Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL 33036, Islamorada, United States

3-star hotel

Guest rating: 4.3 / 5

Overview

Chesapeake Beach Resort is a 3-star, oceanfront resort in Islamorada set on 6.5 acres of sand and gardens. It has a strong public reputation, rated 4.3/5 from 1,195 reviews. The property includes a harbor that accommodates boats, giving it a distinctly on-the-water Keys feel.

Rooms & Suites

Rooms and suites are colorful and designed to take advantage of the setting, with screened-in balconies that overlook either the ocean or the gardens. Standard in-room features include minifridges, free Wi-Fi, coffeemakers, and flat-screen TVs. Suites add full kitchens, pull-out sofas, and Jacuzzis, and room service is available.

Dining

A breakfast buffet is included free of charge, a highlight frequently emphasized by guests. Reviews point to a notably broad spread, including baked goods and savory options. This makes the resort appealing to travelers who prefer a ready-made start before getting on the water or heading to nearby attractions.

Amenities & Recreation

Recreation is centered around the waterfront: the resort has two heated oceanfront pools, a tennis court, and a water sports center that rents kayaks and bikes. Guests can also fish from the property or arrange charters, supported by the on-site harbor. Free parking is included, and guests mention conveniences like provided pool towels and responsive text-based help for questions.

Location & Nearby Attractions

The resort sits on Overseas Highway in Islamorada, about an 11-minute walk (approximately 898 m) from the History of Diving Museum. Other nearby points of interest include Theater of the Sea (1.35 km), Islamorada Brewery & Distillery (about 1.93 km), and the Keys History & Discovery Center (about 2.29 km). Nature and day-trip options include Windley Key Fossil Reef Geological State Park (about 3.03 km), Islamorada Sandbar (about 3.46 km), and Lignumvitae Key Botanical State Park (about 9.47 km).

Best for

This resort fits couples and leisure travelers who want an oceanfront stay with active, on-site recreation—two heated pools, kayaking and biking rentals, and fishing/charter options supported by an on-site harbor. It also suits travelers who value convenience, thanks to free parking, free breakfast, and walkable access to the History of Diving Museum. Guests who prioritize views may especially appreciate ocean-view balconies.

Travel tips

If an ocean view matters to you, consider selecting a room category with an ocean-facing balcony, as guests often single out the views. Plan at least one morning around the included breakfast buffet, which reviewers frequently describe as unusually substantial. Many major attractions in Islamorada are a short drive up and down Overseas Highway, including Theater of the Sea (about 1.35 km) and Windley Key Fossil Reef Geological State Park (about 3.03 km).

What guests say

Guests frequently praise the resort’s cleanliness and the overall beauty of the oceanfront setting, often highlighting the views. The included breakfast buffet stands out in reviews for its variety, with both sweet and savory options mentioned. Reviewers also note helpful, quick communication (including text-based responsiveness) and appreciate extras such as pool towels and access to bikes/kayaks/SUP. A small negative theme appears around occasional hiccups that management resolves quickly, and one review mentions frustration with fishing gear tangling.

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