Upper Matecumbe Key

Travel Guide

A shark sculpture with a sign above it that reads "Islamorada Florida Keys".
A marina with boats docked, a motel, and a cafe.
A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A calm lake with a reflection of trees and a cloudy sky.
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €251 per night from 18 Nov to 19 Nov
€251
18 Nov - 19 Nov
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
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is €214 per night from 15 Nov to 16 Nov
€214
15 Nov - 16 Nov
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is €237 per night from 16 Nov to 17 Nov
€237
16 Nov - 17 Nov
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
Amara Cay Resort
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.
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 ...
9/10 Wonderful! (785 reviews)
"Rooms werent cleaned daily however the facilities were clean. Beach and pool on-site were excellent"

Reviewed on 9 Nov 2026

Breezy Palms Resort
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (120 reviews)
"A"

Reviewed on 18 Oct 2026

Oceanfront Private Cottage!
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! (185 reviews)
"Great experience"

Reviewed on 13 Nov 2026

Treasure Harbor
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 Upper Matecumbe Key attractions

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