Upper Matecumbe Key Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Cameron Abbott
Top hotels in Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 5.231.991 ₫ per night from 4 May to 5 May
5.231.991 ₫
7.368.234 ₫ total
4 May - 5 May
includes taxes & fees
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 7.878.949 ₫ per night from 10 May to 11 May
7.878.949 ₫
10.790.867 ₫ total
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (1,316 reviews)
What a fun place with lots of activities to be enjoyed including water activities, games and bikes. The staff were all so great and welcoming. Our room was a beach front bungalow with a screened in porch that was very enjoyable. There was a bug problem in our bed with small caterpillar creatures ...
Reviewed on 1 May 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 6.093.507 ₫ per night from 1 Jun to 2 Jun
6.093.507 ₫
8.634.225 ₫ total
1 Jun - 2 Jun
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Wonderful resort. Immaculate grounds. Just a very happy place.
Reviewed on 30 Apr 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.
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 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
You can spend an afternoon browsing the exhibits at History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.
