours, clean, has stairs and elevators to get to the street.
Reviewed on 28 Oct 2025


Hotel Riu Plaza Miami Beach
Mid Beach
Price was €2,260, price is now €1,395 per person
€1,395
per person
7 Dec - 14 Dec
found 1 day ago
Return direct flight included
Warsaw (WAW) to Miami (MIA)
8.2/10 Very Good! (1,118 reviews)
Just sort the lifts out. It’s a problem and has clearly been a problem for some time. Either something more sinister is going off or management are so inept and ignoring things like these annoying ratings requests that nobody ever listens to the feedback of anyway.
Reviewed on 26 Oct 2025

1 Hotel South Beach
South Beach
Save 100% on your flight
Price was €7,653, price is now €4,947 per person
€4,947
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,333 reviews)
Fantastic staff, pools and restaurants.
Reviewed on 30 Oct 2025

President Hotel
South Beach
Price was €1,421, price is now €949 per person
€949
per person
7 Dec - 14 Dec
found 1 day ago
Return direct flight included
Warsaw (WAW) to Miami (MIA)
8.4/10 Very Good! (1,905 reviews)
The staff is very helpful with information specially Henry and the lady who works at the same desk when he is off duty. Even the guy who is parking cars offered a usufull information about the area.
Reviewed on 29 Oct 2025
Top hotels in Upper Matecumbe Key

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €252 per night from 20 Nov to 21 Nov
€252
20 Nov - 21 Nov
includes taxes & fees
9/10 Wonderful! (1,258 reviews)
A few problems with the room, ex. Coffee maker, sink in bathroom, shower, but over all excelent
Reviewed on 27 Oct 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €208 per night from 30 Nov to 1 Dec
€208
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (1,270 reviews)
We enjoyed our stay a beautiful place, but there was no free breakfast
Reviewed on 24 Oct 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €168 per night from 4 Nov to 5 Nov
€168
4 Nov - 5 Nov
includes taxes & fees
9.2/10 Wonderful! (1,548 reviews)
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.
Reviewed on 27 Oct 2025
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.
Popular places to visit
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 relaxing area.
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