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.
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
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Oct 29 to Oct 30
CA $202
CA $228 total
Oct 29 - Oct 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 ...
9/10 Wonderful! (181 reviews)
"Construction went on till 8 at night"

Reviewed on Oct 27, 2026

Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $227 per night from Nov 1 to Nov 2
CA $227
CA $358 total
Nov 1 - Nov 2
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
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
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! (60 reviews)
"We enjoyed our stay Elizabeth was very responsive"

Reviewed on Oct 27, 2026

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