Key West guesthouses don't usually welcome families, but this laid-back jumble of rooms and suites is an exception. If you can live with a few flaws, you'll grab a bargain. Accommodations in the 1930s Simonton House, with four-poster beds, are most suitable for couples. The one- and two-bedroom updated suites are popular with families. Bright, roomy cottages are perfect if you want a bit more privacy. Get a room in the back if you are bothered by noise. The leafy courtyard and pool area are where guests hang out day and night.