Upper Matecumbe Key

Travel Guide

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is P8,617 per night from Aug 24 to Aug 25
P8,617
P12,903 total
Aug 24 - Aug 25
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! (1,490 reviews)
"Beautiful property"

Reviewed on Aug 10, 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 P9,071 per night from Aug 19 to Aug 20
P9,071
P14,056 total
Aug 19 - Aug 20
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! (1,141 reviews)
"Great all around!"

Reviewed on Aug 8, 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is P9,592 per night from Sep 1 to Sep 2
P9,592
P14,580 total
Sep 1 - Sep 2
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)
"The staff was very personable and accommodating.. it was our 32nd weeding anniversary and they had left a handwritten note and a treat in our room… it was appreciated… The grounds were nice and clean with the exception of the water area around the end of the property where the event area is located ..."

Reviewed on Aug 11, 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! (503 reviews)
"The property is close to other great dining, always very clean"

Reviewed on Aug 8, 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 Aug 4, 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 ...
8.8/10 Excellent! (97 reviews)
"We never slept in a houseboat before and it certainly was interesting and fun"

Reviewed on Aug 2, 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 featuring 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

Matecumbe United Methodist Church

Find out about the history of Islamorada with a stop at Matecumbe United Methodist Church. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.

Matecumbe United Methodist Church