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 $235

The Westin Key West Resort & Marina

4 stars
4.1 / 5 70 reviews

Key West, Florida

Save 25% on your stay

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
4.3 / 5 108 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 $209

Key West Marriott Beachside Hotel

4 stars
4.1 / 5 88 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 $204

Southernmost on the Beach

5 stars
4.5 / 5 120 reviews

Key West, Florida

Stay and Save Up To 10%

The brand new and renewed Southernmost on the Beach, in historic old town, stretches out on a secluded section of the island, away from the hustle of Key West activities, but close enough to the excitement when you want it. The Southernmost on the Beach hotel's private beach and pier offer front row seats to the Atlantic... More

From $239

Casa Marina Resort - Waldorf Astoria Collection

5 stars
4.2 / 5 214 reviews

Key West, Florida

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 $239

The Reach Resort - Waldorf Astoria Collection

4 stars
4.0 / 5 219 reviews

Key West, Florida

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 $291

Santa Maria Suites Resort

4 stars
4.6 / 5 36 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 $169

Courtyard by Marriott Key West Waterfront

3 stars
4.2 / 5 34 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 $139

Southernmost Hotel

5 stars
4.3 / 5 173 reviews

Key West, Florida

Stay and Save Up To 10%

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

From $252

Pier House Resort and Caribbean Spa

5 stars
4.4 / 5 118 reviews

Key West, Florida

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

Back to menu Return to top

Best in Stay

LGBT Best in Stay Key West hotels

From $139

Southernmost Hotel

5 stars
4.3 / 5 173 reviews

Key West, Florida

Stay and Save Up To 10%

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

From $239

Casa Marina Resort - Waldorf Astoria Collection

5 stars
4.2 / 5 214 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 $291

Santa Maria Suites Resort

4 stars
4.6 / 5 36 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 $252

Pier House Resort and Caribbean Spa

5 stars
4.4 / 5 118 reviews

Key West, Florida

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

From $249

Hyatt Key West Resort and Spa

5 stars
4.3 / 5 108 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 $204

Southernmost on the Beach

5 stars
4.5 / 5 120 reviews

Key West, Florida

Stay and Save Up To 10%

The brand new and renewed Southernmost on the Beach, in historic old town, stretches out on a secluded section of the island, away from the hustle of Key West activities, but close enough to the excitement when you want it. The Southernmost on the Beach hotel's private beach and pier offer front row seats to the Atlantic... More

From $209

Crowne Plaza KEY WEST-LA CONCHA

3 stars
4.0 / 5 147 reviews

Key West, Florida

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

Back to menu Return to top

Flights
Departure Arrival Travel dates Round-trip
Boston Key West Mon, Nov 17 - Thu, Dec 4 $419
Chicago Key West Fri, Nov 28 - Tue, Dec 2 $434
Philadelphia Key West Mon, Nov 24 - Thu, Dec 4 $407
New York Key West Mon, Nov 24 - Fri, Dec 5 $398
Newark Key West Mon, Nov 3 - Mon, Nov 10 $430
Detroit Key West Wed, Nov 19 - Mon, Nov 24 $501
Washington DC Key West Tue, Dec 2 - Wed, Dec 3 $376
Nashville Key West Mon, Nov 3 - Thu, Nov 6 $512
Hartford Key West Sun, Oct 26 - Sun, Nov 2 Check rates
Baltimore Key West Fri, Dec 12 - Fri, Dec 19 $460
Atlanta Key West Fri, Dec 5 - Thu, Dec 11 $478
Minneapolis Key West Tue, Dec 2 - Tue, Dec 16 $414
Back to menu Return to top

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.
    • 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

  • 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

  • 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.

Your trip

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
Age categories
Ages of children at time of trip (for pricing, discounts)