Upper Matecumbe Key Travel Guide

Tourist Guide

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A pier extending into calm waters with a covered seating area and a sandy beach.
A pelican standing on a wooden dock.
A pier with birds perched on poles, a sign, and a bridge in the background.
A calm lake with a reflection of trees and a cloudy sky.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is AU$403 per night from 24 Aug to 25 Aug
AU$403
24 Aug - 25 Aug
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 ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is AU$322 per night from 6 Aug to 7 Aug
AU$322
6 Aug - 7 Aug
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. ...
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$387 per night from 5 Aug to 6 Aug
AU$387
5 Aug - 6 Aug
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! (1,301 reviews)
"Everyone, especially the young lady that checked us in were amazing! I forgot her name but she was so polite and very helpful. The room was perfect for us. My husband is on home therapy dialysis and the accommodations were perfect. The youn man at the bar (Marcus I think) even offered to help me ..."

Reviewed on 24 July 2026

Amara Cay Resort
See all 2,768 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! (711 reviews)
"my 2nd time staying here and i will be back for a 3rd"

Reviewed on 23 July 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! (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"

Reviewed on 13 July 2026

The Islands of Islamorada
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
10/10 Exceptional! (129 reviews)
"Amazing property!!Beautiful clean home in a great location! Deep-water dockage, pool, tiki, bait freezer, close to the restaurants, sandbar, & fishing, plenty of kitchen space to cook and eat and let's not forget our visits from our Manatee friend. Definitely memories were made never to be forgotten. ..."

Reviewed on 24 July 2026

5 bedroom - Deep Dockage & Heated Pool in Islamorada.
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.

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 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.
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