Destinations / North America

Key West’s Most Fabulous Gay Resorts & Hotels for 2019

Key West is an LGBTQ holiday paradise where gay travellers can feel at home while lounging on white-sand beaches, partying in all-night clubs or browsing the city’s eclectic boutiques. Higg’s Beach is the unofficial gay beach in Key West, blessed with fiery sunsets and colourful reefs, while Duval Street dishes up beautiful Spanish architecture and Cuban culture.

Are you looking for a gay-oriented resort or hotel in Key West? With more than 400 million annual visitors to HotelsCombined, we’ve tracked down the best gay resorts and hotels in Key West for 2019. These fabulous accommodations not only cater to gay guests, but also provide delectable extras, such as on-site dining and leisure facilities.

Alexander’s Key West

Alexander's Key WestThe award-winning Alexander’s Key West is a popular LGBTQ guesthouse housed within a restored Key West conch house with original elements and modern luxuries. The three-storey house offers a laid-back lifestyle with its inviting communal areas, including the sun-dappled swimming pool and Jacuzzi, three levels of sun decks with loungers and breakfast restaurant.

Accommodation ranges from contemporary guest rooms with king-size beds, flat-screen TVs and wet bars to suites with French doors that open out to private gardened patios. You can upgrade your room to include a private balcony overlooking the pool or garden or splurge on The Apartment, which boasts a full kitchen, large living room, dining room, private sun deck and covered balcony. 

Why You Should Stay Here

  • Fruity cocktails served poolside at Pink Monkey Bar.
  • Delicious daily breakfast of fresh juice, homemade muffins, tropical fruits and island-style iced tea.
  • About a 10-minute walk from the cafes and restaurants on the Key West Bight.

Star Rating: No Rating
Price: USD 240 – USD 521
Guest Rating: No Rating
Address: 1118 Fleming St, Key West, Florida, United States

Cypress House

Cypress HouseLocated in Key West’s historic city centre, Cypress House has won over HotelsCombined visitors with its excellent location and delicious poolside breakfast of local bagels, pastries and tropical juice. Along with its heated lap pool nestled in a lush garden, this boutique hotel offers a knowledgeable concierge, eco-friendly bath products and complimentary Wi-Fi.

Cypress House celebrates Key West’s rich history with touches of 1800s colonial wood-frame architecture. All of the rooms feature mini fridges, air conditioning, complimentary breakfast and flat-screen TVs. Upgrade to the Deluxe King Guest Room with traditional French doors that open onto a private furnished porch. 

Why You Should Stay Here 

Star Rating: 3*
Price: USD 171 – USD 399
Guest Rating: 9.1
Address: 601 Caroline Street, Key West, Florida, United States

Hyatt Key West Resort and Spa

Hyatt Key West Resort and SpaEnjoy waterfront accommodation with a boutique twist at Hyatt Key West Resort and Spa. Choose from 120 pet-friendly rooms with private balconies overlooking the Gulf of Mexico. These rooms offer two queen-size beds or one king-size bed, along with island-style decor, work desks and signature Hyatt Grand Beds.

On-site dining is highlighted by the fresh seafood and award-winning Key lime pie sold at SHOR American Seafood Grill. You can also indulge in fish tacos and the signature Blue Mojito at Blue Mojito Pool Bar and Grill. Laze around by the sun-drenched pool, work out in the fitness centre or enjoy a soothing massage at Jala Spa. 

Why You Should Stay Here 

  • The private balcony, sitting area and ocean vistas in the 1 King Premium.
  • A dog-friendly hotel on Key West Bight, minutes from downtown restaurants and bars.
  • The 80-minute Jala Signature Massage at Jala Spa. 

Star Rating: 4*
Price: USD 372 – USD 671
Guest Rating: 8.9
Address: 601 Front Street, Key West, Florida, United States

Island House Key West Resort

Island House Key West ResortArguably one of the world’s best gay resorts, Island House Key West Resort is a community of like-minded gay travellers seeking a social and relaxing Florida playground. The all-male resort has a clothing-optional policy that extends to its two large Jacuzzis, palm-encircled swimming pool, outdoor shower and erotic video lounge. All guests receive free drinks during the daily happy hour at the poolside cafe and bar, along with access to the 24-hour fitness centre.

