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
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is €387 per night from 23 Feb to 24 Feb
€387
includes taxes & fees
23 Feb - 24 Feb
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,404 reviews)
"The hotel is in great condition, very clean and the staff is amazing! The breakfast is a game changer! There's an omelet station!!! Pools were nice and the fact we could bring our boat made it perfect. Couple restaurants close by also great!"

Reviewed on 17 Feb 2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is €426 per night from 25 Feb to 26 Feb
€426
includes taxes & fees
25 Feb - 26 Feb
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! (1,214 reviews)
"Loved Amara Cay. Did not know we had access to two other resorts. Friendly accommodating relaxing. Loved the Rum Runner water taxi ride and crew were fabulous. Highly recommend"

Reviewed on 16 Feb 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 €430 per night from 23 Feb to 24 Feb
€430
includes taxes & fees
23 Feb - 24 Feb
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! (1,034 reviews)
"The property had a great resort feel to it. Very clean, and the staff was great. Also, the no smoking rule was great - especially around the pool and beach area."

Reviewed on 16 Feb 2025

Cheeca Lodge & Spa
See all 2,771 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 ...
8.4/10 Very Good! (411 reviews)
"We had a wonderful stay at breezy palms....room was spacious and spotless, grounds were well kept and great location!"

Reviewed on 18 Feb 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 featuring outdoor art and a monument

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 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

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