Upper Matecumbe Key Travel Guide

Tourist Guide

Islamorada showing a beach bar
Islamorada featuring a beach
Islamorada
Islamorada featuring a marina, general coastal views and mangroves
Islamorada which includes tropical scenes, a sandy beach and general coastal views
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is NZ$435 per night from 28 Jan to 29 Jan
NZ$435
28 Jan - 29 Jan 2026
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. ...
9.2/10 Wonderful! (1,602 reviews)
Great little place on highway 1 in Islamorada. Renovated, clean great bathrooms, balconies, 2 heated pools and a jacuzzi, wonderful breakfast excellent and friendly staff and a welcome champagne drink 😃. Wait did i forget to mention amazing ocean views with ample beach chairs and umbrellas. They ...

Reviewed on 26 Dec 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is NZ$522 per night from 8 Jan to 9 Jan
NZ$522
8 Jan - 9 Jan 2026
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. ...
8.8/10 Excellent! (1,266 reviews)
Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special!

Reviewed on 21 Dec 2025

Amara Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NZ$627 per night from 4 Jan to 5 Jan
NZ$627
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,276 reviews)
AMAZING.

Reviewed on 21 Dec 2025

Cheeca Lodge & Spa
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 ...
8.8/10 Excellent! (591 reviews)
Clean room and huge

Reviewed on 23 Dec 2025

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on 25 Nov 2025

The Islands of Islamorada
New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

2 out of 5
Islamorada FL
Stay at this beach holiday home in Islamorada. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Bud n' Mary's Dive Center and Hurricane ...
Upon arrival, we were amazed at the beauty of the location of the home. Everything was in prestine condition. The pool and beach are minutes away from the back door. We experienced a plethora of restaurants on the island. The owners were wonderful to work with. We definitely will be returning.

Reviewed on 16 Oct 2025

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning
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.

Popular places to visit

Cities near Upper Matecumbe Key

Explore a world of travel with Expedia