Upper Matecumbe Key Travel Guide

Tourist Guide

Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.
Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.
Cheeca Pier 🎣 🛶
Pelican posing for the camera in Islamorada, Florida, in the Florida Keys.
Islamorada in the Florida Keys

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is AU$888 per night from 24 Mar to 25 Mar
AU$888
24 Mar - 25 Mar
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (1,311 reviews)
All 3 pools were excellent. The sandy beach looking over the Atlantic Ocean was amazing and relaxing at the same time. The ladies went to the spa the men played the par 3 course, which is included in the resort fee.

Reviewed on 11 Mar 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is AU$559 per night from 24 Mar to 25 Mar
AU$559
24 Mar - 25 Mar
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,679 reviews)
little dated in the rooms but nice

Reviewed on 10 Mar 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$476 per night from 23 Mar to 24 Mar
AU$476
23 Mar - 24 Mar
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,268 reviews)
Loved the resort, we actually arrived a little earlier than the check in time but we were able to enjoy the amenities. Took the bikes for a little ride around, hang out by the pool and grab some nachos at the bar (amazing) definitely will come back on my next visit.

Reviewed on 9 Mar 2026

Amara Cay Resort
See all 2,791 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 ...
8.8/10 Excellent! (633 reviews)
Ocean view clean beautiful rooms

Reviewed on 10 Mar 2026

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.8/10 Exceptional! (72 reviews)
Phenomenal hotel, Marcel and Jackie were amazing with the kids and the activities offered. This is the first hotel where I feel there is great value in the resort fee with all that's included.

Reviewed on 9 Mar 2026

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat 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! (141 reviews)
The place was very clean and staff very nice. We got in very late and was only there that night,so other than sleeping I didn’t get much time for amenities, but everything on grounds was very clean and looked to be an amazing stay for longer stays. The tranquility of sitting on the deck was ...

Reviewed on 10 Mar 2026

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

Islamorada_BudnMarysDiveCenter_6069243-0004

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
Florida Keys Brewing Co. showing signage

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 showing heritage elements

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
Islamorada_MatecumbeUnitedMethodistChurch_553248621532652347-0004

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

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

Explore a world of travel with Expedia