Lower Matecumbe Key

Name: Caloosa Cove Resort by CoolVacay
Rating: 9

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.

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.

Visit Lower Matecumbe Key

Matecumbe Resort

76261 Overseas Hwy Islamorada FL

S$193

15 Oct - 16 Oct

includes taxes & fees

Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, free parking and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key Historic ...

Caloosa Cove Resort by CoolVacay

73801 Overseas Hwy Islamorada FL

Stay at this condo in Islamorada. Enjoy free Wi-Fi, free parking and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.

9/10 Wonderful! (16 reviews)

"Great room and property amenities. Every room has a spectacular ocean view. Pool was awesome with plenty of chairs around it. Restaurants were very good."

Reviewed on 12 Oct, 2026

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Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

S$335

19 Oct - 20 Oct

includes taxes & fees

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 in their ...

See all 2,002 properties in Lower Matecumbe Key

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

73801 Overseas Hwy Islamorada FL

Stay at this condo in Islamorada. Enjoy free Wi-Fi, free parking and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.

9/10 Wonderful! (16 reviews)

"Great room and property amenities. Every room has a spectacular ocean view. Pool was awesome with plenty of chairs around it. Restaurants were very good."

Reviewed on 12 Oct, 2026

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...

9/10 Wonderful! (767 reviews)

"Clean and spacious. Good location for what I wanted. Loved the mini kitchen inside."

Reviewed on 12 Oct, 2026

Treasure Harbor

200 Treasure Harbor Dr Islamorada FL

Stay at this houseboat in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...

9/10 Wonderful! (178 reviews)

"They bent over backwards for us, we enjoyed the stay. Everyone should try it."

Reviewed on 10 Oct, 2026

See all properties in Lower Matecumbe Key

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.