Villa C at Island Mates Manor

Welcome to Island Mates Manor, the newest modern addition to luxury gay accomodations in Old Town Key West! Located at the end of "Millionaire's Row" on Fleming Street, this newly reimagined 3-home property is your own private escape in the middle of all the action of Gay Key West. This property was meticulously designed by gay men, for gay men, and is conveniently located directly next door to "the best gay resort in the world," Island House.

Your hosts, Jeff & James, live in the historic home at the front of the property facing Fleming St. The two Villas in the rear of the property were built from the ground up in 2025. Each of the two luxury Villas feature a split-level layout (meaning three floors), and have 2 bedrooms and 2.5 bathrooms each, offering all King beds, and all bedrooms are en suites with private balconies and dedicated work/study spaces. The Villas feature ultra-modern chef-style kitchen/living areas with island dining, custom designed cabinetry, and high-end appliances. Both units have dedicated covered parking from Stickney Lane, as well as central A/C & heat, high-speed dedicated fiber internet service, and private laundry inside each unit. Guests enjoy private entrances for each Villa, with a walking path open to Fleming St. The Villas and the property owners exclusively share a large swimming pool with water ledge loungers, hot tub, pool deck with chaise, propane grill, and swim up bar with sunken lounge area under a mechanical pergola. Residents may enjoy private access to the 24-hour Island House Cafe & Bar located directly next door, and post charges directly to their house account, similar to a country club membership. You are welcome to invite friends to the property as your guests, however, Island Mates Manor will NEVER be accessible to the general population of the hotel next door. We are a pet friendly property (we're dog lovers!) with lush landscaping and ultimate privacy in mind. The pool area is a clothing-optional atmosphere free of judgement. We proudly cater to a gay male clientele, however, as a place of public accomodation we do not discriminate on the basis of sex. When mixed company can be expected, a friendly sign will be visible in the pool area to communicate that fact. When the sign is not posted, you can enjoy a clothing optional experience knowing you are in the company of fellow men. Since we are located next door to a famous gay men's resort, as well as across the street from another famous LGBTQ+ guesthouse, you can expect an experience reflective of the vibrant gay community that Key West has been famous for since the 1970's. The "gayborhood" feel is alive and well here, and we are unapologetic when it comes to providing the most unique, most luxurious, and most FUN gay accomodations that are intended as homes away from home.

Rates & Availability

Cancellation Policy: One hundred percent (100.00%) of the total booking charges (less $1,000.00 cancellation fee) will be refunded if the cancellation is made more than 90 days prior to the arrival date of the reservation. Ninety percent (90.00%) of the total booking charges (less $1,000.00 cancellation fee) will be refunded if the cancellation is made more than 60 days prior to the arrival date of the reservation. For cancellations made within 60 days prior to the arrival date, no refund will be issued. Grace period with free cancellation for 24 hours after booking if arrival is at least 72 hours away at time of booking.

Location

Key West, Florida

Amenities

Guest Reviews