The comfortable and modern rooms feature feather-topped beds, flat-screen TVs and fridges. Some rooms overlook historic Fleming Street, while others have a view of the pool area. Save money on a room with a shared bathroom or splurge on a two-bedroom apartment with a full kitchen, wet bar, private porch and living room.

Why You Should Stay Here 

  • Numerous events and parties, including Bone Island Bare-It-All weekends, Tropical Heat and Gay Pride celebrations.
  • The private entry, porch, full kitchen, bar and three TVs in the AP2X room.
  • Complimentary custom sarongs, happy hour and parking. 

Star Rating: 3*
Price: USD 308 – USD 440
Guest Rating: 9.4
Address: 411 William Street, Key West, Florida, United States

Hotel at La Te Da Key West

Hotel at La Te Da Key West

La Te Da’s boutique hotel is a hotspot for gay travellers, thanks to Floridian-style guest rooms and a prime location on Duval Street. There are over 30 rooms to choose from, including a cottage-style room with direct pool access, a room with a private porch and pool views and a Deluxe Room with vintage surf photography.

Along with a glamorous on-site pool, this hotel has its own restaurant, which serves fresh seafood and other local specialties. You can enjoy wine, beer and cocktails and Duval Street views at the Terrace Bar, then visit the Piano Bar for an evening of live entertainment. 

Why You Should Stay Here 

Star Rating: 3*
Price: USD 213 – USD 447
Guest Rating: 9.3
Address: 1125 Duval Street, Key West, Florida, United States

Southernmost Beach Resort

Southernmost Beach ResortThe Southernmost Beach Resort takes its name from being near the Southernmost Point of the Continental U.S. Tucked into Key West’s Historic Old Town, this charming resort features massage cabanas overlooking the Gulf of Mexico, a full gym and yoga classes. It also has three pools with sun loungers and two poolside bars. Don’t forget to indulge in classic Americana and Asian-fusion cuisine at Southernmost Beach Café.

Superior Rooms feature queen-size beds, while Deluxe Rooms offer king-size beds. Upgrade to an oceanfront or ocean-view room to capture water vistas or splurge on the Simonton Suite, a private two-storey residence with high-end appliances, soaking tubs, three bedrooms and direct beach access. 

Why You Should Stay Here 

  • Mini fridges, air conditioning and large HDTVs in all rooms and suites.
  • Access to the southernmost beaches in the continental U.S.
  • A range of massages, facials, waxing and pedicures at Petite Spa. 

Star Rating: 4*
Price: USD 276 – USD 965
Guest Rating: 8.9
Address: 508 South Street, Key West, Florida, United States

Pegasus International Hotel

Pegasus International HotelLocated on Duval Street, Pegasus International Hotel surrounds you with high-energy bars and clubs and fine-dining restaurants. The well-appointed rooms and suites boast Art Deco interior design, hi-tech entertainment and complimentary breakfast. Need extra space? Book one of the suites for two separate bedrooms and a large living room with a pull-out sofa.

Cool off at the outdoor swimming pool, which has a Jacuzzi and a poolside bar serving snacks and refreshments. Both are located on a rooftop deck, which is perfect for parties. Right outside you’ll find inviting local boutiques, such as the Paradise Vision swimwear store and Forever Young t-shirt shop. 

Why You Should Stay Here 

  • A two-minute walk from Margaritaville Restaurant Key West.
  • On-site pool and rooftop deck serving Key West seafood.
  • Hypoallergenic pillows, free bottles of water and ELEMIS beauty products in all rooms and suites.

Star Rating: 3*
Price: USD 242 – USD 462
Guest Rating: 7.9
Address: 501 Southard Street, Key West, Florida, United States

Ocean Key Resort & Spa a Noble House Resort

Ocean Key Resort Spa a Noble House Resort 2The extravagant Ocean Key Resort & Spa a Noble House Resort is nestled at the northern tip of Duval Street overlooking the picturesque Gulf of Mexico. This 4-star resort has cemented its highly-regarded reputation with its Hot Tin Roof Restaurant serving conch-fusion cuisine, along with the on-site SpaTerre’s Thai body rituals. It tops all this off with a fitness centre, the LIQUID pool, bar and lounge and business services.

