Lower Matecumbe Key, FL

Travel Guide

A beach with a wooden pavilion, clear blue sky, and dense green foliage.
A pelican on a wooden dock with boats in the background.
Pelicans flying over a body of water.
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.
A wooden deck with benches overlooking a clear blue sea.
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
Stay at this condo in Islamorada. Enjoy free WiFi, free parking, and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
8.8/10 Excellent! (14 reviews)
"The fact we were never told the restaurant and bar were closed and the property was undergoing yearly renovations was just a lousy way to conduct business. We had to take Ubers all day just to get breakfast and lunch. If we were told we would have never booked. Spent a ton in rides since there is ..."

Reviewed on 2026/9/21

Caloosa Cove Resort by CoolVacay
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
The price is NT$3,973 per night from Sep 29 to Sep 30
NT$3,973
NT$4,469 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key ...
Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$4,732 per night from Sep 29 to Sep 30
NT$4,732
NT$7,645 total
Sep 29 - Sep 30
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 ...
9.2/10 Wonderful! (1,463 reviews)
"We booked this last minute traveling through the keys on our way to Key West. It was a fantastic place to stay. The staff were so friendly and helpful and the property was beautiful. Highly recommend. I hope we can come back and stay longer next time."

Reviewed on 2026/9/27

Cheeca Lodge & Spa
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.
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
Stay at this condo in Islamorada. Enjoy free WiFi, free parking, and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
8.8/10 Excellent! (14 reviews)
"The fact we were never told the restaurant and bar were closed and the property was undergoing yearly renovations was just a lousy way to conduct business. We had to take Ubers all day just to get breakfast and lunch. If we were told we would have never booked. Spent a ton in rides since there is ..."

Reviewed on 2026/9/21

Caloosa Cove Resort by CoolVacay
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
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 ...
Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
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! (175 reviews)
"Amazing location and well equipped. Loved the local vibe, didn't see a manatee but plenty of green iguanas. Property was comfortable with great AC."

Reviewed on 2026/9/9

Treasure Harbor
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 Lower Matecumbe Key attractions

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