New Town / North Roosevelt Boulevard

Fairfield Inn and Suites Key West at The Keys Collection

★★★★★

Key West is one of the most expensive hotel markets in Florida, and families quickly discover that the charming Old Town guesthouses either do not take children or charge a fortune for small rooms. The Fairfield Inn and Suites at The Keys Collection is the practical answer. It sits on North Roosevelt Boulevard in New Town, the commercial side of the island near the entrance from the Overseas Highway, part of a cluster of Marriott-family hotels known as The Keys Collection. What it offers that most Old Town properties cannot is value: a complimentary hot breakfast buffet every morning, free on-site self-parking (a significant saving in Key West), and a large resort-style pool with poolside cabanas and loungers in a tropical setting. Rooms are straightforward and well kept, with double-queen options that suit families, and the hotel describes itself as family-friendly. Getting to the sights takes a little planning: Duval Street is roughly three miles away, about ten minutes by car or a longer bike ride, and the hotel's information mentions shuttle service to downtown on a reservation basis, though details vary, so confirm at the front desk. Trade-offs to know: it is a chain hotel without island character, the surroundings are a busy commercial boulevard, housekeeping is every other day, pets are not allowed, and the minimum check-in age is 21. But for families, road-trippers driving down the Keys with a car, and anyone who would rather spend their budget on boat trips and restaurants than on a room, it is one of the smartest bases in Key West.

Why stay in New Town: Old Town is wonderful, but it is small, parking is scarce and expensive, and hotel rates reflect its charm. New Town, along North and South Roosevelt Boulevards, has larger hotels with pools and parking, supermarkets and pharmacies for families, and quick access to the airport, Smathers Beach and the Key West Tropical Forest and Botanical Garden. From here, the drive or ride into Old Town is short, and many visitors split their days between the pool and town.

Making the most of it: eat the free breakfast and pack a picnic for the beach to stretch your budget. Use your car for day trips up the Keys to Bahia Honda State Park, then leave it parked when you go into Old Town and take the shuttle, a rideshare or bikes instead to avoid downtown parking costs. Reserve a cabana if you plan a pool day, and ask about the downtown shuttle schedule at check-in. Rooms facing the pool are generally quieter than those facing the boulevard. If you are arriving late after the long drive down the Overseas Highway, the free parking and easy access from the main road make check-in simple.

Who it suits: families with children, budget-conscious couples, road-trippers and groups who want reliable rooms, breakfast and parking without fuss. Travelers who want to step out of their door into historic streets, or couples seeking romance, should choose an Old Town guesthouse such as the Gardens Hotel or Eden House instead. Pair a stay with Smathers Beach and Fort East Martello nearby, and an Old Town day with the Conch Tour Train for orientation.