The five guest rooms at the quietly luxurious Casa Thorn Bed & Breakfast (114 Palm Lane, 305/852-3996, from $69 d) is routinely booked solid, and it’s easy to understand why. Each guest room is individually decorated in a playful themed style, from the plush four-poster bed and Moorish chandelier in the Moroccan Suite to the tropical ambiance of the Tiki Hut. All of the guest rooms have Wi-Fi access, down comforters, and private patios, but the refined elegance of the Secret Garden Room—complete with its own private entrance and courtyard—is the best choice. Children under 8 aren’t allowed, but small pets are.
Families traveling with small children should check out Lookout Lodge (87770 Overseas Hwy., 305/852-3035, from $150 d), which offers a variety of guest-room configurations ranging from basic studios to two-bedroom suites. Most of the spacious—if somewhat dated—guest rooms have full kitchens; those that don’t have kitchenettes. All guest rooms have TV and central air-conditioning as well as free Wi-Fi and even free local and long-distance calling.
The basic Ocean View Inn & Sports Pub (84500 Overseas Hwy., 305/664-8052, from $149 d) is a fun and comfortable budget option. All seven of the guest rooms here are clean, bright, and equipped with mini-fridges and microwaves, and the pub is a good place to grab a greasy bite and knock back a few with the locals. The hotel is owned by two former NFL players, so it’s not that surprising that this is a preferred spot on Islamorada  to catch the football game on Sunday.
At the time of writing, Cheeca Lodge & Spa, a noteworthy luxury-minded family-oriented resort, was closed for repairs and renovations following a fire; this property has an excellent reputation for high-end travelers or those looking for a relaxing splurge.