
Lower Matecumbe Key Holidays
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Top hotels in Lower Matecumbe Key

Matecumbe Resort
76261 Overseas Hwy Islamorada FL
The price is 4.452.305 ₫ per night from 28 May to 29 May
4.452.305 ₫
5.008.843 ₫ total
28 May - 29 May
includes taxes & fees
9/10 Wonderful! (136 reviews)
"Nice property, but unfortunately located on beach that is not for swimming. Even if high tide the water was knee high at the most. And you have to cross through significant amounts of seeweed. Free kayak was a big plus."
Reviewed on 26 May 2026

Caloosa Cove Resort by CoolVacay
73801 Overseas Hwy Islamorada FL
The price is 5.121.468 ₫ per night from 31 May to 1 Jun
5.121.468 ₫
6.650.795 ₫ total
31 May - 1 Jun
includes taxes & fees

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 5.230.800 ₫ per night from 8 Jun to 9 Jun
5.230.800 ₫
7.366.555 ₫ total
8 Jun - 9 Jun
includes taxes & fees
9.2/10 Wonderful! (1,738 reviews)
"I had a wonderful time on my getaway. The view from my room was beautiful. Everything was quite and pleasant perfect for a family. Everyone was polite, and the breakfast was delicious. The view of the breakfast was phenomenal."
Reviewed on 26 May 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

Anne's Beach
4.5/5(3 reviews)
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Robbie’s of Islamorada
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
Sunset Drive Beach
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
