Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $237 per night from Oct 22 to Oct 23
CA $237
CA $371 total
Oct 22 - Oct 23
includes taxes & fees
Book a 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 ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is CA $195 per night from Oct 18 to Oct 19
CA $195
CA $299 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.4/10 Exceptional! (1,796 reviews)
"Excellent location we had a Waterview room, which was extremely clean well maintained with a beautiful view of the ocean and beach from our balcony. Both swimming pools were well maintained. Only glitch was hot tub was not working.. would definitely stay again ."
Reviewed on Oct 16, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
The price is CA $295 per night from Oct 18 to Oct 19
CA $295
CA $436 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,143 reviews)
"Very nice experience and cosy hotel in the Keys, super recommended!"
Reviewed on Oct 16, 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
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (770 reviews)
"This property is a nice old Florida style hotel with a nice pool, a small beach and marina. The room was very clean and comfortable with a strong air conditioner. Islamorada it’s still hot in October. We got the room with ocean view and a kitchen. Is a spacious space with a pretty nice stove, lots ..."
Reviewed on Oct 16, 2026
Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free WiFi, 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 Aug 23, 2026
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (179 reviews)
"The boat was very clean and included all the amenities we needed. The air conditioning worked very well. The host was extremely accommodating with our very late check-in and early departure. I would definitely recommend!"
Reviewed on Oct 15, 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.
Stay near popular Upper Matecumbe Key attractions
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