Key West Gay and Lesbian Vacations

Key West Rainbow Flag

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

From $259

The Westin Key West Resort & Marina

4 stars
4.1 / 5 75 reviews

Key West, Florida

Island luxury overlooking Sunset Pier, few steps from Duval StreetThe 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 along... More

From $249

Hyatt Key West Resort and Spa

5 stars
4.4 / 5 116 reviews

Key West, Florida

Receive every 4th consecutive night free

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

From $229

Key West Marriott Beachside Hotel

4 stars
4.1 / 5 98 reviews

Key West, Florida

Rate includes breakfast

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

From $269

Southernmost on the Beach

5 stars
4.5 / 5 128 reviews

Key West, Florida

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

From $299

Casa Marina Resort - Waldorf Astoria Collection

5 stars
4.2 / 5 238 reviews

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

From $259

The Reach Resort - Waldorf Astoria Collection

4 stars
4.0 / 5 239 reviews

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

From $248

Santa Maria Suites Resort

4 stars
4.7 / 5 39 reviews

Key West, Florida

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

From $179

Courtyard by Marriott Key West Waterfront

3 stars
4.2 / 5 38 reviews

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

From $159

Southernmost Hotel

5 stars
4.3 / 5 199 reviews

Key West, Florida

The Southernmost Hotel in the USA is located in the heart of historic old town; away from the hustle of Key West activities, but close enough to the excitement when you want it. The Southernmost Hotel is just across the street from Atlantic Ocean, about half a block from the Southernmost Point in the USA, and a stones... More

From $249

Pier House Resort and Spa

5 stars
4.4 / 5 128 reviews

Key West, Florida

Waterfront luxury just steps from Duval Street and Mallory SquareLocated at the northern end of Duval Street, Pier House Resort and 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 features... More

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Best in Stay

LGBT Best in Stay Key West hotels

From $159

Southernmost Hotel

5 stars
4.3 / 5 199 reviews

Key West, Florida

The Southernmost Hotel in the USA is located in the heart of historic old town; away from the hustle of Key West activities, but close enough to the excitement when you want it. The Southernmost Hotel is just across the street from Atlantic Ocean, about half a block from the Southernmost Point in the USA, and a stones... More

From $299

Casa Marina Resort - Waldorf Astoria Collection

5 stars
4.2 / 5 238 reviews

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

From $248

Santa Maria Suites Resort

4 stars
4.7 / 5 39 reviews

Key West, Florida

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

From $249

Pier House Resort and Spa

5 stars
4.4 / 5 128 reviews

Key West, Florida

Waterfront luxury just steps from Duval Street and Mallory SquareLocated at the northern end of Duval Street, Pier House Resort and 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 features... More

From $249

Hyatt Key West Resort and Spa

5 stars
4.4 / 5 116 reviews

Key West, Florida

Receive every 4th consecutive night free

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

From $269

Southernmost on the Beach

5 stars
4.5 / 5 128 reviews

Key West, Florida

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

From $170

Crowne Plaza KEY WEST-LA CONCHA

3 stars
4.0 / 5 165 reviews

Key West, Florida

Save up to 25% off

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

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Flights

Departure Arrival Travel dates Round-trip
Boston Key West Tue, Jul 21 - Tue, Jul 28 $370
Chicago Key West Tue, Jun 23 - Mon, Jun 29 $393
Philadelphia Key West Sat, Jul 4 - Wed, Jul 8 $416
New York Key West Tue, Jul 14 - Thu, Jul 16 $340
Newark Key West Sun, Jul 5 - Wed, Jul 15 $350
Detroit Key West Tue, Jul 7 - Fri, Jul 10 $402
Washington DC Key West Mon, Jul 20 - Fri, Jul 24 $366
Nashville Key West Wed, Jun 24 - Wed, Jul 1 $460
Hartford Key West Wed, Jun 24 - Tue, Jul 7 $416
Baltimore Key West Tue, Jun 16 - Wed, Jun 24 $302
Atlanta Key West Tue, Jul 21 - Tue, Jul 28 $302
Minneapolis Key West Wed, Jul 15 - Tue, Jul 21 $418
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Why book on Orbitz?

  • 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’re proud sponsors of many LGBT charities and events, year after year.
  • 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.

  • 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.

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