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
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is AU$1,433 per night from 30 Mar to 31 Mar
AU$1,433
includes taxes & fees
30 Mar - 31 Mar
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 ...
9/10 Wonderful! (1,040 reviews)
"Love Cheeca"

Reviewed on 10 Mar. 2025

Cheeca Lodge & Spa
Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is AU$756 per night from 6 Apr to 7 Apr
AU$756
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,000 reviews)
"It would be nice to have music during the day Coffee availability would be a great idea as well Loved the property, the staff and convenience to other restaurants and shopping Highly recommend!!"

Reviewed on 8 Mar. 2025

Islander Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is AU$669 per night from 30 Mar to 31 Mar
AU$669
includes taxes & fees
30 Mar - 31 Mar
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,223 reviews)
"Great stay great staff great spot!"

Reviewed on 7 Mar. 2025

Amara Cay Resort
See all 2,770 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 ...
8.6/10 Excellent! (421 reviews)
20th Wedding Anniversary
"We visited Breezy Palms for our 20th wedding anniversary. We took advantage of the boat rental on site, had a great day on the water. Played cards on our lanai. Used the lovely pool, walked to local restaurants, and had a memorable time. Definitely will be back!"

Reviewed on 2 Mar. 2025

Breezy Palms Resort
The Islands of Islamorada
The Islands of Islamorada
4 out of 5
82779 Old Hwy, Islamorada, FL
Stay at this 4-star beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (52 reviews)
B-
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious ..."

Reviewed on 16 Feb. 2025

The Islands of Islamorada
Key Largo Cottages
Key Largo Cottages
2.5 out of 5
99306 Overseas Highway, Key Largo, FL
Book a stay at this beach apartment in Key Largo. Enjoy a private beach, free bicycles on site, and a garden. Popular attractions Jimmy Johnson's Big Chill and ...
9.4/10 Exceptional! (20 reviews)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for ..."

Reviewed on 7 Jun. 2024

Key Largo Cottages
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.

Popular places to visit

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
History of Diving Museum

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum
Hurricane Monument showing a monument and outdoor art

Hurricane Monument

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Hurricane Monument

Bud n' Mary's Dive Center

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 family-friendly area.

Bud n' Mary's Dive Center

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

MoradaWay Arts & Cultural District

You can spend time browsing the exhibits at MoradaWay Arts & Cultural District during your travels in Islamorada.

MoradaWay Arts & Cultural District