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

Nightly rates from $239

The Westin Key West Resort & Marina

4 stars
4.2 / 5 55 reviews
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 along the waterfront promenade or experience the endless boutiques, cafes, and island bars of downtown Key West. The Westin Key West Resort & Marina also offers the largest on-site marina of any hotel on the island, and conference and event groups can find 16,000 square feet of indoor and outdoor event space. Highlights Prime downtown location just steps from Mallory Square and Duval StreetOn-site, 37-slip marina accommodates boats from 25 to 200 feetFree Wi-Fi access public areas, fees apply in guestroomsHotel has a pet policy Rooms The Westin Key West Resort & Marina offers 178 immaculate guestrooms and suites. Guestrooms have either king beds or pairs of queens, and the one- or two-bedroom suites have king-size beds and pullout sofas in the living areas. Suites and deluxe guestrooms have patios or balconies with ocean or garden views. In-room amenities for all accommodations include flat-screen TVs, Wi-Fi access (fees apply), coffee makers, and stocked mini bars. The Westin Key West Resort & Marina has a pet policy and can provide dog beds on request. Bathrooms come equipped with fluffy bathrobes and slippers. Features The Westin Key West Resort & Marina has earned the AAA Four-Diamond rating every year since 1999, and this waterfront Key West resort in downtown Key West boasts a full-service, 37-slip marina that can accommodate boats up to 200 feet long. Guests of the Westin Key West Resort & Marina can arrange watersports and charters, and on-site activities include an outdoor heated pool and Jacuzzi, 24-hour fitness room, and massage studio. Guests can find both fine and casual dining at the hotel-the premiere restaurant Bistro 245 serves seafood and steaks overlooking the harbor. Business travelers and event groups can find a 24-hour business center with free Wi-Fi, and more than 16,000 square feet of flexible, indoor and outdoor event space. Transportation Key West International Airport (4.2 mi./6.7 km)Miami International Airport (159 mi./254.4 km) Attractions Mallory Square (next door)Smathers Beach (3.3 mi./5.3 km)Harry S. Truman Little White House (0.2 mi./0.3 km) Business 24-hour business center16,000 square feet of flexible indoor/outdoor event spaceFree Wi-Fi in public areas
Value Save 25% on your stay
Nightly rates from $344

Hyatt Key West Resort and Spa

5 stars
4.4 / 5 89 reviews
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 near Mallory Square. Hyatt Key West Resort and Spa guests can step out the front door to find sunset sails, fishing charters and the world-famous attractions of the Key West waterfront and historic district.   HighlightsDowntown location steps away from Mallory Square and Duval StreetJala Spa offers massage, facial and full-body treatmentsWireless Internet access throughout the hotel (fees apply) RoomsAll 118 renovated guestrooms at the Hyatt Key West Resort and Spa undergo Hyatt's signature Respire hypoallergenic cleaning process to reduce airborne particles and ensure the utmost cleanliness of all fabrics and surfaces. Rooms have either single king beds or pairs of double beds fitted with luxurious linens and plush pillow-top mattresses. Guests can relax on private furnished balconies with pool and ocean views. In-room amenities include mini refrigerators, flat screen TVs, iHome stereos with iPod docking stations, in-room safes, work desks and Wi-Fi access (fees apply). DiningFor meals, Hyatt Key West Resort and Spa guests indulge in gourmet plates at the SHOR American Seafood Grill, or lighter fare and cocktails at the Blue Mojito Pool Bar and Grill. The hotel also provides  room service and catering. RecreationThe luxuriously renovated Hyatt Key West Resort and Spa offers immaculate amenities at the heart of Key West's historic district. Guests craving to be pampered book massages, facial or body treatments at Jala Spa, while adventure seekers can find a host of water sports, including scuba diving, Jet Skis and fishing charters. A fitness center allows guests not to miss a workout. For the ultimate leisure experience, guests flock to the outdoor pool and hot tub overlooking the Gulf of Mexico TransportationKey West International Airport (4 mi/6.4 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (0.2 mi/0.3 km)Sloppy Joe's Bar (0.2 mi/0.3 km)Ernest Hemingway Museum (1 mi/1.6 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessBusiness centerFlexible indoor/outdoor meeting spaces Policies and fees Valet parking fee is $15.00 per night; self parking is already included in the resort feeThere will be Resort Fee of $20 plus tax per room, per night. The fee covers the following items: High Speed wireless Internet access in the guest room, local telephone calls, 800/888 telephone surcharges, incoming faxes, complimentary self-parking, in-room bottled water, and Stay Fit 24 hour access.
Nightly rates from $259

