Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €208 per night from 7 Sept to 8 Sept
€208
7 Sept - 8 Sept
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is €195 per night from 17 Aug to 18 Aug
€195
17 Aug - 18 Aug
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,745 reviews)
"Very nice staff. Room was clean. Property had some nice things but the pool was not clean at all and the jacuzzi did not work."
Reviewed on 14 Aug 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is €227 per night from 19 Aug to 20 Aug
€227
19 Aug - 20 Aug
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,281 reviews)
"Always a good time!"
Reviewed on 14 Aug 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.
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (726 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
Reviewed on 14 Aug 2026
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
10/10 Exceptional! (67 reviews)
"Absolutely amazing rental! The location is incredible, we loved being able to walk to so many shops and restaurants! Publix is right around the corner! The pool gets just the right amount of shade and sun! We have already rebooked!!"
Reviewed on 4 Aug 2026
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
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.
Stay near popular Upper Matecumbe Key attractions
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