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.
9/10 Wonderful! (11 reviews)
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Reviewed on 23 Aug 2026

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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 RM520 per night from 20 Sept to 21 Sept
RM520
RM585 total
20 Sept - 21 Sept
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 ...
9/10 Wonderful! (160 reviews)
"Nice area. Be ready for the sidewalks to roll up at 4pm."

Reviewed on 31 Aug 2026

Matecumbe Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is RM602 per night from 15 Sept to 16 Sept
RM602
RM973 total
15 Sept - 16 Sept
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 ...
9.2/10 Wonderful! (1,433 reviews)
"You don’t really expect resort food to be good but all of the restaurants on this property were excellent. The sushi spot is a 10 out of 10."

Reviewed on 4 Sept 2026

Cheeca Lodge & Spa
See all 2,074 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.
9/10 Wonderful! (11 reviews)
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Reviewed on 23 Aug 2026

Caloosa Cove Resort by CoolVacay
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
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 ...
8.8/10 Excellent! (740 reviews)
"Loved it. My husband and I stayed one night and its was ideal."

Reviewed on 5 Sept 2026

Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
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! (173 reviews)
"Ok"

Reviewed on 31 Aug 2026

Treasure Harbor
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.
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