Upper Matecumbe Key Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Cameron Abbott
Top hotels in Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 15.540.283 ₫ per night from 12 Apr to 13 Apr
15.540.283 ₫
19.405.114 ₫ total
12 Apr - 13 Apr
includes taxes & fees
9.2/10 Wonderful! (1,299 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window
Reviewed on 12 Mar 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 6.468.162 ₫ per night from 14 Apr to 15 Apr
6.468.162 ₫
8.755.218 ₫ total
14 Apr - 15 Apr
includes taxes & fees
9.2/10 Wonderful! (1,671 reviews)
The room we stayed in needs shelf space in the bathroom. It had nowhere to put toiletries. The room was clean and good a/c.
Reviewed on 16 Mar 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 6.902.047 ₫ per night from 26 Mar to 27 Mar
6.902.047 ₫
9.687.098 ₫ total
26 Mar - 27 Mar
includes taxes & fees
8.8/10 Excellent! (1,257 reviews)
Pool and beach area were extremely nice. The room was nice and clean, but you can tell it was an older hotel that they are working on remodeling. In some areas you could tell there was some deferred maintenance.
Reviewed on 15 Mar 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
4.5/5(3 reviews)
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.
