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
Non-smoking
Map of Upper Matecumbe Key, FL
Available Rooms
Ratings and reviews
10 / 10Outstanding·Jul 2026
Good stay
8 / 10Excellent·Jul 2026
The water was not clean, but the property was
8 / 10Excellent·Jul 2026
Everyone was very nice at the resort, rooms very clean. I wish we could swim in the ocean but it was full of seaweeds
5 / 10·Oct 2026
Lovely place to stay in Islamorada. Beach and pools were great. Fantastic breakfast included with made to order omelettes. Parking was available. We stayed in the most basic room which was in the building by the office so we could hear traffic from the Overseas Highway but was it pretty quiet inside and we had no issues at night. There is a nice seating area out back too with private balcony and two chairs. The pool and beach are steps away so very easy to access.
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Top rated by guests
9.4Outstanding
(1,791 Ratings)
"Good stay"
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