Upper Matecumbe Key Travel Guide

Tourist Guide

Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 5.231.991 ₫ per night from 4 May to 5 May
5.231.991 ₫
7.368.234 ₫ total
4 May - 5 May
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
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 7.878.949 ₫ per night from 10 May to 11 May
7.878.949 ₫
10.790.867 ₫ total
10 May - 11 May
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! (1,316 reviews)
What a fun place with lots of activities to be enjoyed including water activities, games and bikes. The staff were all so great and welcoming. Our room was a beach front bungalow with a screened in porch that was very enjoyable. There was a bug problem in our bed with small caterpillar creatures ...

Reviewed on 1 May 2026

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is 6.093.507 ₫ per night from 1 Jun to 2 Jun
6.093.507 ₫
8.634.225 ₫ total
1 Jun - 2 Jun
includes taxes & fees
Stay at this 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 reviews. ...
9.2/10 Wonderful! (1,001 reviews)
Wonderful resort. Immaculate grounds. Just a very happy place.

Reviewed on 30 Apr 2026

Islander Resort
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! (666 reviews)
Room was very clean and the bed was fantastically comfortable! Furniture was a bit out dated and not as comfortable as I would have liked. Pool was fantastic as well!

Reviewed on 26 Apr 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! (75 reviews)
The "suite" was a single room with a king and pullout sofa, there was no separation. So if you are traveling with children be aware that this is the same as a double queen at any other hotel room.

Reviewed on 30 Apr 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! (152 reviews)
Dallas was amazing and great at communicating. We loved staying in a house boat. Had everything we needed. We will definitely be back

Reviewed on 30 Apr 2026

Treasure Harbor
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.

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