In a destination famed for its uninhibited spirit and rich LGBTQ+ heritage, a new standard for modern, private luxury has arrived. Tucked away at the end of Fleming Street’s iconic “Millionaire’s Row”, Island Mates Manor is redefining what it means to experience Gay Key West in style — with all the indulgence of a resort, and the seclusion of your own private villa.

Meticulously designed by gay men, for gay men, this newly reimagined three-home estate seamlessly blends sleek, modern design with the rich history and vibrant energy that define Old Town Key West.

A Hidden Oasis, Steps from the Action

Located directly next door to Island House, widely regarded as “the best gay resort in the world,” Island Mates Manor offers guests a privileged position in the heart of Key West’s celebrated gayborhood. But unlike the bustling resort atmosphere, this property is intentionally crafted as a private, serene escape for those who appreciate luxury, discretion, and thoughtful design. At the front of the estate, your hosts, Jeff & James, reside in a beautifully preserved historic home, offering a personal touch that reflects true Southern hospitality. Nestled quietly at the rear are two ultra-modern, split-level Villas, constructed from the ground up in 2025, offering the ultimate in contemporary island living.

Design-Driven Living with Resort-Style Perks

Each villa spans three levels, with two bedrooms, 2.5 bathrooms, and airy living spaces thoughtfully curated with high-end finishes and designer details. All bedrooms are en suite, complete with king-size beds, private balconies, and dedicated work or study spaces for those blending business with pleasure.
The chef’s kitchens feature custom cabinetry, island dining, and top-of-the-line appliances — ideal for intimate dinners or laid-back entertaining. With central A/C, heating, private laundry, covered parking, and dedicated high-speed fiber internet, no detail has been overlooked.
Outside, a shared resort-style swimming pool, complete with water ledge loungers, hot tub, and a sunken lounge area with a mechanical pergola, offers a private sanctuary under the Key West sun. The swim-up bar and propane grill invite long afternoons of cocktails and conversation, all set against lush tropical landscaping designed with ultimate privacy in mind.

Membership-Style Access to Island House — Without the Crowds

While the Manor shares its enviable location next to Island House, guests enjoy the best of both worlds: private villa living with exclusive access to the 24-hour Island House Café & Bar, where charges can be posted directly to your house account — reminiscent of a private club experience. Unlike the resort, Island Mates Manor is never accessible to the general public, ensuring peace, discretion, and an elevated sense of exclusivity.

Clothing-Optional Freedom and True Gay Hospitality

Island Mates Manor proudly caters to a gay male clientele, offering a welcoming, clothing-optional pool area that reflects the carefree, judgment-free ethos that made Key West famous since the 1970s. When mixed company is present, a visible sign ensures clear, friendly communication. When sign is absent, guests can enjoy the company of fellow men in a relaxed, judgement free environment.

Pet lovers will appreciate the Manor’s dog-friendly policy, with manicured grounds designed for both comfort and privacy. With Island House next door, another renowned LGBTQ+ guesthouse across the street, and the vibrant pulse of Gay Key West all around, Island Mates Manor places you at the heart of it all — yet comfortably removed when you choose to retreat.

The Details
Island Mates Manor | Villas 2 & 3

2 Bedrooms | 2.5 Bathrooms | Split-Level | Sleeps 1-6

Private Pool, Hot Tub, Swim-Up Bar, Near Ocean

Pet-Friendly | Fiber Internet | Covered Parking | Private Entrances

Rates from $464-785/night
28-night minimum stay required
For availability and reservations, visit Island Mates Manor.

Key West is bold, playful, and undeniably proud — now, experience it with the privacy, elegance, and exclusivity you deserve.

www.island-mates.com