Upper Matecumbe Key

Travel Guide

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is €194 per night from 10 Aug to 11 Aug
€194
10 Aug - 11 Aug
includes taxes & fees
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! (1,479 reviews)
Really nice
"The hotel is very well located. It was a very comfortable place and Jeff was very nice and made great omelettes in the morning"

Reviewed on 6 Aug 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is €211 per night from 14 Aug to 15 Aug
€211
14 Aug - 15 Aug
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! (1,143 reviews)
"Teh staff goes above and beyond to make your stay special. The customer service is first class."

Reviewed on 4 Aug 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is €219 per night from 1 Sept to 2 Sept
€219
1 Sept - 2 Sept
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! (1,239 reviews)
"Family vacation with kids and we had a great time."

Reviewed on 30 Jul 2025

Amara Cay Resort
See all 2,764 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! (502 reviews)
"You can’t find a more perfect spot for a stay in Islamorada. Everything about this place is an 11/10! Location, spacious and updated rooms, service… top notch!"

Reviewed on 4 Aug 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! (66 reviews)
"Beautiful property!"

Reviewed on 4 Aug 2025

The Islands of Islamorada
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Islamorada
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Keys History & Discovery Center and Islamorada ...
10/10 Exceptional! (54 reviews)
Family vaca/fishing trip
"Fabulous house! Awesome pool, fire pit, dock. My family thoroughly enjoyed every single moment here. Plenty of room for everyone. And the wild life is awesome! Manatees, tropical fish and iguanas!"

Reviewed on 21 Jun 2025

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
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 featuring outdoor art and a monument

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

Matecumbe United Methodist Church

Find out about the history of Islamorada when you spend time at Matecumbe United Methodist Church. Discover the beautiful sunsets in this family-friendly area or enjoy its fishing spots.

Matecumbe United Methodist Church
Islamorada showing a beach and tropical scenes

Islamorada