Lower Matecumbe Key, FL

Travel Guide

D1TFGW Beautiful Anne's Beach in summer with deck in Lower Matecumbe Key, Florida Keys, USA
Lower Matecumbe Key
Lower Matecumbe Key
Lower Matecumbe Key
Lower Matecumbe Key
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
$224 nightly
The price is $251 total per night from Jun 29 to Jun 30
$251 total
Jun 29 - Jun 30
Total with taxes and fees
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.
9.8/10 Exceptional! (6 reviews)
"We had a great stay! The view is amazing. You are right on the water. Pool was clean and heated. A couple of restaurants you can walk too. Will probably stay here again!"

Reviewed on Jun 21, 2026

Caloosa Cove Resort by CoolVacay
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
$169 nightly
The price is $190 total per night from Jul 7 to Jul 8
$190 total
Jul 7 - Jul 8
Total with taxes and 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! (143 reviews)
"It was all good. Just wanted to relax!!"

Reviewed on Jun 17, 2026

Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$261 nightly
The price is $294 total per night from Jun 24 to Jun 25
$294 total
Jun 24 - Jun 25
Total with taxes and 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! (1,329 reviews)
"The decor was updated a bit but then dated in other areas. The balcony cushions had stains and the carpet needed to be replaced."

Reviewed on Jun 23, 2026

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.
9.8/10 Exceptional! (6 reviews)
"We had a great stay! The view is amazing. You are right on the water. Pool was clean and heated. A couple of restaurants you can walk too. Will probably stay here again!"

Reviewed on Jun 21, 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 laundry facilities. Popular attractions Robbie’s of Islamorada and Indian Key Historic ...
9.8/10 Exceptional! (52 reviews)
"Very cozy location for a small family. Community has a a boat ramp available."

Reviewed on Jun 22, 2026

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
 Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada FL
Stay at this vacation home in Islamorada. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Robbie’s of Islamorada ...
9.2/10 Wonderful! (31 reviews)
"Great location"

Reviewed on Jun 3, 2026

Bungalow #3 - 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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