Key West Gay Resorts and Hotels Guide

For decades, the legendary resort town of Key West, at the very southern tip of Florida, has been a magnet with gay and lesbian travelers, many who have ultimately decided to live here. Warm both in climate and personality, funky Key West draws LGBT vacationers year-round (though is especially popular as a gay spring break getaway). You'll find a wide selection of gay-friendly accommodations in town, from gay-owned, clothing-optional places geared to gay men to mixed, mainstream B&Bs, chain hotels, and resorts. Here are some of the best hotels and gay resorts in Key West.

  • 01 of 08
    Alexander's Guesthouse
    ••• Courtesy of Alexander's Guesthouse

    A beautifully designed and immaculate LGBT resort, Alexander's (1118 Fleming St., 305-294-9919) stands out for its extremely friendly and welcoming staff, lovely grounds, and the fact that it's the only gay resort in town that's caters to a true mix of women and men. For many repeat guests, that's the reason they love staying here. Amenities include several decks for sunning, some of them clothing-optional, free Wi-Fi, a nice little book and DVD library, and a cute pool with a Jacuzzi. The staff are great about helping guests plan things to see and do around Key West, and rates include a very nice breakfast as well as poolside happy hour at the resort's little cocktail spot, the Pink Monkey Bar. The upscale rooms are reasonably priced by Key West standards and include 15 standard rooms, a larger suite, and a full apartment that sleeps up to four - perfect for groups of friends. All have microwave and mini-fridge, queen or king bed, private bath, flat-screen TV, and...MORE tasteful island-inspired furnishings; some have private balconies, too. Really a terrific property from top to bottom.

  • 02 of 08
    Cypress House
    ••• Courtesy of Historic Key West Inns

    This centrally located Old Town property just a short walk from lower Duval Street, Mallory Square, and Key West Harbor is a highly popular choice among GLBT visitors - much of the staff at Cypress House (601 Caroline St., 305-294-6969) is gay, although the clientele is totally mixed, and the grounds are not clothing-optional. The inn is made up of a striking, historic 1890s "conch mansion" along with a couple of neighboring Bahamian-style conch houses, all of which access peaceful main grounds that include a lengthy lap pool, landscaped sunning area, kitchen (where Continental breakfast is served each morning), and several common areas. Rooms are moderately priced, filled with a mix vintage furnishings that capture Key West's personality and stylish contemporary pieces (including very modern bedding), and also outfitted with modern amenities like Wi-Fi, flat-screen TVs, and well-outfitted bathrooms. Many rooms have private balconies or access to decks or common balconies....MORE It's part of the Historic Key West Inns collection, which includes five other excellent, gay-welcoming properties: Albury Court Hotel, Lighthouse Court Hotel, Chelsea House Pool & Gardens, Key Lime Inn, and Merlin Guesthouse.

  • 03 of 08
    Equator Resort
    ••• © Andrew Collins

    A very popular fixture among the several gay inns along historic Fleming Street since the mid-1990s, Equator Resort (818 Fleming St., 305-294-7775) is operated by a helpful, friendly crew; has a good mix of rooms types (from standard queens to full king suites with separate sitting rooms); and makes the most of its relatively compact common spaces. All in all, it's a reliably inviting, immaculately kept, clothing-optional men's resort that's as worthy as choice for travelers mostly keeping to themselves as it is with social butterflies. If you're among the former, request a room near the front of the building. If looking more to get to know your guests, one of the rooms near the upper-level sundeck or small but attractive ground-floor pool is a good bet (by the pool there's also a sunken Jacuzzi, and additional, lushly landscaped space to laze in the sun, as well as a small bar). All rooms are tastefully appointed with tile floors, tasteful Island-inspired...MORE furnishings, flat-screen TVs (with 6 adult channels), robes, refrigerators and microwaves, irons and boards, free Wi-Fi, and plenty of other creature comforts. Continental breakfast and happy hours drinks and snacks are included in the rates.

