by 
Boutique-Style Gay Men’s Guesthouse – King Bed (Bdrm #2 of 7)
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Private room
-
1 guest
-
1 bedroom
-
1 bathroom
-
9 beds
- Clothing optional accepted
- Host shares gay local tips
- LGBTQ+ venues nearby
- Gym nearby or in the property
- Wi-Fi
- Breakfast included
- Dedicated workspace
- Pool
- Hot tub
- Gym
- Parking
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By plugging into weere, the 1M strong LGBTQ+ social hub that boosts your travel experience, you’ll get insider LGBTQ+ tips for your next trip, and connect with new friends, unique community-hosted activities, or even a date - all based on your mood.
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About the Place Initially in English, this text was translated via a machine translation service and may contain inaccuracies or errors.
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.
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.
I have security camera(s) at my place
Amenities
- Clothing optional accepted
- Host shares gay local tips
- LGBTQ+ venues nearby
- Gym nearby or in the property
- Wi-Fi
- Breakfast included
- Dedicated workspace
- Pool
- Hot tub
- LGBTQ+ Kinky Amenities -
Location details and gay map for Orlando
The place is located in Orlando, FL, United States
Exact location disclosed after booking only.
Click below to check the neighborhood and nearby gay places.
Nearby Attractions Initially in English, this text was translated via a machine translation service and may contain inaccuracies or errors.
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
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
Reviews are sorted chronologically, and are not subject to prior monitoring.
More info
Stayed in May 2025
Reviewed on May 10, 2025
So great — I added an extra night!
Response from :
May 11, 2025
So happy you stayed another night, we had a great time and you are welcome back anytime.
Stayed in May 2025
Reviewed on May 09, 2025
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...
Response from :
May 10, 2025
Thank you so jmuch Quincy for the great review and words. You are a true example of the perfect guest. Would certaily like to see you again.
About the Host
Property Rules Initially in English, this text was translated via a machine translation service and may contain inaccuracies or errors.
- Quiet time from 10 PM to 7 AM
- No smoking or vaping allowed on site
- Absolutely no drugs allowed
- No unregistered guests
- Quiet time from 10 PM to 7 AM
- No smoking or vaping allowed on site
- Absolutely no drugs allowed
- No unregistered guests
Check-in:
from
3pm
to
11pm
Checkout:
to
11am
Status:
Business
Licence / registration number:
DWE5926671
Conditions
Extra per guest:
$20 per night after 1 guest(s)
Minimum stay (nights):
1 night
Cleaning fees:
$20 USD
Deposit:
$100 USD
Cancellation Policy
Terms of Services & Privacy Policy apply to this transaction.
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Booking confirmed!
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Agency partner selected by misterb&b
Because we foster the largest community of global gay travelers, we want to ensure all are welcome anywhere we go. Full apartments are in high demand around the world. To help ensure you can travel and feel welcome anywhere, in addition to our gay and gay-friendly hosts, we’ve selected agencies to offer apartments in cities across the world.
Because gay is in our DNA we ask each agency to affirm their welcoming attitude and acceptance of our community by agreeing to the charter below:
Agency Charter
- Checking this box certifies that the management and staff of your agency welcome all people regardless of their sexual orientation or gender identity or expression
- Further, you agree to challenge homophobic and transphobic behavior and ensure a positive and welcoming environment for our guests
- Through a courteous attitude, excluding judgment, your agency will work to ensure a peaceful stay for its LGBTQ+ clientele (information, safety, quality of service and discretion)
Stay like a gay local and feel welcome anywhere you go - misterb&b
Common Questions
What if I have questions about the property before I book?
You can contact Darren and gaetan through the Contact Host button on this page. If you've already booked, go to My trips.
Why should I book through misterb&b?
Travel with peace of mind while connecting with the gay community. As the largest gay hotelier in the world, misterb&b guarantees secure payments, Booking insurance Coverage, and a customer support team that is at your service.
Do I need to pay for a security deposit?
It is up to the host to ask for a security deposit. If there is a security deposit on the listing, the amount is displayed underneath the price per night.
How can I tell if a booking is accepted or confirmed?
A confirmation e-mail with the contact information of your host will be sent to your e-mail address upon a successful booking. Log in to your misterb&b account and visit My trips. Here you will find the status and details of all your bookings and booking requests.
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Agency partner selected by misterb&b
Because we foster the largest community of global gay travelers, we want to ensure all are welcome anywhere we go. Full apartments are in high demand around the world. To help ensure you can travel and feel welcome anywhere, in addition to our gay and gay-friendly hosts, we’ve selected agencies to offer apartments in cities across the world.
Because gay is in our DNA we ask each agency to affirm their welcoming attitude and acceptance of our community by agreeing to the charter below:
Agency Charter
- Checking this box certifies that the management and staff of your agency welcome all people regardless of their sexual orientation or gender identity or expression
- Further, you agree to challenge homophobic and transphobic behavior and ensure a positive and welcoming environment for our guests
- Through a courteous attitude, excluding judgment, your agency will work to ensure a peaceful stay for its LGBTQ+ clientele (information, safety, quality of service and discretion)
Stay like a gay local and feel welcome anywhere you go - misterb&b
With misterb&b, experience a more welcoming world. From gay private rooms and queer-friendly apartments to gay-friendly hotels, gay resorts, and gay vacation rentals, you have the option to stay in the heart of gay districts as well as other neighborhoods in the places you visit. A gay loft in Soho, a shared room with a gay host in Barcelona or the Castro, a gay-friendly hotel in Le Marais, experience misterb&b in all worldwide gay travel destinations! Activate weere on your profile and connect with other misterb&b travelers at your destination city or hotel! Problems with misterb&b? Please refer to our Help Center. And whether you type gay bnb, gaybnb, mrb&b, mister b and b, or misterbandb when you search for us, there's only one misterb&b! misterb&b is not affiliated, endorsed, or otherwise associated with 
, misterbnb, mrbnb, or mr bnb. misterb&b is not a general vacation rental site. Our mission is to connect gay travelers with welcoming hosts. If you’re looking for generic accommodations, we recommend checking other platforms. Site map.
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