Key West Marriott Beachside Hotel

4 stars
4.1 / 5 65 reviews
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 Key West Golf Club and a complimentary downtown shuttle. From the Key West Marriott Beachside Hotel, it's 4 miles to Mallory Square and the bars, restaurants, and shopping along Duval Street. For weddings and events, the Key West Marriott Beachside Hotel boasts the largest ballroom of any Key West hotel. Highlights Suites feature gourmet kitchensComplimentary shuttle to airport and downtown Key WestHigh-speed Internet access (free) in guestrooms and suites Rooms The Key West Marriott Beachside Hotel features 93 standard guestrooms, and 129 one-, two-, and three-bedroom suites. All accommodations have king-size beds with pillow-top mattresses, and three-bedroom suites also have pairs of twin beds in the third bedrooms. Suites boast gourmet kitchens, spa tubs, living rooms and balconies. In-room amenities for all accommodations include marble bathrooms, work desks with ergonomic chairs, coffee makers, and free high-speed Internet access. Features The sprawling seven-acre compound of the Key West Marriott Beachside Hotel boasts a wide array of amenities and activities. Guests can choose from several restaurants and dining options including contemporary fare at Tavern N' Town, room service and casual meals at the poolside Blue Bar.   Golfers can tee off at the nearby Key West Golf Club, and the hotel has a private beach, pool, hot tub, and a fitness center. The Key West Marriott Beachside Hotel also offers complimentary shuttle service to downtown Key West and the airport.   Business travelers can find a full-service business center with high-speed Internet (free) and print, copy, and fax services. And the hotel boasts 7,100 square feet of flexible event space, including the Flagler Ballroom, which can seat 450. Transportation Key West International Airport (1.1 mi./1.8 km)Miami International Airport (160 mi./256 km) Attractions Mallory Square (3.2 mi./5.1 km)Key West Golf Club (2.1 mi./3.4 km)Fort Zachary Taylor (3 mi./4.8 km)Smathers Beach (3 mi./4.8 km)Key West Aquarium (3 mi./4.8 km) Business Full-service business centerPrint, copy, fax servicesWi-Fi access (free)7,100 square feet of meeting space
Value Rate includes breakfast
Nightly rates from $362

Southernmost on the Beach

4 stars
4.5 / 5 98 reviews
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 or visit the pier for front row seats of spectacular sunrises and sunsets over the Atlantic Ocean. The hotel also boasts a junior-size Olympic pool with an oceanfront bar and massage services. HighlightsLocated waterfront along a quiet stretch of beach on the south side of Key WestAll rooms and suites offer either oceanfront access or ocean viewsFree Wi-Fi throughout the hotel RoomsThe hotel offers 123 guestrooms, 80 of them newly built, all decorated with dark mahogany furniture and blue and white accents that lend a nautical feel. Guestrooms come in ocean-view and oceanfront styles with either single kings or pairs of queen beds. Custom-designed penthouse suites add to the luxury. In-room amenities include coffee makers, mini refrigerators, iPod docks and free Wi-Fi access. DiningThe pool bar serves cocktails and a light lunch menu, while the nearby Southernmost Beach Cafe dishes up fresh seafood and waterfront views.    RecreationAs part of the Southernmost Hotel Collection, Southernmost on the Beach sits among its sister properties along the south coast of Key West. Guests can relax in hammocks or beach chairs on the private beach or take a dip in the outdoor pool. Massage services and a fitness center round out the leisure offerings. TransportationKey West International Airport (3.2 mi/5.1 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (1.2 mi/1.9 km)Key West Butterfly and Nature Conservatory (1 block)Ernest Hemingway Museum (.5 mi/.8 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessCopy and fax services (fees apply)Meeting spacesOn-site event coordinatorFree Wi-Fi  
Value Free WIFI and Free Parking
Nightly rates from $203

