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
Island luxury overlooking Sunset Pier, just steps from Duval Street The Westin Key West Resort & Marina sits at the heart of Old Town Key West near the famous Sunset Pier at Mallory Square, and just a block from Duval Street. Guests of the Westin Key West Resort & Marina can step out the front door to stroll... More
Downtown luxury hotel with spa, water sports and event spaceThe Hyatt Key West Resort and Spa underwent a $10-million-dollar renovation, which included updates to all 118 guestrooms. The resort reflects old-world flair combined with modern amenities, along with impeccable service and a premier location on Front Street... More
Immaculate rooms, and suites with kitchens overlook the Gulf of Mexico The Key West Marriott Beachside Hotel sits on seven lush acres of waterfront property on the east end of Key West and features a private beach. Located at the entrance to the island, the Key West Marriott Beachside Hotel offers access to the nearby... More
Newly expanded hotel with beach and oceanfront guestroomsThe newly expanded, updated Southernmost on the Beach hotel stretches along a secluded section of Key West coastline, far enough to provide respite from downtown craziness, but close enough to hit the scene any time. Guests can catch some rays on the private beach... More
Casa Marina Resort - Waldorf Astoria Collection
Key West, Florida
Best of Waldorf - Includes hotel credit
Historic beachfront luxury resort on the south side of Key WestBuilt in 1920, the Casa Marina Resort holds a spot on the National Register of Historic Places. The iconic hotel offers an ideal mix of laid-back elegance, old-Key West ambiance and modern luxury. Nestled on the island's southern edge, the resort occupies the... More
The Reach Resort - Waldorf Astoria Collection
Key West, Florida
Best of Waldorf - Includes hotel credit
Luxury resort, on-site water sports along Key West's only natural beachThe Reach Resort underwent a major renovation and now features sumptuous accommodations and abundant amenities on the island's only natural beach. Located at the end of Simonton Street just east of the Southernmost Point Marker, Reach Resort sits a... More
Lavishly equipped suites in a tropical garden setting near Old Town The Santa Maria Suites Resort sits just steps from the beach near the southern end of Duval Street. Located on the quiet, south side of the island, the Santa Maria Suites Resort offers a secluded getaway with lush gardens and extravagant suites.... More
Courtyard by Marriott Key West Waterfront
Key West, Florida
Rate includes breakfast
Get FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features spacious guest rooms and suites. It features a... More
Quiet, beachfront hotel offers abundant amenities on Key WestThe Southernmost Hotel sits at the south end of Duval Street near Key West's famous Southernmost Point of the United States. And while Southernmost Hotel is slightly removed from the hustle of the main tourist strip, it is still close enough for guests to join... More
Waterfront luxury just steps from Duval Street and Mallory SquareLocated at the northern end of Duval Street, the Pier House Resort and Caribbean Spa treats guests to Gulf of Mexico views and a location in the island's lively tourist district near Mallory Square. A waterfront fixture for nearly 40 years, the resort... More
Best in Stay
LGBT Best in Stay Key West hotels
Quiet, beachfront hotel offers abundant amenities on Key WestThe Southernmost Hotel sits at the south end of Duval Street near Key West's famous Southernmost Point of the United States. And while Southernmost Hotel is slightly removed from the hustle of the main tourist strip, it is still close enough for guests to join... More
Casa Marina Resort - Waldorf Astoria Collection
Key West, Florida
Best of Waldorf - Includes hotel credit
Historic beachfront luxury resort on the south side of Key WestBuilt in 1920, the Casa Marina Resort holds a spot on the National Register of Historic Places. The iconic hotel offers an ideal mix of laid-back elegance, old-Key West ambiance and modern luxury. Nestled on the island's southern edge, the resort occupies the... More
Lavishly equipped suites in a tropical garden setting near Old Town The Santa Maria Suites Resort sits just steps from the beach near the southern end of Duval Street. Located on the quiet, south side of the island, the Santa Maria Suites Resort offers a secluded getaway with lush gardens and extravagant suites.... More
Waterfront luxury just steps from Duval Street and Mallory SquareLocated at the northern end of Duval Street, the Pier House Resort and Caribbean Spa treats guests to Gulf of Mexico views and a location in the island's lively tourist district near Mallory Square. A waterfront fixture for nearly 40 years, the resort... More
Downtown luxury hotel with spa, water sports and event spaceThe Hyatt Key West Resort and Spa underwent a $10-million-dollar renovation, which included updates to all 118 guestrooms. The resort reflects old-world flair combined with modern amenities, along with impeccable service and a premier location on Front Street... More
Newly expanded hotel with beach and oceanfront guestroomsThe newly expanded, updated Southernmost on the Beach hotel stretches along a secluded section of Key West coastline, far enough to provide respite from downtown craziness, but close enough to hit the scene any time. Guests can catch some rays on the private beach... More
Landmark downtown hotel with excellent views of Old Town Key WestCrowne Plaza Hotel Key West - La Concha sits at an enviable Old-Town location, on Duval Street at the heart of the island's eclectic dining, shopping and nightlife. This landmark hotel, built in 1926, offers modern amenities like free high-speed Internet... More
Flights
| Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|
| Boston | Key West | Tue, May 28 - Tue, Jun 4 | $428 |
| Chicago | Key West | Wed, Jun 19 - Tue, Jun 25 | $476 |
| Philadelphia | Key West | Mon, Jun 10 - Mon, Jun 17 | $430 |
| New York | Key West | Tue, Jun 4 - Tue, Jun 11 | $400 |
| Newark | Key West | Mon, Jun 17 - Thu, Jun 20 | $432 |
| Detroit | Key West | Wed, Jun 19 - Mon, Jul 1 | $454 |
| Washington DC | Key West | Fri, Jun 14 - Wed, Jun 19 | $376 |
| Nashville | Key West | Mon, Jul 1 - Fri, Jul 5 | $445 |
| Hartford | Key West | Sat, Jun 8 - Tue, Jun 11 | $404 |
| Baltimore | Key West | Tue, Jul 9 - Tue, Jul 16 | $420 |
| Atlanta | Key West | Wed, Jul 3 - Tue, Jul 9 | $486 |
| Minneapolis | Key West | Tue, Jul 2 - Tue, Jul 9 | $464 |
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.
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- 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.
