Upper Matecumbe Key Travel Guide

Tourist Guide

Islamorada showing a beach bar
Islamorada which includes a beach
Islamorada
Islamorada showing mangroves, a marina and general coastal views
Islamorada showing a sandy beach, tropical scenes 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 ฿6,445 per night from 3 Aug to 4 Aug
฿6,445
฿9,437 total
3 Aug - 4 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! (1,140 reviews)
"Great chill location."

Reviewed on 24 Jul 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is ฿6,123 per night from 4 Aug to 5 Aug
฿6,123
฿8,710 total
4 Aug - 5 Aug
includes taxes & fees
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their ...
9/10 Wonderful! (1,492 reviews)
"We just got bk from 3 nts here: 2adults 1 child. We absolutely loved this hotel, it was clean, the staff were friendly and the rooms were very clean and the AC was perfect for escaping from the Florida heat and humidity. The breakfast offerings were plentiful, huge shout out to the chef for his waffles ..."

Reviewed on 25 Jul 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is ฿6,737 per night from 11 Aug to 12 Aug
฿6,737
฿9,765 total
11 Aug - 12 Aug
includes taxes & fees
Stay at this 4-star beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their ...
9/10 Wonderful! (1,016 reviews)
"10 out of 10 would recommend staying at the Islander Resort. So many fun activities and food was good. No need to leave resort because they have everything!"

Reviewed on 24 Jul 2025

Islander Resort
See all 2,735 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
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.6/10 Excellent! (494 reviews)
"Great Property, easy check in and"

Reviewed on 23 Jul 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 Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (64 reviews)
"Amazing stay, can’t wait to stay there again!"

Reviewed on 25 Jul 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 Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (90 reviews)
"Very cute bost houses. Clean and quiet."

Reviewed on 23 Jul 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 which includes 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 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

Cities near Upper Matecumbe Key

Islamorada showing a beach and tropical scenes

Islamorada