Hotel in Upper Matecumbe Key, FL
3-Star Hotel
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this hotel
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.
A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.
This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.
A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.
Children under 16 years old are not allowed in the swimming pool without adult supervision.
The recreational activities listed below are available either on site or nearby; fees may apply.
Amenities
Air conditioning
Pool
Non-smoking
TV
Coffee/tea maker
Bar
WiFi/Internet
Microwave
Ironing facilities
Towels
Hairdryer
Map of Upper Matecumbe Key, FL
Available Rooms
Ratings and reviews
8 / 10Excellent·Jun 2026
Breakfast selection each day was excellent. Room was clean, just a little noisy from upstairs kids footsteps in the morning. 2 pools were great although main pool in need of resurfacing and a bit too warm, understandable due to 90+ temps. Love the free kayaks and paddle boards. Staff was very friendly and accommodating. Beautiful views and convenient location.
10 / 10Outstanding·Jun 2026
Great hotel on Islamorada close to everything; lots of restaurants, near to Publix, property is nice and the staff extra nice/ Shut out to Kathy on the breakfast lounge she was extra helpful. Only bad thing was the beach area was full of sargasso and we couldn't use it but that's nature's fault. you can literally walk to some restaurants and there a lot of things to do in the Key.
10 / 10Outstanding·Jun 2026
Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here.
5 / 10·Sep 2026
Such a quiet relaxing place! We loved our stay
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Top rated by guests
9Outstanding
(1,730 Ratings)
"Great hotel on Islamorada close to everything; lots of restaurants, near to Publix, property is nice and the staff extra nice/ Shut out to Kathy on the breakfast lounge she was extra helpful. Only ba..."
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