Choose from bright and modern rooms, suites and penthouses, including oceanfront rooms with four-poster beds, spa baths and balconies. The Island View Junior Suite features a furnished balcony, whirlpool tub and stocked mini bar, while the 2 Bedroom Oceanfront Penthouse has a deep-soaking bath, Dorado stone floors and fifth-floor ocean vistas. 

Why You Should Stay Here 

  • A range of accommodation styles for small budgets and those seeking luxury.
  • Fruity cocktails and gourmet sandwiches at LIQUID Bar and Lounge.
  • Located next to the Mallory Square shops, restaurants and sunset celebrations. 

Star Rating: 4*
Price: USD 319 – USD 1,082
Guest Rating: 9.2
Address: Zero Duval Street, Key West, Florida, United States

The Marker Waterfront Resort

The Marker Waterfront ResortThe Marker Waterfront Resort occupies a prime spot on Key West’s historic harbour and is one of the newest hotels in the city. The resort’s signature restaurant, Cero Bodega, serves cocktails and Cal-Mex cuisine, while the poolside bar complements the alluring pool with its Spanish wine and margaritas. There are two more pools, along with a fitness centre and bicycle rentals.

The Marker Classic Rooms pair traditional furnishings with modern comforts, including plush beds and private balconies. Stay in a Pool Garden Room for views over the resort’s main pool or the Key West Harbor Room for harbour vistas. Splurge on The Captain’s Quarters for a king-size bed, bathrobes, furnished balcony and curated mini bar.

Why You Should Stay Here 

  • Three on-site pools and a state-of-the-art fitness centre.
  • A two-minute walk from Turtle Cannery Museum.
  • Down the street from the iconic Schooner Wharf Bar, known for its live music and dockside views. 

Star Rating: 4*
Price: USD 276 – USD 1,658
Guest Rating: 9.1
Address: 200 William Street, Key West, Florida, United States

New Orleans House – Gay Male-Only Guesthouse

New Orleans House - Gay Male-Only GuesthouseThe only all-male guesthouse on Duval Street, New Orleans House caters to gay men looking to meet fellow travellers and embrace Key West’s vibrant culture, entertainment and late-night lifestyle. The guesthouse is home to the popular Bourbon Street Pub, which features live shows and nightly VJs. You also have access to a clothing-optional garden bar with a pool and 15-person Jacuzzi.

There are various rooms available, including a one-bedroom apartment with a fully-equipped kitchen and the budget-friendly Room 22A with a balcony overlooking Duval Street. All the rooms have cable TV, air conditioning, complimentary breakfast and happy hours and fridges. 

Why You Should Stay Here 

  • A clothing-optional sundeck with a pool and Jacuzzi.
  • Free drag shows every night.
  • Low-price rooms with shared bathrooms for budget-savvy travellers. 

Star Rating: 2.5*
Price: USD 193 – USD 318
Guest Rating: 8.7
Address: 724 Duval Street, Key West, Florida, United States

The Gates Hotel Key West

The Gates Hotel Key WestLooking for a secluded Key West paradise away from the crowds? The Gates Hotel Key West is a pet-friendly sanctuary with visually-stunning grassy lawns and a sun-drenched pool. The poolside bar, Rum Row, has local rums, a cigar lounge and a food truck while also hosting live music. 

Rest peacefully in the comfortable and stylish rooms, which feature sunlit windows, natural finishes and plush bedding. The Lifestyle King is one of the closest rooms to the pool, while The Scene features a private poolside terrace. Save money on the Standard King, which overlooks gardens and has lounge seating. 

Why You Should Stay Here 

  • About a 15-minute walk from Key West Tropical Forest & Botanical Garden.
  • Prime location away from tourist crowds on Duval Street.
  • A hip on-site bar and food truck with live music. 

