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Key West Gay Resorts and Hotels Guide

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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.

1. Alexander's Key West

photo by Andrew Collins
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 tasteful island-inspired furnishings; some have private balconies, too. Really a terrific property from top to bottom.

2. Big Ruby's Guesthouse

photo by Andrew Collins
Of the clothing-optional gay resorts in town, the attractive compound Big Ruby's (409 Applerouth Lane, 305-296-2323) stands out for a couple of reasons: it's just a few steps from famous Duval Street, where you'll find most of the gay bars and many of the hip restaurants and shops in town. And while it draws a predominantly male crowd, it does welcome lesbian guests, too. This beautiful landscaped property in Old Town consists of a large sunning area adjacent that's connected by a short path to a kidney-shape pool and a main building where guests check in and have complimentary breakfast each morning (as well as late-afternoon happy hour with snacks). There's also a large outdoor hot tub, and a gym. Rooms are set around the property in a few different buildings, and some on the ground floor and some a level up - they're tastefully furnished with top-quality linens, pastel-painted walls, and Key West-inspired furnishings. Some are in historic buildings with hardwood floors, some in newer buildings. There are a handful of free parking spots, too.

5. Cypress House

photo by Andrew Collins
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. 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.

7. Equator Resort

photo by 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 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.

10. Hyatt Key West Resort and Spa

photo by Andrew Collins
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.

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