Upper Matecumbe Key, FL
Travel Guide
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Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundable
The price is $284 total per night from Nov 29 to Nov 30
$284 total
per night
Nov 29 - Nov 30
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 $212 total per night from Nov 10 to Nov 11
$212 total
per night
Nov 10 - Nov 11
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! (1,807 reviews)
"Our room wasn’t really just our room. It had a door to the adjacent room so they can make it a suite. It has a huge gap under both doors so you can hear our neighbor cough,talk, and listen to the tv. You can see the light from their room shining under in our room and see shadows when they in The ..."
Reviewed on Nov 4, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is $250 total per night from Nov 16 to Nov 17
$250 total
per night
Nov 16 - Nov 17
Book a 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 ...
8.8/10 Excellent! (1,326 reviews)
"I had heard great things about this property and decided to stay here with a group of friends. We were a little disappointed when we arrived in the hallway that we were staying on was under construction. This was not disclosed at the time of our booking and when we ask The front desk about it, they ..."
Reviewed on Nov 5, 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 ...
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! (120 reviews)
"A"
Reviewed on Oct 18, 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! (180 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
Reviewed on Oct 23, 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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- Oceanic Airlines Norfolk (ORF) to Marathon (MTH) flights
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- Founders Park
- Hurricane Monument
- Bud n' Mary's Dive Center
- Florida Keys Brewing Co.
- Islamorada Brewery & Distillery
- History of Diving Museum
- Hurricane Monument
- MoradaWay Arts & Cultural District
- Matecumbe United Methodist Church
- Everglades National Park
- John Pennekamp Coral Reef State Park
- Baker's Cay Resort Beach
- Anne's Beach
- Long Key State Park
- Fiesta Key
- Jacob's Aquatic Center
- Founders Park
- Harry Harris Park
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- Sunset Drive Beach
- Alligator Reef Lighthouse