Star Rating: No Rating
Price: USD 212 – USD 352
Guest Rating: 8.6
Address: 3824 North Roosevelt Blvd, Key West, Florida, United States

Pier House Resort & Spa

Pier House Resort & SpaNestled on the edge of Key West’s historic harbour, Pier House Resort & Spa combines the best of Key West’s waterside attractions with Duval Street’s restaurants, bars, shops and clubs. The pet-friendly resort has an opulent spa offering restorative therapies, while the on-site pool has a poolside bar and a hot tub.

Delve into locally-sourced organic cuisine at One Duval or enjoy cocktails and casual dining at Beach Bar and Chart Room Bar. The rooms and suites include Traditional Rooms with pillow-top mattresses and rain showers. The Lanais have balconies or patios, while the suites offer luxurious extras like Gulf of Mexico views and free-standing baths. 

Why You Should Stay Here 

  • The 50-minute Duval Detox Body Wrap at the on-site spa.
  • Located next to the waterfront Lagerheads Beach Bar & Watersports.
  • The hot tub, multi-seat bar, king-size four-poster beds and ocean-facing balconies in the expansive Presidential Suite. 

Star Rating: 4*
Price: USD 409 – USD 558
Guest Rating: 8.9
Address: One Duval Street, Key West, Florida, United States

The Perry Hotel Key West

The Perry Hotel Key WestThe Perry Hotel Key West offers a completely different environment to any hotel or resort on this list. Its Stock Island locale is just the beginning of its authentic Key West atmosphere, heightened by the charming marina village outside. The boutique hotel captures yester-year charm while providing modern luxuries in its cosy rooms, which have water views, private balconies, local artwork and work desks.

Along with a welcome glass of champagne and complimentary shuttles to Old Town, this hotel offers a waterfront pool, outdoor fire pits and two dog parks. Browse the souvenirs at Green Pineapple Boutique, organise water sports on site or dine on boat-to-table seafood at Salty Oyster.  

Why You Should Stay Here 

  • The marina views, wraparound porch, wet bar, living room and separate bath in the Grand Suite.
  • American comfort food and happy-hour specials at Matt’s Stock Island Kitchen & Bar.
  • Direct access to Stock Island Marina Village. 

Star Rating: 4*
Price: USD 246 – USD 937
Guest Rating: 9.2
Address: 7001 Shrimp Rd, Key West, Florida, United States

Nyah – Adult Exclusive

Nyah - Adult ExclusiveThe adults-only Nyah is an extravagant hotel ideal for those seeking pampering facilities, including three pools and two Jacuzzis. Rent bicycles on site to explore the Old Town or simply chill in a sun lounger with a cocktail from the bar, which has a daily happy hour.

The hotel offers a unique “Build Your Own Room” concept, letting you tailor your room to accommodate up to six guests without paying extra. These customisable rooms have memory foam mattresses and beds that can be converted into king-size beds or single bunks. They also boast TVs, fridges and extra seating. 

Why You Should Stay Here 

  • A wealth of on-site leisure facilities, including three pools and a bar.
  • Customisable rooms able of accommodation one to six guests.
  • About a 10-minute walk from Duval Street.

Star Rating: 2*
Price: USD 209 – USD 488
Guest Rating: 8.8
Address: 420 Margaret Street, Key West, Florida, United States

Hotel Location

A Holiday with all the Trimmings in Key West

Make the most of your Key West holiday by staying at one of these extravagant resorts or hotels perfect for gay travellers. These coastal retreats range from male-only and adults-only resorts to boutique Duval Street hotels and waterfront havens. On-site perks at these glamorous holiday abodes typically include on-site dining, sun-drenched pools, day spas and Key West-inspired rooms.

Where will you stay in Key West on your vacation? Let us know in the comments below.

Author: Ben Stower

I'm enamoured with travel, whether it's finding the quiet, local sanctuaries in touristic cities, venturing into rock vaults in a distant jungle or spending hours on a Spanish beach. I can't see an end to my travelling. Just another chapter and another story to tell.

Ben Stower
I'm enamoured with travel, whether it's finding the quiet, local sanctuaries in touristic cities, venturing into rock vaults in a distant jungle or spending hours on a Spanish beach. I can't see an end to my travelling. Just another chapter and another story to tell.
Posted on Categories Destinations, North AmericaTags , ,

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