Casa Marina Resort - Waldorf Astoria Collection

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 largest private beach on Key West, boasting Mediterranean-style accommodations with sweeping views of the ocean, palm trees and native flowers. From here, guests can explore Duval Street or historic Old Town, enjoy endless water sports or just catch some warm sunshine on the sand. HighlightsHistoric Landmark hotel located on a private beach on the south of the islandBeachfront water sports center offers diving, fishing, dolphin encountersWi-Fi access (fees apply)Has a pet policy (fees apply) RoomsThe Casa Marina Resort offers guestrooms and one- and two-bedroom suites that open to private balconies or patios. In-room amenities include plush bathrobes and bedding, espresso machines, and mini refrigerators, LCD TVs, iHome clock radios  and Wi-Fi access (fees apply). Bathrooms come stocked with 100-percent-vegan LXR Clear beauty products. FeaturesThe recently restored, historic Casa Marina Resort boasts an on-site health club, two outdoor swimming pools, and the largest private beach on Key West. The hotel has a private pier, and Key West Watersports offers rentals and excursions from the beach. Other on-site amenities include a fitness center, beach volleyball, pool toys, hammocks and poolside concierge service. TransportationKey West International Airport (2 mi./3.2 km)Miami International Airport (158 mi./252.8 km) AttractionsMallory Square (1.8 mi./2.9 km)Harry S. Truman Little White House (1.7 mi./2.7 km)Key West Lighthouse Museum (1 mi./1.6 km)   BusinessOffice rentalsInternet kiosksCopy, print, fax and secretarial services22,600 square feet of flexible indoor/outdoor event space Policies and FeesThe hotel requires a one-night deposit fee at the time of booking.
Value Winter Offer - Save 20% on your stay
Nightly rates from $194

The Reach Resort - Waldorf Astoria Collection

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 short walk frofm the Duval Street scene and about a mile from Mallory Square.  Guests can unwind in rooms with private balconies overlooking the ocean, relax by the outdoor pool or arrange water sports on the beach. HighlightsLocated on 450 feet of Key West's only natural sand beachBeachfront water sports centerWi-Fi access (fees apply) RoomsThe resort has many flavors of rooms and suites, all of which open onto private balconies--some have ocean views, others have pool or island views. Reach Resort rooms come with single king or two double beds, and suites have king beds and sitting areas with sleeper sofas. Bathrooms are stocked with plush bathrobes and LXR Clear beauty products, while in-room amenities include espresso machines, mini refrigerators, work desks and high-tech gear like LCD TVs, iHome clock radios and Wi-Fi access for a fee. DiningStrip House restaurant serves breakfast, lunch, dinner and room service, including prime-cut steaks and an extensive wine list.    RecreationDuring 2006 and 2007, Reach Resort underwent a $37 million USD renovation. Sitting along 450 feet of the island's only natural beach, the property features an outdoor pool and a beachfront water sports operator for boat, bike, kayak and Jet Ski rentals along with scuba, snorkeling and fishing excursions. Reach Resort guests have access to the facilities at a sister property, Casa Marina Resort, including spa services. TransportationKey West International Airport (3.2 mi/5.1 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (1.4 mi/2.2 km)Key West Golf Club (5 mi/8 km)Ernest Hemingway Museum (.6 mi/1 km) BusinessWi-Fi access (fees apply)4,706 square feet of flexible meeting space Policies and FeesA $25 USD ($28.13 USD including tax) daily resort charge includes Wi-Fi, in-room espresso, local and 800 phone calls, weekday newspaper and access to Reach Resort and Casa Marina property amenities.
Value Save 15% - Any Weekend, Anywhere Sale
Nightly rates from $298

