Hawks Cay Resort Rating: 4.5 Pearls
Hawks Cay Resort is the most kid-friendly in the Keys, and has the feel of a small village, due to its massive size and many amenities -- the property even has its own 85-slip marina. Many guests arrive by boat, as the resort is located on Duck Key, a secluded spot far from Key West's main airport. The property largely attracts families due to its many family-friendly features such as a dolphin experience, kids' club, playground, pirate ship pool, teen lounge, basketball court and multi-bedroom villas. Plus, the beach has calm waters which families with tots in tow will likely appreciate.
Cheeca Lodge & Spa Rating: 4.5 Pearls
Though the 114-room Cheeca Lodge is a decidedly romantic spot, it's also one of the most kid-friendly properties in the keys. The hotel was rebuilt after a fire gutted its main building in 2009, and now has bright, spacious rooms with tropical-luxe decor and massive bathrooms. The lush grounds are especially pretty at night, with Tiki-torch-lit paths. Family-friendly amenities include the manmade beach, the kids' club, free kayaking and bike rentals, and the private fishing pier with free fishing rod rental. Plus, many rooms have pullout sofas and some have full kitchens.
Sunset Key Guest Cottages, a Westin Resort Rating: 4.5 Pearls
This 40-room resort caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities. It is located on Sunset Key, a residential island off Key West, and is affiliated to the Westin Key West, with which it shares some features, such as the fitness center and the restaurants. The hotel itself has wonderful amenities, including a lovely pool, a gorgeous beach with palm trees and clear waters, and a pleasant spa. Its location is idyllic and exclusive, making it a nice, quiet spot for families. Families will likely enjoy the tennis courts, the spacious cottages (all with kitchens or kitchenettes), and freebies such as breakfast basket delivery, morning newspaper delivery, Wi-Fi, and library loans (books, movies, and music).
Casa Marina Resort - a Waldorf Astoria Resort Rating: 4.5 Pearls
The 311 rooms of the Casa Marina Resort have a light, sophisticated, but still island-y feel, with neutral tones, sheer curtains, and sleek hardwood or tiled floors. The resort also offers great in-room amenities, including free Wi-Fi, flat-screen TVs, and espresso machines. Although bathrooms aren't anything grand (just simple walk-in showers or shower/tub combos), they're clean and sleek. The resort's grounds are beautiful, with palm trees and lush foliage, and lead to a rare amenity in Key West -- a swimmable beach, which is a big plus for families. Although it's too rocky to wade into the water, a long dock extends to sandier bottoms. Cribs and babysitting services are also available.
Southernmost on the Beach Rating: 4.0 Pearls
Southernmost on the Beach is a Key West favorite, and though it's more popular with couples, it still draws plenty of families with its beachfront location. The hotel has lovely architectural details such as arched doorways, crown molding, bay window seats, and porthole windows. Many rooms have balconies, and some have corner, wrap-around balconies with ocean views that are truly spectacular. Polished rooms are decorated in soothing, beach-inspired tones. Highlights here include the spectacular beach, long pool, private sunbathing pier, and sunny fitness center. The hotel is located on the far end of Duval street, giving guests easy access to Key West's famous bars and restaurants without the annoyance of nighttime noise. With hammocks strung between palm trees and Adirondack chairs looking out over the ocean, this 124-room hotel provides the perfect environment to relax. Cribs can be provided upon request, but there are no babysitting services.
Marriott Key Largo Bay Beach Resort Rating: 4.0 Pearls
This 153-room property is located in northern Key Largo, a short drive from the John Pennekamp Coral Reef State Park, and close to shops and restaurants. Not a lot stands out, but there are a few perks -- like a diver's center on-site, an adequate spa, and a nice private beach (albeit a tiny one, with little room for swimming) with water sports. Big rooms have flat-screen TVs, free Wi-Fi, and nicer decor than other mid-range chains in the area -- but many bathrooms could use a renovation. Upgrading to a suite will give you a full kitchen and a large sitting area, but smaller sleeping quarters. Book a room with an ocean view to enjoy the beautiful Key Largo sunsets (and avoid facing the nearby highway).
Coral Lagoon Resort and Marina Rating: 4.0 Pearls
The Coral Lagoon Resort & Marina has 25 airy, cheerful cottage units that dwarf typical hotel rooms. They're tasteful and homey, with a tropical color palate of yellows, greens, and blues; full kitchens; porches; and high-tech amenities including flat-screen TVs with cable, DVD players, and iPod docks. Its location on Marathon makes it popular with sport fishermen, and the property's marina make it especially convenient for guests with boats. The lack of services makes it a better fit for do-it-yourself travelers, but families will appreciate the space and the decently sized pool.