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 Wi-Fi, free parking and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
Get rates
Caloosa Cove Resort by CoolVacay
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
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 ...
9/10 Wonderful! (152 reviews)
"Recently had a family reunion at Matacumbe Resort staying in 3 different units. All three were different and unique which was fun. The pool was amazing and well maintained. The playground kept the kids busy. The boat dock area was convenient but tight."

Reviewed on 30 Jul 2026

Get rates
Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €228 per night from 18 Aug to 19 Aug
€228
18 Aug - 19 Aug
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 ...
Cheeca Lodge & Spa
See all 2,089 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

Caloosa Cove Resort by CoolVacay

3 out of 5
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.
Caloosa Cove Resort by CoolVacay
Private Beachfront Paradise

Private Beachfront Paradise

Islamorada FL
Stay at this beach holiday home in Islamorada. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Sunset Drive Beach and Anne's Beach are ...
9.6/10 Exceptional! (89 reviews)
"Was missing a bed that was pictured."

Reviewed on 27 Jul 2026

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

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

Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Robbie’s of Islamorada and Indian Key Historic ...
9.8/10 Exceptional! (55 reviews)
"Perfect property for our group . The washer - dryer was a huge plus after a day of fishing ."

Reviewed on 10 Jul 2026

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

Stay near popular Lower Matecumbe Key attractions

Anne's Beach

7.8/10 (597 reviews)
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
See properties
A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

Explore a world of travel with Expedia