Santa Maria Suites Resort

4 stars
4.7 / 5 26 reviews
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. However, at just a mile from Mallory Square, it's conveniently close enough to the shopping and nightlife of Old Town, as well as to local watersports and charter boats.  The on-site Ambrosia restaurant serves sushi and other Japanese fare, and the Santa Maria Suites Resort provides complimentary in-room Wi-Fi access. Highlights Two-bedroom suites boast full, gourmet kitchensOutdoor pools with chilled towels and fresh smoothies prepared poolsideOn-site sushi restaurantBeach accessWi-Fi access (free) Rooms The Santa Maria Suites Resort features high-end, two-bedroom suites with luxurious amenities to pamper guests while providing all the conveniences of home. Suites feature king- or queen-size beds in bedrooms. The extravagant kitchens boast custom white cabinets topped by sea-foam granite along with a full complement of appliances-including Jenn-Air cooktops and Sub-Zero refrigerators-to make in-room entertaining easy. Bedroom amenities include flat screen televisions, custom-designed leather furniture and large closets. Master baths feature Chinese glass tiles with double Mediterranean basins and dual designer showerheads, while raised-basin sinks, marble walls, stone counters and Bath and Body Work amenities provide a spa-like feel. Accommodations also feature Wi-Fi access (free). Features The Santa Maria Suites Resort boasts a secret-garden-like courtyard surrounded by private balconies, terraces, and luxurious two bedroom accommodations. Comfortable chaises line the curves of an outdoor pool surrounded by exotic trees, fragrant native wildflowers and lavish tropical greenery. Guests can find chilled towels and fresh smoothies prepared poolside. The Santa Maria Suites Resort also features beach access, a guest parking lot, and an evening happy hour with complimentary wine. Ambrosia, the on-site restaurant, serves sushi and other Japanese delicacies. Transportation Key West International Airport (2.9 mi./4.6 km)Miami International Airport (161 mi./257.6 km) Attractions Mallory Square (1.4 mi./2.2 km)Harry S. Truman Little White House (1.3 mi./2.1 km)Fort Zachary Taylor (1.3 mi./2.1 km)Key West Lighthouse Museum (0.6 mi./1 km) Business Wi-Fi access (free)
Nightly rates from $239

Courtyard by Marriott Key West Waterfront

3 stars
4.2 / 5 26 reviews
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 large outdoor junior olympic size heated swimming pool and nearby jacuzzi, a Tiki Bar located adjacent to the pool, a private sunbathing beach, a 300 foot observation boardwalk, a free computer workstation in the lobby, complimentary in-room refrigerators and laptop size safes, and a concierge agent to help you plan your Key West vacation. Complimentary shuttle service is available to and from the downtown Key West area from 8am to 11pm.
Value Rate includes breakfast
Nightly rates from $233

Southernmost Hotel

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 the excitement when the mood strikes. For reliable day trips, guests simply stroll to restaurants, eclectic shops and art galleries nearby, along with that one constant-the Atlantic Ocean, which is across the street. Southernmost Hotel also offers free parking and Wi-Fi. HighlightsClose to the Southernmost Point of the United StatesTwo pools and a pool barSouthernmost Hotel guests also have access to amenities at nearby sister hotels Free Wi-Fi RoomsSouthernmost Hotel rooms and suites sport single kings or pairs of queen beds. Depending on the room booked, some spaces deliver pool, fountain or city views via private balconies or patios. All accommodations come equipped with free Wi-Fi, mini refrigerators, microwaves, coffee makers, hair dryers, irons and ironing boards, cable TVs and-in room safes. Some suites also have kitchenettes and living room areas. DiningFor all meals, guests can dine on fresh seafood outside on the beach at the nearby Southernmost Beach Cafe and the pool bar at the Southernmost Hotel offers cocktails and light lunch fare poolside. RecreationSouthernmost Hotel offers a nice set of free amenities that include parking, Wi-Fi throughout the property and two swimming pools.  Guests can also take advantage of the fitness center, bike rentals and massage services on site, or visit the sister property, Southernmost on the Beach, where they also have access to the beach, beach chairs, pier and oceanfront pool. TransportationKey West International Airport (2.9 mi/4.6 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (1.3 mi/2.1 km)Key West Butterfly and Nature Conservatory (1 block)Ernest Hemingway Museum (.5 mi/.8 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessFlexible indoor and outdoor meeting spaces, including  a conference room for 50 guests, plus beachfront and poolside gathering areasCatering servicesPresentation equipmentCopy and fax services (fees apply)Free Wi-Fi
Value Free: WIFI, Parking, Resort Activities!
Nightly rates from $304