  • 04 of 08
    Hyatt Centric Key West Resort and Spa
    ••• Courtesy of Hyatt

    The Hyatt Key West Resort and Spa (601 Front St., 305-809-1234) is one of the loveliest of Old Town's mainstream properties. With its Caribbean colonial-style buildings with balconies and tall windows, this 118-room boutique resort doesn't feel at all overwhelming or cookie-cutter, as some chain properties do. And it's a perfect choice if you'd prefer an upscale hotel experience that has a bit more in the way of facilities and amenities than many guest houses - and if you'd rather the anonymity of a larger (thought still relatively intimate) property. Rooms are spacious and bright, and each has a balcony. There's a terrific full-service spa on-site, Jala, and SHOR American Seafood Grill is a well-respected dining option, as is the laid-back Blue Mojito Bar and Grill. Also note the first-rate gym, large heated pool, and the proximity to Key West Harbor and its many outfitters for diving, snorkeling, and fishing trips.

    Continue to 5 of 8 below.
  • 05 of 08
    Island House
    ••• Courtesy of Island House

    For years it endured a somewhat shady reputation, but thanks to new management that has done a brilliant job rehabbing it, the beautiful Island House (1129 Fleming St., 305-294-6284) is "infamous" these days only because it remains a fun and lively spot for guys to meet one another, platonically or otherwise. This upscale property (rates start around $150 in high season for a basic room with a shared bath but can run quite a bit higher for the spacious pool-side suites) has a broad mix of rooms. Most are on the deluxe side, meaning large seating areas, balconies, and direct pool access, but even the simplest ones have are nicely furnished. There's a large, helpful staff at Island House, and lots and lots of social amenities - the pool, Jacuzzi, and cafe and bar serving very good food (and overlooking the pool), a health club with a five-man shower, steam room, and sauna (and yes, guys find all sorts of ways to burn off calories in here), and more. Day passes and night...MORE passes are available, by the way, for the health club and grounds - all amenities are gratis to overnight guests of the resort. The Island House is at the end of Fleming Street in the heart of the town's Historic District, a 10-minute walk from Duval Street gay bars and restaurants, and just a few blocks down from most of the other gay resorts.

  • 06 of 08
    Hotel at La Te Da Key West
    ••• © Andrew Collins

    Plenty of nonguests of the hotel regularly stop by the cheerful, handsomely designed, and centrally located La Te Da Key West (1125 Duval St., 305-296-6706), which in addition to having beautiful, upscale accommodations also contains myriad bar and dining options, including a cabaret theater, piano bar, and full-service restaurant. The adults-only property is not clothing-optional but definitely does cultivate a grown-up vibe and is a favorite of gays and straights, primarily couples. Top rooms have such high-end flourishes as marble baths, vaulted ceilings, sitting areas, and polished hardwood floors; all have refrigerators, a/c and ceiling fans, Wi-Fi, and clock radios. The most economical rooms are definitely compact but also attractively furnished and still with private baths - they're a fantastic deal compared with other hotels in this part of town. Grounds include a large pool and sundecks, and the staff here are consistently friendly and helpful.

  • 07 of 08
    Mermaid & The Alligator
    ••• Courtesy of Mermaid & The Alligator

    The whimsically named Mermaid & The Alligator (729 Truman Ave., 305-294-1894) is one Key West's classiest, most elegant accommodations. Innkeepers Dean Carlson and Paul Hayes, along with their capable staff, have worked hard to create a beautiful property that's both sophisticated and unpretentious, and that while highly popular with GLBT visitors is welcoming of all visitors - the very friendly dogs who on property also assist in making guests feel right at home. Verdant, gorgeously landscaped gardens and soaring palm trees surround the restored 1904 mansion, in which six rooms are located, as well as classic 1880s cigar-maker's cottage that contains three rooms (two of which are ideal for two sets of couples traveling together). There's a great deal of creativity and warmth to the decor, from the bird prints and Dade pine walls and floors in the Audubon Room, to pitched ceilings and deep soaking tub in the highly popular Treetop Suite. There's Wi-Fi as well as...MORE a guest computer with 24-hour access, a small heated pool, and a common living room with books, a TV, and other diversions. Although catering to a mixed gay/straight crowd, the inn is adults (16 and older) only, and rates include a substantial full breakfast.

  • 08 of 08
    Southernmost Beach Resort
    ••• © Andrew Collins

    Occupying the old gay-popular Atlantic Shores motel, which was demolished many years back to make way for it, the swank Southernmost Beach Resort (510 South St., 800-354-4455). contains 261 elegantly furnished rooms set throughout several buildings. It's an excellent location for being near both Duval Street dining and the beaches on the southern end of the island.