Key West Gay and Lesbian Vacations
Your gay Key West vacation
The Conch Republic is at the end of the dramatic Overseas Highway that links the Florida Keys like a pearly necklace dangling into the Caribbean. Key West has been rebellious and ferociously unique throughout its history, and since the 1960s, it's been a tropical magnet for LGBT travelers looking for a mellow, free-for-all getaway.
Featured Hotels
LGBT-welcoming Key West hotels
The Westin Key West Resort & Marina
Hyatt Key West Resort and Spa
Key West Marriott Beachside Hotel
Southernmost on the Beach
Casa Marina Resort - Waldorf Astoria Collection
The Reach Resort - Waldorf Astoria Collection
Santa Maria Suites Resort
Courtyard by Marriott Key West Waterfront
Southernmost Hotel
Pier House Resort and Caribbean Spa
Best in Stay
LGBT Best in Stay Key West hotels
Southernmost Hotel
Casa Marina Resort - Waldorf Astoria Collection
Santa Maria Suites Resort
Pier House Resort and Caribbean Spa
Hyatt Key West Resort and Spa
Southernmost on the Beach
Crowne Plaza KEY WEST-LA CONCHA
Flights
| Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|
| Boston | Key West | Mon, Feb 4 - Fri, Feb 8 | $397 |
| Chicago | Key West | Sun, Feb 3 - Fri, Feb 8 | $415 |
| Philadelphia | Key West | Mon, Jan 28 - Mon, Feb 4 | $393 |
| New York | Key West | Sat, Mar 2 - Sat, Mar 9 | $346 |
| Newark | Key West | Tue, Feb 5 - Fri, Feb 15 | $364 |
| Detroit | Key West | Tue, Jan 22 - Wed, Jan 23 | $429 |
| Washington DC | Key West | Mon, Jan 28 - Fri, Feb 1 | $332 |
| Nashville | Key West | Mon, Feb 4 - Thu, Feb 7 | $407 |
| Hartford | Key West | Mon, Jan 21 - Wed, Jan 30 | $365 |
| Baltimore | Key West | Sun, Jan 20 - Thu, Jan 24 | $349 |
| Atlanta | Key West | Sun, Jan 13 - Tue, Jan 15 | $419 |
| Minneapolis | Key West | Mon, Jan 28 - Sun, Feb 3 | $482 |
Why book on Orbitz?
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Miss Richfield 1981 says it best in this video—not all travel sites are created equal. When you book on Orbitz, your travel dollars work harder. Here’s why:
- We’re the ONLY leading travel agency with a perfect Corporate Equality Index Score from the Human Rights Campaign, with two GLAAD Media awards to boot.
- We’re the ONLY leading travel site with filters for hotel reviews by other LGBT travelers.
- We feature the top gay-friendly accommodations, including Best in Stay hotels and gay resorts.
- We’re proud sponsors of many LGBT charities and events, year after year.
Key West highlights
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The island is a gayborhood
The heaviest concentration of homo haunts is on either side of Duval Street (the Bourbon Street of Florida) in Old Town. But gays are everywhere on the island, which feels like a huge, sunny Castro.
The party scene
Local gay hot spots band together from late February to early April to create Gay Spring Break. Other big draws are Conch Republic Independence Day in April (with a mock sea battle), the nudie Tropical Heat party weekend in August, Pride in June and Womenfest in September.
Winter wonderland
Nearly every weekend (especially in winter high season), the island is alive with street fairs, drag shows, leather parties, women's flag football tournaments, and special events for bears, nudists, bisexuals and anyone else.
Southern charm
Key West still has dozens of gay and lesbian and gay-welcoming guesthouses (many in historic plantation-style buildings with sweeping porches and clothing-optional pools), bars and businesses -- even gay history trolley tours -- that attract throngs of gay and lesbian followers to this day.
Picturesque sites
Sites worth visiting include the Harry S. Truman Little White House, where he spent much time. If you tire of the pool, head to "Liz Taylor," the gay name for queer-popular Fort Zachary Taylor Beach. And every evening, locals and visitors gather at the docks behind Mallory Square (at the westernmost end of Whitehead Street) to applaud the deep orange-red sunsets.
Insider tips for Key West gay travel
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Key West summer travel is cooler than Miami
Thanks to constant ocean breezes sweeping across the island, summer temperatures rarely go over 90 degrees, with less humidity than Miami, too.
Book early for winter
Winter is high season in Key West, when snowbirds flock to the island and many properties require a two- or three-night minimum. Prices can go through the roof.
If you have the time, drive
Flights take less than an hour on the extremely efficient small planes from Miami, but if you have time to spare, a three- to four-hour drive on the 159-mile Overseas Highway is a real experience.