At the southern end of the Eastern U. S. seaboard lies a city whose heritage seeps of a close knit gay community and thriving artistic enclave. Known now for its blend of vibrant Mardi Gras like festivals and laid-back margaritaville atmosphere, Key West prides itself on its numerous guest houses and gay friendliness par excellence.

When you visit, be sure to take a half hour out of your oh so busy day of idling on the beach and catch a trolley tour of the city. Gay tours are available, to give you a sense of the lifestyles down here. In between your stroll down the famous Duval Street or your snorkeling along the reefs, make sure you catch the four legged feline presence at Ernest Hemingway's House. But if you can catch the city while it's hosting Fantasy Fest or Women's Week, then have a blast!

Casa Marina Resort, The Waldorf Astoria Collection

Casa Marina Resort, The Waldorf Astoria Collection

If this resort's stunning Renaissance decor lures you to this luxurious resort, the beautiful and peaceful private beach will convince you that you made the right choice. During the day, explore the ocean with a rented wave runner or take advantage of the outstanding snorkeling opportunities. Take a break from the beach and play a few sets at one ... read more

Doubletree Grand Key Resort

Doubletree Grand Key Resort

Experience one of the finest resort hotels in the Florida Keys. The Grand Key Resort is a deluxe hotel that is located on the quiet side of Florida Keys near beaches and the Key West International Airport. Decorated in traditional island decor and tropical landscaping, the hotel’s elegant cottages and public areas have been designed to accommodate ... read more

Heron House

Heron House

A 23-room property comprised of three historical "Conchstyle" homes and awarded four diamonds by AAA and four crowns by the American Bed and Breakfast Association. Guestrooms are all uniquely decorated with a light, airy feel and feature small details, such as fine woodwork, tropical stained glass artistry, intricate stonework, and the elegance of ... read more

  • Complimentary Continental Breakfast daily.

    offer details

    Valid on new bookings only. Book by 4/30/2010. Travel 1/1/2009 - 4/30/2010.

Hyatt Key West Resort & Spa

Hyatt Key West Resort & Spa

Located directly on the gulf and within walking distance of prime shops and attractions, Hyatt Key West Resort and Spa is a year-round, contemporary resort on the Gulf of Mexico. Reflective of the charm and character of Key West, its 118 spacious rooms offer expansive balcony views, stylish decor, the Hyatt’s signature Grand Bed, deluxe bathrooms, ... read more

Little Palm Island Resort and Spa

Little Palm Island Resort and Spa

Little Palm Island Resort & Spa is an internationally acclaimed private island paradise that is listed among the top resorts in the world. Crushed seashell paths wind through lush gardens to thatched-roof bungalows, which serve as your guest quarters. Little Palm Island Resort & Spa has something to please each and every guest. From the natural w ... read more

Ocean Key Resort & Spa

Ocean Key Resort & Spa

Ocean Key Resort & Spa has newly renovated deluxe rooms, Jr. Suites/Caribbean Suites, all delightfully large, illuminated with the energy and colors of Key West life. There are spacious balconies opening to breathtaking views, sensual bathrooms, all flooded in tropical warmth. It's a full service resort uniquely positioned where the Gulf of Mexico ... read more

Sheraton Suites Key West

Sheraton Suites Key West

An oasis from your hectic lifestyle, the Sheraton Suites Key West is Key West’s only all-suite hotel. It’s the perfect place for you to be yourself. Take a dip in our lagoon-style pool, read a book amidst the tropical foliage, or take a stroll along Smather’s Beach, just across the street. For the outdoor enthusiast, allow our onsite concierge ... read more

Westin Key West Resort & Marina

Westin Key West Resort & Marina

This romantic Victorian-style hotel is located directly on the Gulf of Mexico in the heart of Old Town Key West. Walk to Duval Street and Mallory Square or take the ferry to the sandy private beach on Sunset Island. Amenities include pool, Jacuzzi, health club, a variety of water sports, gift shop, restaurant, lounge and room service. Golf nearby. ... read more

Exclusively Gay Icon
Indicates exclusively gay guesthouses and resorts which rate among the very best in the world.
Damron Icon
Indicates that the property is included in Damron Vacations' worldwide collection of lesbian and gay friendly hotels.