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 ₹12,223 per night from 26 Oct to 27 Oct
₹12,223
₹19,686 total
26 Oct - 27 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! (1,232 reviews)
"A perfect getaway for couples — the atmosphere truly feels like something out of an episode of The White Lotus. The staff is exceptionally friendly and attentive, ensuring a comfortable and memorable stay. The property offers a wide range of amenities and experiences, so there's really no need to ..."

Reviewed on 18 Oct 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is ₹11,104 per night from 28 Oct to 29 Oct
₹11,104
₹18,328 total
28 Oct - 29 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 their reviews. ...
8.8/10 Excellent! (1,260 reviews)
"This was our second stay there and will definitely go back. The location is great and there is plenty of well-maintained beach area to enjoy. The room was large, clean and updated. However, the view from the room left a lot to be desired. We booked a standard room so we didn't have expectations one ..."

Reviewed on 14 Oct 2025

Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is ₹10,351 per night from 22 Oct to 23 Oct
₹10,351
₹16,593 total
22 Oct - 23 Oct
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 ...
9.2/10 Wonderful! (1,550 reviews)
"We had a great experience at the Chesapeake!"

Reviewed on 19 Oct 2025

Chesapeake Beach Resort
See all 2,744 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! (545 reviews)
"The property is older, but very well maintained and renovated. The check in was wonderful. He gave us info about the room and recommended different things to do in the area. The room was very clean, updated, with an ocean view. The bed was very comfortable good morn"

Reviewed on 12 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 Wi-Fi, 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
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 ...
8.8/10 Excellent! (108 reviews)
"Brand new houseboats, very clean & comfortable, new pool area which was great to relax & have a dip. Lots of wildlife in vicinity"

Reviewed on 10 Oct 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

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

Cities near Upper Matecumbe Key

Islamorada showing a beach and tropical scenes

Islamorada