Pier House Resort and Caribbean Spa

5 stars
4.4 / 5 98 reviews
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 features a private beach, boat dock and an outdoor pool amid tropical gardens. Rooms and suites ooze elegant island style with modern amenities. The full-service Caribbean Spa offers massage and beauty treatments. Highlights Located on Duval Street, at the heart of Old Town Key West and steps from Mallory SquarePrivate beach with separate, secluded topless sunbathing areaFree downtown parkingFree Wi-Fi   Rooms Guests of the Pier House Resort and Caribbean Spa choose from standard hotel rooms, lanai rooms with private patios or balconies, spa adjacent and harbor-view rooms and spacious one- and two-bedroom suites, each with a unique design theme. Accommodations sport custom furniture, single kings or pairs of queen beds and luxurious extras like rain showers or soaking tubs. In-room amenities include coffee makers, refrigerators, flat-screen TVs, in-room movies and free Wi-Fi. Dining Guests can take meals HarbourView Cafe, which serves breakfast, lunch and dinner and overlooks the ocean. When cocktail hour hits, they can sip boat drinks at any of three bars on the property, including the Chart Room Bar, a local favorite. Recreation Sprawling across a six-acre compound in the heart of Key West's famous tourist district, the Pier House Resort and Caribbean Spa offers quiet seclusion and unbeatable access to island attractions. The waterfront location features a private beach, private boat dock and an outdoor pool nestled within lush gardens. Caribbean Spa pampers with massages, facials, body treatments, nail and hair services seven days a week. Transportation Key West International Airport (4.1 mi/6.6 km)Miami International Airport (159 mi/254.4 km) Attractions Mallory Square (1 block)Fort Zachary Taylor (1.3 mi/2.1 km)Harry S. Truman Little White House (0.3 mi/0.5 km) Business 2,600-square-foot conference centerBeach and garden outdoor event spacesFull-service catering Policies and feesGuests must be 21 years old to check in. All rooms are nonsmoking.
Back to menu Return to top

Best in Stay

LGBT Best in Stay Key West hotels

Nightly rates from $233

Southernmost Hotel

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 the excitement when the mood strikes. For reliable day trips, guests simply stroll to restaurants, eclectic shops and art galleries nearby, along with that one constant-the Atlantic Ocean, which is across the street. Southernmost Hotel also offers free parking and Wi-Fi. HighlightsClose to the Southernmost Point of the United StatesTwo pools and a pool barSouthernmost Hotel guests also have access to amenities at nearby sister hotels Free Wi-Fi RoomsSouthernmost Hotel rooms and suites sport single kings or pairs of queen beds. Depending on the room booked, some spaces deliver pool, fountain or city views via private balconies or patios. All accommodations come equipped with free Wi-Fi, mini refrigerators, microwaves, coffee makers, hair dryers, irons and ironing boards, cable TVs and-in room safes. Some suites also have kitchenettes and living room areas. DiningFor all meals, guests can dine on fresh seafood outside on the beach at the nearby Southernmost Beach Cafe and the pool bar at the Southernmost Hotel offers cocktails and light lunch fare poolside. RecreationSouthernmost Hotel offers a nice set of free amenities that include parking, Wi-Fi throughout the property and two swimming pools.  Guests can also take advantage of the fitness center, bike rentals and massage services on site, or visit the sister property, Southernmost on the Beach, where they also have access to the beach, beach chairs, pier and oceanfront pool. TransportationKey West International Airport (2.9 mi/4.6 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (1.3 mi/2.1 km)Key West Butterfly and Nature Conservatory (1 block)Ernest Hemingway Museum (.5 mi/.8 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessFlexible indoor and outdoor meeting spaces, including  a conference room for 50 guests, plus beachfront and poolside gathering areasCatering servicesPresentation equipmentCopy and fax services (fees apply)Free Wi-Fi
Value Free: WIFI, Parking, Resort Activities!
Nightly rates from $203

