Upper Matecumbe Key Travel Guide

Tourist 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 NZ$494 per night from 15 Nov to 16 Nov
NZ$494
15 Nov - 16 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 ...
9.2/10 Wonderful! (1,513 reviews)
"The room was clean and spacious. We stayed in a King suite, garden view. Staff throughout the property were friendly and accommodating. We had breakfast, lunch and dinner at the resort. Food was excellent at the pool and main restaurant. Drinks at the resort were pricey but delicious! Pool areas ..."

Reviewed on 12 Nov 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is NZ$413 per night from 15 Nov to 16 Nov
NZ$413
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. ...
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 12 Nov 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is NZ$461 per night from 15 Nov to 16 Nov
NZ$461
15 Nov - 16 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! (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 11 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.

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