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. We are also a clothing-optional so you can have the freedom to relax as you please. 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.
Our Property
Pineapple Harbor is 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. 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.
Our Story
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 unwind, make new friends, and enjoy your time.
We strive to be more than just a place to stay. Hosting brings us immense joy and we’re excited to make your visit memorable and enjoyable. We look forward to making you feel right at home!
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