Lower Matecumbe Key

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.
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
The price is CA $178 per night from Oct 21 to Oct 22
CA $178
per night
Oct 21 - Oct 22
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! (175 reviews)
"We came in late and office was closed.it took a couple calls but someone finally came. If you are looking for old Florida, this is it."

Reviewed on Oct 16, 2026

Matecumbe Resort
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! (17 reviews)
"Very clean efficiency with a full fridge, stove and oven. Grills by the water to cook your own catch or from the market down the road. Large pool, well maintained."

Reviewed on Oct 15, 2026

Caloosa Cove Resort by CoolVacay
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $236 per night from Oct 22 to Oct 23
CA $236
per night
Oct 22 - Oct 23
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! (17 reviews)
"Very clean efficiency with a full fridge, stove and oven. Grills by the water to cook your own catch or from the market down the road. Large pool, well maintained."

Reviewed on Oct 15, 2026

Caloosa Cove Resort by CoolVacay
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada FL
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Robbie’s of Islamorada and Indian Key Historic ...
9.8/10 Exceptional! (59 reviews)
"Loved this property. Recently renovated and very lovely. Super clean and great amenities. Conveniently located and comfortable."

Reviewed on Sep 13, 2026

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Islamorada FL
Book a stay at this beach vacation home in Islamorada. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Robbie’s of Islamorada and Indian ...
10/10 Exceptional! (119 reviews)
"Beautiful property! Everything was as described. We would love to book again next year!"

Reviewed on Jul 3, 2026

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
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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