Casa Marina Resort - Waldorf Astoria Collection

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 largest private beach on Key West, boasting Mediterranean-style accommodations with sweeping views of the ocean, palm trees and native flowers. From here, guests can explore Duval Street or historic Old Town, enjoy endless water sports or just catch some warm sunshine on the sand. HighlightsHistoric Landmark hotel located on a private beach on the south of the islandBeachfront water sports center offers diving, fishing, dolphin encountersWi-Fi access (fees apply)Has a pet policy (fees apply) RoomsThe Casa Marina Resort offers guestrooms and one- and two-bedroom suites that open to private balconies or patios. In-room amenities include plush bathrobes and bedding, espresso machines, and mini refrigerators, LCD TVs, iHome clock radios  and Wi-Fi access (fees apply). Bathrooms come stocked with 100-percent-vegan LXR Clear beauty products. FeaturesThe recently restored, historic Casa Marina Resort boasts an on-site health club, two outdoor swimming pools, and the largest private beach on Key West. The hotel has a private pier, and Key West Watersports offers rentals and excursions from the beach. Other on-site amenities include a fitness center, beach volleyball, pool toys, hammocks and poolside concierge service. TransportationKey West International Airport (2 mi./3.2 km)Miami International Airport (158 mi./252.8 km) AttractionsMallory Square (1.8 mi./2.9 km)Harry S. Truman Little White House (1.7 mi./2.7 km)Key West Lighthouse Museum (1 mi./1.6 km)   BusinessOffice rentalsInternet kiosksCopy, print, fax and secretarial services22,600 square feet of flexible indoor/outdoor event space Policies and FeesThe hotel requires a one-night deposit fee at the time of booking.
Value Winter Offer - Save 20% on your stay
Nightly rates from $298

Santa Maria Suites Resort

4 stars
4.7 / 5 26 reviews
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. However, at just a mile from Mallory Square, it's conveniently close enough to the shopping and nightlife of Old Town, as well as to local watersports and charter boats.  The on-site Ambrosia restaurant serves sushi and other Japanese fare, and the Santa Maria Suites Resort provides complimentary in-room Wi-Fi access. Highlights Two-bedroom suites boast full, gourmet kitchensOutdoor pools with chilled towels and fresh smoothies prepared poolsideOn-site sushi restaurantBeach accessWi-Fi access (free) Rooms The Santa Maria Suites Resort features high-end, two-bedroom suites with luxurious amenities to pamper guests while providing all the conveniences of home. Suites feature king- or queen-size beds in bedrooms. The extravagant kitchens boast custom white cabinets topped by sea-foam granite along with a full complement of appliances-including Jenn-Air cooktops and Sub-Zero refrigerators-to make in-room entertaining easy. Bedroom amenities include flat screen televisions, custom-designed leather furniture and large closets. Master baths feature Chinese glass tiles with double Mediterranean basins and dual designer showerheads, while raised-basin sinks, marble walls, stone counters and Bath and Body Work amenities provide a spa-like feel. Accommodations also feature Wi-Fi access (free). Features The Santa Maria Suites Resort boasts a secret-garden-like courtyard surrounded by private balconies, terraces, and luxurious two bedroom accommodations. Comfortable chaises line the curves of an outdoor pool surrounded by exotic trees, fragrant native wildflowers and lavish tropical greenery. Guests can find chilled towels and fresh smoothies prepared poolside. The Santa Maria Suites Resort also features beach access, a guest parking lot, and an evening happy hour with complimentary wine. Ambrosia, the on-site restaurant, serves sushi and other Japanese delicacies. Transportation Key West International Airport (2.9 mi./4.6 km)Miami International Airport (161 mi./257.6 km) Attractions Mallory Square (1.4 mi./2.2 km)Harry S. Truman Little White House (1.3 mi./2.1 km)Fort Zachary Taylor (1.3 mi./2.1 km)Key West Lighthouse Museum (0.6 mi./1 km) Business Wi-Fi access (free)
Nightly rates from $304

