

Welcome to Pineapple Harbor Guesthouse – A Boutique Retreat for Gay Men
Step into a world of elegance, coziness, and relaxation at our newly renovated boutique-style guesthouse—a safe, inclusive, and clothing-optional escape designed exclusively for gay men. Thoughtfully designed for comfort and connection, Pineapple Harbor offers an intimate atmosphere where you can unwind, socialize, and feel at home.
Your Experience Start your morning with a complimentary continental breakfast, then soak up the Florida sun by our private, south-facing pool—perfect for tanning and swimming. Lounge in the hot tub, enjoy a quiet moment with a book, or engage in conversation with other guests in our comfortable outdoor lounge.
On Fridays, we host a social hour on the lanai, where you can mingle with fellow guests over drinks, share travel stories, and enjoy a welcoming atmosphere.
For those seeking a more discreet and intimate setting, we offer The Dark Room—a private space designed for exploration and connection in a respectful environment.
Luxury Amenities At Pineapple Harbor Guesthouse, we focus on comfort and indulgence with: ✔ A comfortable bed you won’t want to get out of ✔ Plush towels for the pool area ✔ Complimentary snacks, coffee, and tea throughout your stay ✔ Shampoo, conditioner, and body wash provided in all rooms ✔ Smart TVs for your entertainment ✔ Extra pillows and blankets available upon request ✔ A beautifully designed outdoor lounge area for relaxation
Ideal Location We are perfectly situated to offer both tranquility and easy access to top attractions: 📍 12 minutes from Walt Disney World 📍 26 minutes from Universal Studios and International Drive 📍 Close to restaurants, shopping, and nightlife—including LGBTQ+-friendly spots
Your Room This listing is for one of our seven elegantly appointed rooms. Your private retreat includes: 🛏 A comfortable, high-quality bed for an unbeatable night's sleep 🚿 A private washroom stocked with premium toiletries 🖥 An in-room office desk available upon request 🚪 A walk-in closet and dresser for ample storage 📺 Cable TV and Smart TV for entertainment
Additional Information 🚗 Parking is limited—please inquire when booking to reserve a spot. A $20+ tax non-refundable parking fee applies per stay. 📹 For security, cameras are installed at the front entrance and pool area only—your privacy is our priority. 🚫 No pets allowed—we maintain a pristine and allergy-friendly environment.
At Pineapple Harbor Guesthouse, we leave no detail overlooked. From our high-end bedding to the thoughtfully designed social spaces, we provide an experience that feels both indulgent and welcoming.
We look forward to hosting you.
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We are 3 miles from Walt Disney World, and close to other major Tourist attractions. Gay establishments are approx. 30 min away by Uber/Lyft: Bars - Hanks Bar, Barcodes Orlando, and Savoy Orlando. Saunas - Club Orlando
- Quiet time from 10 PM to 7 AM - No smoking or vaping allowed on site - Absolutely no drugs allowed - No unregistered guests
$20 per night after 1 guest(s)
1 night
$20 USD
$100 USD
DWE5926671
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Reviews come from verified guests, are sorted chronologically and not subjected to prior monitoring.
I had an awesome time staying here. Gaeten is an excellent host. He welcomed me at the door and from that moment there was great conversation with him and his other guests. I especially enjoyed the location. It was quiet but had easy access to lots of fun locations. To anyone looking for a super clean place to hang your hay for a few days, you can't go wrong here.
Thank you so much for your kind words. It was a real pleasure having you stay with us. I'm glad you enjoyed the location and the conversations with me and the other guests. We always aim to create a comfortable, friendly space for everyone who visits. You were a wonderful guest, and we'd be happy to welcome you back anytime. Safe travels and hope to see you again soon.
Five star weekend getaway in Kissimmee! The host was friendly, communicative, and spent time with us at the pool, making us feel like we were visiting friends. The home was clean, updated, and just as listed. The pool was a highlight! During our stay, we attended a pool party, brunch at Celebration's farmers market, and dinner at Disney Springs. Great location, great vibes — would definitely stay again and highly recommend!
So great — I added an extra night!
So happy you stayed another night, we had a great time and you are welcome back anytime.
To say that this place feels like "home" is an understatement. Walking thru the door, there's an immediate feeling of openness, acceptance, and comfort. I have stayed in folks' homes all over, and I never thought I would find paradise in my backyard. In seeking a local getaway, I found a gem in this place! If any room in the Pineapple Guesthouse is available ... BOOK!
Thank you so much Quincy for the great review and words. You are a true example of the perfect guest. Would certainly like to see you again.
Wonderful space and even better hospitality from Gaetan, who went above and beyond. Will absolutely be my go to spot when I am visiting the Orlando area.
It was great to meet you! I'm so glad you enjoyed your stay. You're welcome back anytime, and I hope to see you again—maybe next time with your partner too!
What a beautiful place to stay. The house is very clean and comfortable. Pool and hot tub area are beautiful. I was able to spend some time with Gaetan by the pool. We had a great visit. He made it a very warm and relaxing stay. Would definitely stay here again. I felt I had made a new friend when I left.
Thank you so much for the kind words, HP! It was truly a pleasure having you stay with us. I'm so glad you felt comfortable and enjoyed the space and I really appreciated the time we spent chatting by the pool. You have such great stories, and it genuinely felt like I was saying goodbye to a new friend. You're welcome back anytime!
What a beautiful place to stay. The house is very clean and comfortable. Pool and hot tub area are beautiful. A really warm welcome and very relaxing stay. Would definitely make this a return visit.
Great place to stay at as it was very clean, had a nice pool and hot tub, room was spacious, bathroom nice, bedding and mattress were very comfortable. Hosts were very welcoming, and I enjoyed their company. I will book here again when I'm back in this area.
Thank you Steven for the review. Hope to see you soon. All my best!
This place is picture perfect with the most gracious and accommodating hosts. It was the perfect relaxation spot after a long work day. Zero complaints and would definitely book again!
Thank you for taking the time in reviewing our guest house. It was great meeting you and we would love to host you again. Zero complaints on our side as well.
My stay here was fantastic! This being my first time booking on misterb&b, I'd definitely recommend staying here! Gaetan was an excellent host, and every detail was well thought out. The location near Disney World was a major plus too. I hope to be back soon!
Thank you for the taking the time in reviewing your stay, its much appreaciated and you are welcome anytime at our Guest House. Cheers!
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