Upper Matecumbe Key
Travel Guide





Visit Upper Matecumbe Key

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is HK$1,169 per night from 15 Sept to 16 Sept
HK$1,169
HK$1,888 total
15 Sept - 16 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 ...
9.2/10 Wonderful! (1,440 reviews)
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."
Reviewed on 14 Sept 2026

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is HK$1,185 per night from 16 Sept to 17 Sept
HK$1,185
HK$1,774 total
16 Sept - 17 Sept
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! (1,780 reviews)
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Reviewed on 13 Sept 2026

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is HK$1,212 per night from 17 Sept to 18 Sept
HK$1,212
HK$1,937 total
17 Sept - 18 Sept
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! (1,308 reviews)
"Beautiful lobby, nice outdoor area, room is clean, the elevator is a bit old though. Pool is very big, kids love it."
Reviewed on 13 Sept 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! (746 reviews)
"Have stayed here for the past 5 years which includes over 20 nights. Spacious rooms and clean. Like all the recent upgrades to the rooms."
Reviewed on 12 Sept 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 ...

Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (119 reviews)
"Beautiful home!! Had everything we needed for our 7 night stay. We will definitely be back."
Reviewed on 23 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.
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