Pier House Resort and Caribbean Spa

5 stars
4.4 / 5 98 reviews
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 features a private beach, boat dock and an outdoor pool amid tropical gardens. Rooms and suites ooze elegant island style with modern amenities. The full-service Caribbean Spa offers massage and beauty treatments. Highlights Located on Duval Street, at the heart of Old Town Key West and steps from Mallory SquarePrivate beach with separate, secluded topless sunbathing areaFree downtown parkingFree Wi-Fi   Rooms Guests of the Pier House Resort and Caribbean Spa choose from standard hotel rooms, lanai rooms with private patios or balconies, spa adjacent and harbor-view rooms and spacious one- and two-bedroom suites, each with a unique design theme. Accommodations sport custom furniture, single kings or pairs of queen beds and luxurious extras like rain showers or soaking tubs. In-room amenities include coffee makers, refrigerators, flat-screen TVs, in-room movies and free Wi-Fi. Dining Guests can take meals HarbourView Cafe, which serves breakfast, lunch and dinner and overlooks the ocean. When cocktail hour hits, they can sip boat drinks at any of three bars on the property, including the Chart Room Bar, a local favorite. Recreation Sprawling across a six-acre compound in the heart of Key West's famous tourist district, the Pier House Resort and Caribbean Spa offers quiet seclusion and unbeatable access to island attractions. The waterfront location features a private beach, private boat dock and an outdoor pool nestled within lush gardens. Caribbean Spa pampers with massages, facials, body treatments, nail and hair services seven days a week. Transportation Key West International Airport (4.1 mi/6.6 km)Miami International Airport (159 mi/254.4 km) Attractions Mallory Square (1 block)Fort Zachary Taylor (1.3 mi/2.1 km)Harry S. Truman Little White House (0.3 mi/0.5 km) Business 2,600-square-foot conference centerBeach and garden outdoor event spacesFull-service catering Policies and feesGuests must be 21 years old to check in. All rooms are nonsmoking.
Nightly rates from $344

Hyatt Key West Resort and Spa

5 stars
4.4 / 5 89 reviews
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 near Mallory Square. Hyatt Key West Resort and Spa guests can step out the front door to find sunset sails, fishing charters and the world-famous attractions of the Key West waterfront and historic district.   HighlightsDowntown location steps away from Mallory Square and Duval StreetJala Spa offers massage, facial and full-body treatmentsWireless Internet access throughout the hotel (fees apply) RoomsAll 118 renovated guestrooms at the Hyatt Key West Resort and Spa undergo Hyatt's signature Respire hypoallergenic cleaning process to reduce airborne particles and ensure the utmost cleanliness of all fabrics and surfaces. Rooms have either single king beds or pairs of double beds fitted with luxurious linens and plush pillow-top mattresses. Guests can relax on private furnished balconies with pool and ocean views. In-room amenities include mini refrigerators, flat screen TVs, iHome stereos with iPod docking stations, in-room safes, work desks and Wi-Fi access (fees apply). DiningFor meals, Hyatt Key West Resort and Spa guests indulge in gourmet plates at the SHOR American Seafood Grill, or lighter fare and cocktails at the Blue Mojito Pool Bar and Grill. The hotel also provides  room service and catering. RecreationThe luxuriously renovated Hyatt Key West Resort and Spa offers immaculate amenities at the heart of Key West's historic district. Guests craving to be pampered book massages, facial or body treatments at Jala Spa, while adventure seekers can find a host of water sports, including scuba diving, Jet Skis and fishing charters. A fitness center allows guests not to miss a workout. For the ultimate leisure experience, guests flock to the outdoor pool and hot tub overlooking the Gulf of Mexico TransportationKey West International Airport (4 mi/6.4 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (0.2 mi/0.3 km)Sloppy Joe's Bar (0.2 mi/0.3 km)Ernest Hemingway Museum (1 mi/1.6 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessBusiness centerFlexible indoor/outdoor meeting spaces Policies and fees Valet parking fee is $15.00 per night; self parking is already included in the resort feeThere will be Resort Fee of $20 plus tax per room, per night. The fee covers the following items: High Speed wireless Internet access in the guest room, local telephone calls, 800/888 telephone surcharges, incoming faxes, complimentary self-parking, in-room bottled water, and Stay Fit 24 hour access.
Nightly rates from $362

