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
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is AU$370 per night from 29 Jan to 30 Jan
AU$370
29 Jan - 30 Jan
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! (1,637 reviews)
Room was clean. Check in was fast and the staff was very friendly and welcoming.

Reviewed on 18 Jan 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is AU$616 per night from 29 Jan to 30 Jan
AU$616
29 Jan - 30 Jan
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 ...
9.2/10 Wonderful! (1,288 reviews)
For a five star hotel, the grounds should be kept up better

Reviewed on 14 Jan 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$445 per night from 29 Jan to 30 Jan
AU$445
29 Jan - 30 Jan
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! (1,264 reviews)
Beautiful grounds, very comfortable beds, provided water taxi between their 3 resorts, pool area with tiki bar very nice.

Reviewed on 17 Jan 2026

Amara Cay Resort
See all 2,815 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! (610 reviews)
Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need.

Reviewed on 18 Jan 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 ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on 25 Nov 2025

The Islands of Islamorada
New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

2 out of 5
Islamorada FL
Stay at this beach holiday home in Islamorada. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Bud n' Mary's Dive Center and Hurricane ...
10/10 Exceptional! (1 review)
Upon arrival, we were amazed at the beauty of the location of the home. Everything was in prestine condition. The pool and beach are minutes away from the back door. We experienced a plethora of restaurants on the island. The owners were wonderful to work with. We definitely will be returning.

Reviewed on 16 Oct 2025

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning
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 relaxing 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

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