Key West has an abundance of charming guesthouses, with a large percentage catering to a mixed clientele -- either mixed gay and straight, or exclusively gay, with a couple catering to both male and female guests. Even the big straight hotels often have a noticeable gay clientele. Many of the guesthouses are historic structures: They're high on charm, but not always in the best shape. Some properties here, however, are meticulously maintained with manicured gardens, state-of-the-art TV/video, and wired and wireless Internet connections. While there is only one women's guesthouse (the expanded Pearl's Rainbow), women are welcome at a large number of the listed places.
Of these, Heron House Court, Alexander's and The Pier House are particularly welcoming of women who want a mixed environment. A number of properties cater exclusively or near-exclusively to men. While few offer the "very high sexual temperature" environment that is so common in Palm Springs, there is a variety of environments, appropriate for a broad range of travelers. Another option is to rent a home for your stay; www.rentkeywest.com or www.historichideaways.com offer historic properties with one to five bedrooms and private pools. Whatever your style, you'll find accommodations to match. Because the beach is not a focus here, our ratings reflect a heavy weighting for common areas, pool decks, grounds, and general ambiance. Count on spending a lot of time at the resort, but out of your room. Some properties do not offer in-room phones, and these are specifically noted.
ABOUT OUR PALM RATINGS
All ratings are based on cleanliness, management's friendliness and professionalism, the quality of furnishings and the attractiveness of setting and decor. The ratings represent our own opinions, guided by information from guests, staff, locals and other knowledgeable travel professionals.
Five palms indicates a lodging experience that ranks with the very best in the industry for quality of accommodations, furnishings, amenities and service. These accommodations should satisfy the most discerning travelers. Three palms is an average rating. These recommended properties generally offer pleasant, comfortable accommodations and the amenities expected by most travelers. Four palms indicates a step up in the level of amenities, more stylized decor and a broader array of services. Two-palm properties are a step below the average level of accommodation, more likely to have lower prices, worn furnishings, minimal service and/or less appealing decor. One-palm establishments offer very basic accommodations and the lowest acceptable standards of service, decor and amenities. They are suitable only for the least picky of frugal travelers, and recommendable only when options are very limited.
In terms of location, we have divided the town into five sections: Old Town, the heart of the shopping and entertainment district; North, the northern end -- removed, quiet and residential; Atlantic, near the Southernmost Point and the Atlantic Ocean; Gulf, near the Gulf of Mexico and the sunset; and Convenient, close to the heart of Old Town, but north of Elizabeth Street. Nowhere is more than a mile from anywhere else, but the distinction is useful for determining how close to the action you will be.
In terms of clientele, % straight describes the percentage of straight vs. gay guests. Exclusively gay resorts (EG) are followed by percentage of men vs. women. Note that in the partially straight places, this can vary 100 percent from week to week. For meals: CB=continental breakfast; ECB=expanded continental breakfast; FB=full breakfast; C=cocktail hour or hors d'oeuvres of some sort; WC=cocktails on weekends or only occasionally.
FIVE PALMS -- EXCEPTIONAL Alexander's (1118 Fleming St.; 800-654-9919 or 305-294-9919; 305-295-0357; www.alexanderskeywest.com or www.foremostgayhotels.com; $115-$365) Alexander's is a charming, high-end guesthouse in a gorgeously renovated Victorian mansion on the outskirts of Old Town. Rooms are spotless, nicely decorated and very comfortable. Gay-owned and -operated, Alexander's is increasingly popular with gay couples (both male and female) and groups of gay men and women traveling together. The pool area is pretty, and some rooms have porches that face the street. Multiple decks provide ample sun-exposure opportunities as well as lovely views of surrounding buildings and gardens, and the in-ground jacuzzi. A beautifully decorated and very private apartment is a nice choice for long stays (albeit an expensive one). Quiches and other freshly baked goods are staples of the continental breakfast; tea and lemonade are available throughout the day and a top-shelf happy hour is offered poolside. Other highly rated guesthouses often turn to Alexander's when they have to send overflow guests elsewhere. (Location: North; rooms: 17; nude sunbathing: permitted; sexual temperature: low; clientele: GM/L; meals: ECB/C)
Big Ruby's Guesthouse (409 Appelrouth Lane; 800-477-7829 or 305-296-2323, fax 305-296-0281; www.bigrubys.com or www.foremostgayhotels.com; email@example.com; $165-$549) Light, airy rooms are nicely decorated, scrupulously clean and very comfortable. Rooms in the older building are renovated and more charming but smaller. There are expansive sundecks, a gym, an in-ground Jacuzzi, and a tropical outdoor shower area. An apartment sleeps four with full kitchen. The location just off Duval Street is right in the middle of everything, but the extensive and exotic landscaping and tall fence help to create a sense of secluded tranquility even as the throngs march just steps away. Tasty, made-to-order hot breakfasts and evening cocktails by the pool encourage no-pressure socializing. Enjoy complementary dinner parties during special event weekends and a mimosa weekend brunch. The crowd seems younger and fun and always ready for cocktail hour. Many fiercely loyal guests have been returning for years, and Ruby's is often fully booked far in advance. Service is incredibly attentive and top-notch. (Location: Old Town; rooms: 22; nude sunbathing: permitted; sexual temperature: moderate; clientele: EG/90%M; meals: FB/C)
Heron House Court (formerly Fleur de Key; 412 Frances St.; 800-932-9119 or 305-296-4719; www.heronhouse.com; $109-$349) Heron House Court offers some of the nicest units in town. Extra little touches abound: lots of big plush towels, iced tea by the pool, an extensive library of books, travel guides and videos ... a formula for comfort that works. The sincerely friendly (but unobtrusive) staff provides for guests' every whim. These knowledgeable locals are also available to provide first-time visitors an excellent orientation to the island -- including its many hidden charms. The pool is small but pretty and the large spa is in a separate area. Located on the edge of Old Town, a six-block walk from the Duval Street masses ... a plus for some, a drawback for others. New owners purchased the Heron House and this property in 2005 and have spruced it up, adding a pleasant outdoor area with wicker chairs and an awning and retiling rooms. Although once exclusively gay, the guesthouse now takes an all-welcome approach. The gay clientele is mostly couples. (Location: North; rooms: 16; nude sunbathing: permitted; sexual temperature: low; clientele: mixed; meals: ECB/C)
Marquesa Hotel (600 Fleming St.; 800-869-4631 or 305-292-1919; fax 305-294-2121; www.marquesa.com; $175-$430) The finest accommodations in Key West and certainly one of the best small deluxe hotels in the South. Travel+Leisure's 2006 poll ranked it number one in Florida. Even standard rooms will take your breath away. The surroundings are elegant, but the atmosphere is relaxed. The largely gay staff remains unflappable even under busy conditions and provides refined but friendly service. The hotel has a loyal gay following, but it is possible you could be the only family there. Guests (often including families with children 12 and older) are decidedly upscale. The adjoining Café Marquesa has quickly risen to the top of the local dining scene...a great special-occasion spot. (Location: Old Town; rooms: 27; nude sunbathing: no; sexual temperature: low; clientele: 80% straight; meals: CB)
Be sure to follow Out Traveler on your favorite social platform
DON'T MISS THE OUT100 SPECIAL 3 DAY MARATHON STARTING NOVEMBER 24TH!
Journey through the year’s influential Out100 – the most iconic and long-standing celebration of LGBTQ+ icons and allies – in a 1-hour television special spotlighting the LGBTQ+ people shaping the world today.