The Chesapeake Beach Resort is right on the water, and guests can walk directly onto the white sands of the hotel's private beach. The hotel's exterior is painted coral, and several walls are covered in seashells. Bright light from big bay windows fills the lobby, but the decor gets a little kitschy, with palm trees in every corner and faux plants. Next to the lobby is a large room that serves as a breakfast area in the morning and a meeting space later in the day.

There are tennis and shuffleboard courts, and two large rectangle-shaped heated pools, one of which overlooks the ocean. On the east side of the property is the hotel's private beach, tiki deck, fishing dock, and marina. Most of the guests are families with kids, though couples like it here too. 

Chesapeake Beach Resort sits on six-and-a-half acres of oceanfront sands and gardens halfway between Miami and Key West, in the Florida Keys. Restaurants such as Ziggie & Mad Dog's and Wahoo's Bar and Grill are located within a 10-minute walk from the property. Other eating places, such as Sportfish Grill, Shula Burger, Jaws Raw Bar, and Horizon Restaurant & Lounge, can be found within a five- to 10-minute drive of the hotel. Nearby attractions besides the beach include Theater of the Sea, the Marine Mammal Adventure Park, Fish Bowl Bowling Alley, the History of Diving Museum, and Lignumvitae Key Botanical State Park. Parking at the hotel is free, though past guests have complained that the lot floods during heavy rains. 

The room decor of the Chesapeake Beach Resort looks outdated and kitschy, with wicker and rattan furnishings, beach inspired prints and accessories, and palm-tree-laden curtains. Modern upgrades include free Wi-Fi in all the rooms, flat-screen TVs, and iPod docking stations. Several of the rooms, including a one-bedroom King Suite, have balconies with oceanfront views, while others look out on the garden. Some rooms have no views at all. Mini-fridges are standard and the Villas and Suites include full kitchens or kitchenettes. Bathrooms are basic, with tub/shower combos and single sinks. 

The hotel offers unlimited use of on-site non-motorized water equipment, which comes with its mandatory resort fee. Activities include kayaking, sailing, and boating. There are two heated pools, a hot tub, a tennis court, a shuffleboard court, and a children's playground. There's a small gift shop in the lobby that sells seashell jewelry, souvenirs, and cold drinks. Freebies include use of resort bicycles, Wi-Fi, a continental breakfast, and parking. There isn't a restaurant or bar on-site, though there are several options within walking distance.