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.
9/10 Wonderful! (18 reviews)
"The hotel es wonderful very clear, The staff were very attentive, the facilities were brand new, and it was a very peaceful place. We live in a very hectic city, and it completely relaxed us. We stayed for a weekend and didn't want to leave; we plan to return."

Reviewed on Oct 27, 2026

Caloosa Cove Resort by CoolVacay
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
The price is ₩210,102 per night from Nov 8 to Nov 9
₩210,102
₩236,364 total
Nov 8 - Nov 9
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 ...
9/10 Wonderful! (182 reviews)
"The room was very clean and had a park area that if traveling with little ones will enjoy."

Reviewed on Nov 1, 2026

Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is ₩241,851 per night from Nov 29 to Nov 30
₩241,851
₩369,636 total
Nov 29 - Nov 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 ...
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.
9/10 Wonderful! (18 reviews)
"The hotel es wonderful very clear, The staff were very attentive, the facilities were brand new, and it was a very peaceful place. We live in a very hectic city, and it completely relaxed us. We stayed for a weekend and didn't want to leave; we plan to return."

Reviewed on Oct 27, 2026

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 ...
9/10 Wonderful! (777 reviews)
"Right on the ocean. Beautiful views. Very relaxing. Not busy this time of year and it was great."

Reviewed on Oct 22, 2026

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! (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

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.

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