Southernmost on the Beach

4 stars
4.5 / 5 98 reviews
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 or visit the pier for front row seats of spectacular sunrises and sunsets over the Atlantic Ocean. The hotel also boasts a junior-size Olympic pool with an oceanfront bar and massage services. HighlightsLocated waterfront along a quiet stretch of beach on the south side of Key WestAll rooms and suites offer either oceanfront access or ocean viewsFree Wi-Fi throughout the hotel RoomsThe hotel offers 123 guestrooms, 80 of them newly built, all decorated with dark mahogany furniture and blue and white accents that lend a nautical feel. Guestrooms come in ocean-view and oceanfront styles with either single kings or pairs of queen beds. Custom-designed penthouse suites add to the luxury. In-room amenities include coffee makers, mini refrigerators, iPod docks and free Wi-Fi access. DiningThe pool bar serves cocktails and a light lunch menu, while the nearby Southernmost Beach Cafe dishes up fresh seafood and waterfront views.    RecreationAs part of the Southernmost Hotel Collection, Southernmost on the Beach sits among its sister properties along the south coast of Key West. Guests can relax in hammocks or beach chairs on the private beach or take a dip in the outdoor pool. Massage services and a fitness center round out the leisure offerings. TransportationKey West International Airport (3.2 mi/5.1 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (1.2 mi/1.9 km)Key West Butterfly and Nature Conservatory (1 block)Ernest Hemingway Museum (.5 mi/.8 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessCopy and fax services (fees apply)Meeting spacesOn-site event coordinatorFree Wi-Fi  
Value Free WIFI and Free Parking
Nightly rates from $229

Crowne Plaza KEY WEST-LA CONCHA

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 access, and the rooftop observation deck is the ideal place to sip a drink and watch the sunset. And from the Crowne Plaza Hotel Key West, guests can easily stroll to nearby attractions like the Hemingway House and Mallory Square, and iconic bars like Sloppy Joe's line the surrounding streets. HighlightsCentral location at the heart of Old Town Key WestTallest building on the island offers incredible views of the cityFree Wi-Fi access throughout RoomsAt Crowne Plaza Hotel Key West - La Concha, plush guestrooms and suites offer great views of the Old Town and feature plush, elegant island furnishings and modern amenities. Rooms come with either two queen beds or single kings, and suites have king beds and queen-size sleeper sofas. All accommodations have 42-inch flat screen TVs, coffee makers, hair dryers and free Wi-Fi. Some rooms also have French doors that open to spacious balconies. FeaturesThe central location of Crowne Plaza Hotel Key West - La Concha makes it an ideal base from which to explore the city, while the sundeck and the rooftop bar offer excellent vantage points of Old Town and sunsets over the Atlantic. The hotel features a collection of bars and restaurants, including fresh seafood overlooking Duval Street at Jack's Seafood Shack and a Starbucks. On-site amenities at Crowne Plaza Hotel Key West - La Concha include an outdoor pool and 24-hour fitness center. TransportationKey West International Airport (3.7 mi/5.9 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (.5 mi/.8 km)Key West Aquarium (.5 mi/.8 km)Ernest Hemingway Home and Museum (.5 mi/.8 km) BusinessFlexible meeting spacesBusiness center with computers and print, copy and fax services Free Wi-Fi
Back to menu Return to top

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
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.

Please type the date in the following format: M/d/yy . For example: January 3, 2013 would be entered as 1/3/13 .

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

Please type the date in the following format: M/d/yy . For example: January 3, 2013 would be entered as 1/3/13 .
Room 1
Age categories
Ages of children at time of trip (for pricing, discounts)

Additional search options

0