
Upper Matecumbe Key Vacations from ¥181,286
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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
per person
Sep 13 - Sep 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,003 reviews)
A Perfect Stay on Ocean Drive
I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!
Reviewed on Jul 31, 2025

Park Central South Beach
South Beach
per person
Sep 13 - Sep 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
This property had just enough that someone would need but it’s also lacking a lot of amenities that other hotel facilities have. We were provided a small room that wasn’t clean upon arrival so we were upgraded to a bigger suite.
The suite was nice however, the wall plugs were loose so our chargers kept falling out of the walls. There was no smart tv so we were stuck with old shows or movies. The property also did not have elevators so we had to take the stairs each time we left. Luckily there was someone to help us bring our bags up and down.
This property holds a $300 security deposit so I think the lack of amenities should be improved. Lastly, the valet service takes 20 minutes so we missed a reservation. That fee was over $100.
Again, the property is nice if you don’t need all of the bells and whistles but I do think that there are better places to stay.
Reviewed on Aug 3, 2025


Find the Best Upper Matecumbe Key Vacation Packages
Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥24,346 per night from Sep 4 to Sep 5
¥24,346
¥37,339 total
Sep 4 - Sep 5
includes taxes & fees
9/10 Wonderful! (1,139 reviews)
"Restaurant options are great, they offer Italian, sushi, beachside dining and an American restaurant. There are also poolside versions of their regular American restaurant. The amenities are phenomenal, including pier fishing, bikes, games and various water sport activities. There are plenty of other ..."
Reviewed on Aug 2, 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥20,262 per night from Aug 5 to Aug 6
¥20,262
¥31,086 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (1,486 reviews)
"Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept"
Reviewed on Aug 3, 2025

Islander Resort
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥30,659 per night from Aug 11 to Aug 12
¥30,659
¥44,441 total
Aug 11 - Aug 12
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"This place was amazing! It definitely had a resort feel and was very clean. Even though the beaches aren't the normal tropic island beaches everthing inside the resort made you feel you were on an island. The staff was very helpful and friendly. The parking was free and right outside our room. The ..."
Reviewed on Aug 1, 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.
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