You'll find a wide variety of places to stay in Key West, from resorts with all the amenities to seaside motels, quaint bed-and-breakfasts, and clothing-optional guesthouses. Unless you're in town during Key West's most popular holidays -- Fantasy Fest (around Halloween), where Mardi Gras meets South Florida for the NC-17 set; Hemingway Days (in July), where Papa is seemingly and eerily alive and well; and Christmas and New Year's -- or for a big fishing tournament (many are held Oct-Dec) or boat-racing tourney, you can almost always find a place to stay at the last minute. However, you may want to book early, especially in winter, when prime properties fill up and many require 2- or 3-night minimum stays. Prices at these times are extremely high. Finding a decent room for under $100 a night is a real trick.
Another suggestion, and my recommendation, is to call Vacation Key West (tel. 800/595-5397 or 305/295-9500; www.vacationkw.com), a wholesaler that offers discounts of 20% to 30% and is skilled at finding last-minute deals. It represents mostly larger hotels and motels, but can also place visitors in guesthouses. The phones are answered Monday through Friday from 9am to 6pm and Saturday from 11am to 2pm. Key West Innkeepers Association (tel. 800/492-1911 or 305/292-3600) can also help you find lodging in any price range from among its dozens of members and affiliates.
Gay travelers may want to call the Key West Business Guild (tel. 305/294-4603), which represents more than 50 guesthouses and B&Bs in town, as well as many other gay-owned businesses. Be advised that most gay guesthouses have a clothing-optional policy. One of the most elegant and popular is Big Ruby's, 409 Applerouth Lane (tel. 800/477-7829 or 305/296-2323; www.bigrubys.com), located on a little alley just off Duval Street. Rates start at $147 double in peak season and $102 off season. A low cluster of buildings surrounds a lush courtyard where a hearty breakfast is served each morning and wine is poured at dusk. The all-male guests hang out by the pool, tanning in the buff. Also popular is Oasis, 823 Fleming St. (tel. 305/296-2131; www.keywest-allmale.com), which is super-clean and friendly, with a central location and a 14-seat hot tub. Rates are $169 to $229 in winter and $109 to $169 in summer.
Another luxurious property is the Florida Key Guesthouse, 412 Frances St. (tel. 305/296-4719), which is more romantic and traditionally decorated and welcomes many lesbian travelers as well. Out and About gave it a five-star rating. Rates are $225 in season and $125 off season. For women only, Pearl's Rainbow, 525 United St. (tel. 800/74-WOMYN or 305/292-1450; www.pearlsrainbow.com), is a large, fairly well-maintained guesthouse with lots of privacy and amenities, including two pools and two hot tubs. Rates in season range from $99 to $229.
