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 P11,468 per night from Nov 17 to Nov 18
P11,468
P17,528 total
Nov 17 - Nov 18
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 P10,156 per night from Nov 19 to Nov 20
P10,156
P14,983 total
Nov 19 - Nov 20
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. ...
9.4/10 Exceptional! (1,819 reviews)
"I loved having a balcony to sit on to view the water. It was perfect for morning coffee or an afternoon to read. The breakfast every morning was perfect, and provided healthy options like fruit and yogurt. I tried a bite of my husband’s omelette and it was excellent. All the staff was friendly and ..."

Reviewed on Nov 12, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is P10,632 per night from Nov 17 to Nov 18
P10,632
P16,586 total
Nov 17 - Nov 18
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
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 Nov 9, 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 WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (184 reviews)
"I never do reviews but felt like I had to this time. Jen was absolutely amazing. She was very helpful regarding our boat rental, was very patient and answered all our questions. Having the snorkel and fishing gear was super handy and saved us time and money. Everything was very clean. I highly recommended ..."

Reviewed on Nov 11, 2026

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 ...
10/10 Exceptional! (190 reviews)
"This place is so nice and quaint. The cabanas were wonderful! It rained most of our trip but our trip was not ruined because of the cabanas and all of the hammocks and sitting areas here. The availability of using kayaks and paddle boards were a lot of fun. The host was wonderful! She gave so many ..."

Reviewed on Nov 3, 2026

Island Bay 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.

Stay near popular Upper Matecumbe Key attractions