
Upper Matecumbe Key Vacations
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Upper Matecumbe Key Hotel Deals

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥16,805 per night from Aug 28 to Aug 29
¥16,805
¥27,200 total
Aug 28 - Aug 29
includes taxes & fees
9/10 Wonderful! (1,499 reviews)
"Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!"
Reviewed on Aug 24, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥20,867 per night from Sep 4 to Sep 5
¥20,867
¥33,428 total
Sep 4 - Sep 5
includes taxes & fees
9/10 Wonderful! (1,157 reviews)
"Excellent place for a restful weekend"
Reviewed on Aug 23, 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥24,782 per night from Sep 1 to Sep 2
¥24,782
¥37,667 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,240 reviews)
"Beautiful and the smell is wonderful"
Reviewed on Aug 25, 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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