Upper Matecumbe Key, FL

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 NT$5,973 per night from Nov 16 to Nov 17
NT$5,973
NT$9,129 total
Nov 16 - Nov 17
includes taxes & 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 ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is NT$5,289 per night from Nov 15 to Nov 16
NT$5,289
NT$7,804 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is NT$5,537 per night from Nov 16 to Nov 17
NT$5,537
NT$8,639 total
Nov 16 - Nov 17
includes taxes & fees
Book a 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 ...
Amara Cay Resort
See all 2,731 properties in Upper 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.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (785 reviews)
"Rooms werent cleaned daily however the facilities were clean. Beach and pool on-site were excellent"

Reviewed on 2026/11/9

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 WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (185 reviews)
"Great experience"

Reviewed on 2026/11/13

Treasure Harbor
Island Bay Resort

Island Bay Resort

2.5 out of 5
92530 OVERSEAS HIGHWAY Tavernier FL
Book a stay at this beach aparthotel in Tavernier. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
Island Bay Resort
See all properties in Upper 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 Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
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