Opened in 1946, this beachfront resort is one of Islamorada's first luxury properties. The 27-acre grounds are a picturesque tangle of tall palm trees and tropical plants, with paths meandering past the pretty freeform lagoon pools. Wooden jetties on the interior lagoon area (distinct from the saltwater lagoon by the beach) are particularly charming, lined with padded loungers and umbrellas and lit up by fiery tiki torches at night. Islamorada is a prime spot for fishermen, and the resort caters to those wishing to fish with a 525-foot wooden pier on the beach, as well as unlimited use of fishing equipment. The 214 rooms are divided into three categories based on the type of view they have: grounds, lagoon, or ocean. All have private balconies, while some add outdoor soaking tubs, separate living rooms, and full kitchens.

Pelican Cove Resort & Marina is a waterfront property on a saltwater lagoon. Renovated in 2014, it feels a bit more sleek and stylish than many other local properties. Its 63 rooms are equipped with mini-fridges, coffeemakers, and private balconies (many with direct ocean views). There's a covered bar that serves light lunches and snacks, plus free daily breakfast, but no full restaurant. The lovely outdoor pool and hot tub offer views of the water, and guests can explore the bay with kayaks, water-bikes, and paddleboards. The marina and boat slips are available to guests, and fishing charters and eco-tours can be booked by hotel staff.

Located directly on the water in the Florida Keys, this hotel offers guests access to tons of water sports, including boating, fishing, diving, and kayaking. The hotel has its own boat dock and dive shop that offers full dive certification programs and refresher courses. A property-wide renovation completed in 2015 transformed what was once a typical value hotel chain into beachy-chic resort with modern rooms and facilities. Like many area beaches, Amara Cay's beach is more for boating than swimming, but it does feature thatched huts and an adults-only area, plus there is also a heated lagoon pool facing the water.

Chesapeake Beach Resort is a 65-room, mid-range hotel with a wide range of beach and outdoor activities. More of a family-friendly property than a romantic getaway, this hotel has its own private beach, and is located near plenty of restaurants and local attractions like the Windley Key Fossil Reef Geological State Park, the History of Diving Museum, and the Theater of the Sea. While the views are great and the atmosphere is laid-back, the resort has seen better days and charges a pesky resort fee.

Hidden from the Overseas Highway, La Siesta Resort and Marina is tucked away among tropical foliage and located directly on the ocean, with its own private beach (a unique feature, since most hotels in the Middle Keys don’t have beaches). The spacious pool deck has a relaxing, tropical vibe with hanging hammocks and panoramic ocean views.