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$309 per night from 15 Oct to 16 Oct
AU$309
15 Oct - 16 Oct
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! (1,222 reviews)
"I went there this weekend to celebrate my birthday. Great place, well kept, nice service, rooms are pretty and clean. The pools are nice. Loved the resort. Hope to come back soon. They had a room for me right away. Check in was very pleasant. The paddle boarding, and canoes are free with the stay. ..."

Reviewed on 12 Oct 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is AU$334 per night from 19 Oct to 20 Oct
AU$334
19 Oct - 20 Oct
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. ...
9.2/10 Wonderful! (1,536 reviews)
"I had a wonderful stay here with my pet! The hotel is super pet-friendly, which made our trip so easy and enjoyable. There’s plenty of parking, and the view from our room was amazing. I also loved that my favorite buffet was right in the parking lot next door — total bonus! Perfect spot for anyone ..."

Reviewed on 9 Oct 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is AU$320 per night from 19 Oct to 20 Oct
AU$320
19 Oct - 20 Oct
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! (1,254 reviews)
"Room was spacious, clean with a great balcony."

Reviewed on 7 Oct 2025

Amara Cay Resort
See all 2,800 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! (543 reviews)
"The reception staff was great. The beach area had a little plastic trash on it. The room was nice."

Reviewed on 4 Oct 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! (58 reviews)
"This property was perfect for our group. It was located near all the restaurants we wanted to try and access to both the gulf and Atlantic was easy. I highly recommend this property."

Reviewed on 29 Sept 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 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 relaxing 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

After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area or enjoy its fishing spots.

Matecumbe United Methodist Church

Explore a world of travel with Expedia