Discover Pineapple Harbor Guesthouse
Our Property
Our Property
Our Property
Welcome to Pineapple Harbor, an exclusive men's guesthouse catering to gay and bisexual guests. Here, you'll find safe, stylish, and unique boutique-style accommodations in a sophisticated and relaxed resort setting. Our property boasts beautifully designed themed rooms, a large private pool, a hot tub, and even a dark room for your pleasure, all set within an inviting atmosphere. Additionally, we are a clothing-optional guesthouse, allowing you the freedom to relax as you please. Located in a highly sought-after gated community just 3 miles from Walt Disney World and other major attractions, Pineapple Harbor is also a short Uber distance from Orlando's vibrant gay bars and nightlife. Experience the perfect getaway for a memorable and enjoyable stay.
Our Story
Our Property
Our Property
As hosts with a passion for discovering new destinations and experiences, we noticed during our travels a lack of dedicated spaces where gay and bisexual men could feel truly safe and comfortable. That’s why we created Pineapple Harbor—to offer a welcoming retreat where you can relax, connect with others, and enjoy your time.
We strive to be more than just a place to stay; we want to be a space where you can unwind and make new friends. Hosting brings us immense joy, and we’re excited to make your visit memorable and enjoyable. We look forward to welcoming you and helping you feel right at home!
Our Services
Our Property
Our Services
At Pineapple Harbor Guesthouse, we go above and beyond to ensure our guests have everything they need for a comfortable and memorable stay. Our charming guesthouse offers both private and shared rooms to suit your preferences.
Enjoy our complimentary snacks and refreshments, available throughout your stay. Additionally, join us on our beautiful lanai on Mondays, Wednesdays, and Fridays from 6 PM to 7 PM for a delightful meet-and-greet with your hosts and fellow guests.
Contact us today to learn more about Pineapple Harbor Guesthouse and start planning your perfect getaway!