Upper Matecumbe Key

Travel Guide

Islamorada showing a beach bar
Islamorada which includes a sandy beach
Islamorada
Islamorada showing mangroves, a marina and general coastal views
Islamorada showing 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
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (1,475 reviews)
"An absolute dream! This place is absolutely amazing. Price point was great too. I can’t wait to come back!"

Reviewed on 24 Jun, 2025

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Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is S$343 per night from 6 Jul to 7 Jul
S$343
6 Jul - 7 Jul
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,222 reviews)
"The property was very nicely landscaped and the pool and beach areas had comfortable furniture and were very inviting. The chickee huts provided nice shade. There is a seawall on the beach that separates the sand and water areas. There were pretty fire pits and music in the courtyard area which also ..."

Reviewed on 23 Jun, 2025

Amara Cay Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is S$286 per night from 6 Jul to 7 Jul
S$286
6 Jul - 7 Jul
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 ...
9/10 Wonderful! (1,113 reviews)
"I was very impressed with this hotel. It’s a beautiful property and is way more lush than I had imagined. The service was top notch as well. Next time I will book for a much longer stay."

Reviewed on 23 Jun, 2025

Cheeca Lodge & Spa
See all 2,718 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! (488 reviews)
"Our stay was pleasant. The staff is friendly. The property is an older property but fairly well maintained. Our unit was updated and clean. The only complaint I have is the hot water in the shower wouldn't hold steady."

Reviewed on 28 May, 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! (61 reviews)
"Great property. Very comfortable and luxurious. The bar and food options can delivered to the room and very tasty! Really enjoyed the stay. Charlene was a great bartender by the pool!"

Reviewed on 4 May, 2025

The Islands of Islamorada
Treasure Harbor
Treasure Harbor
3 out of 5
200 Treasure Harbor Dr, Islamorada, FL
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (81 reviews)
"Very clean and great atmosphere"

Reviewed on 8 Jun, 2025

Treasure Harbor
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

3/5(2 reviews)

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

4.5/5(3 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 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
Islamorada which includes a beach and tropical scenes

Islamorada