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PrideGay Hotels
Boutique-Style Gay Men’s Guesthouse – King Bed (Bdrm #2 of 7)
Boutique-Style Gay Men’s Guesthouse – King Bed (Bdrm #2 of 7)
Darren and gaetan
Response rate: 100% • Response time: < 1h
Happy to share local tips

Boutique-Style Gay Men’s Guesthouse – King Bed (Bdrm #2 of 7)

Orlando, FL, United StatesLGBTQ+ venues nearby•Map
Exceptional5.0(12)Booked 12 times
Private room
1 guest
1 Bedroom
1 Bathroom
9 beds
Clothing optional acceptedHappy to share local tipsLGBTQ+ venues nearbyGym nearby or in the propertyWi-FiBreakfast includedDedicated workspacePoolHot tubGymParking

The Reveal

Near LGBTQ+ SceneCozyGreat for Fitness LoversInsta-WorthyRelaxingCentral location

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.

How the beds work

Bedroom #11 King Size Bed
Bedroom #21 Queen Bed
Bedroom #31 Queen Bed
Bedroom #41 Queen Bed
#1 Shared space2 Bunk beds
#2 Shared space3 Bunk beds

Little Luxuries

Clothing optional accepted
Happy to share local tips
LGBTQ+ venues nearby
Gym nearby or in the property
Wi-Fi
Breakfast included
Dedicated workspace
Pool
Hot tub
The Classics
Wi-Fi
Dedicated workspace
Kitchen
Pool
Breakfast included
Air conditioning
TV
Terrace
Washer
Essentials
Hair dryer
Dishwasher
Dryer
Iron
Heating
Hot tub
Outdoor dining area
Parking
Sound system
Netflix
LGBTQ+ Favorites
LGBTQ+ venues nearby
Happy to share local tips
100% gay
Adult Only
Gym
Gym nearby or in the property
Welcome
Clothing optional accepted
Fire protection
Smoke alarm
Fire extinguisher
LGBTQ+ Kinky Amenities

Meet Your Proud Host

Darren and gaetan
5.0(32 reviews)
E-mail verifiedPhone verifiedID verified
Member sinceAug. 2023
Response rate100%
Response time< 1h
My partner and I share a love for travel, exploration, and making connections with people from all walks of life. We’re passionate about creating a warm, inviting space where guests can feel at home and enjoy a truly memorable stay. When we’re not hosting, we love spending time at the cottage, entertaining family and friends, and exploring new destinations. Whether you’re here for relaxation, adventure, or just a change of scenery, we’re here to help make your visit special. We look forward to welcoming you to our home and sharing the joy of great hospitality!
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10 interests: Environment / Movies / TV Shows / Dance & Electro / Disco / Latin Music / New wave / Camping / Horseback riding / Motor sports

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October 2026
SMTWTFS
November 2026
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Why Book Proud with misterb&b?

Travel with purpose. Support the LGBTQ+ community with every stay.
Your discretion is guaranteed
Your invoice and bank statement never show "misterb&b".On your statement:PinkLab
Every stay gives back to the community
This booking will contribute to our Mister for Good program, helping LGBTQ+ NGOs around the world.
Built by and for the LGBTQ+ community
We're an LGBTQ+-owned platform. Your support directly funds jobs and livelihoods for our LGBTQ+ team.
Unlock the local gay scene
Meet LGBTQ+ locals with weere, discover insider tips and explore beyond your hotel.

Where It's All Happening

Orlando, FL, United StatesExact location disclosed after booking only.
LGBTQ+ Safety Score: Orlando
5out of 5Very safeRated by 12 local misterb&b members

Nearby Attractions

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

House Rules & Conditions

Check-infrom 3pm to 11pm
Checkoutto 11am
Host recommendations

- Quiet time from 10 PM to 7 AM - No smoking or vaping allowed on site - Absolutely no drugs allowed - No unregistered guests

Extra per guest$20 per night after 1 guest(s)

$20 per night after 1 guest(s)

Minimum stay (nights)1 night

1 night

Cleaning fees$20 USD

$20 USD

Deposit$100 USD

$100 USD

Licence / registration numberDWE5926671

DWE5926671

Cancellation Policy

Terms of Services & Privacy Policy apply to this transaction.

Add dates to get the cancellation details

ReviewsExceptional5(12)

Reviews come from verified guests, are sorted chronologically and not subjected to prior monitoring.

Cleanliness5.0
Location5.0
Accurate description5.0
Check-in5.0
Value for money5.0

Our Community Has Spoken:

JohnStayed in November 2025
Reviewed on Nov. 15, 2025

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.

Response from Darren and gaetan
Nov. 16, 2025

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.

CraigStayed in May 2025
Reviewed on May 26, 2025

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!

Quincy DionStayed in May 2025
Reviewed on May 10, 2025

So great — I added an extra night!

Response from Darren and gaetan
May 11, 2025

So happy you stayed another night, we had a great time and you are welcome back anytime.

Quincy DionStayed 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 ... BOOK!

Response from Darren and gaetan
May 10, 2025

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.

EricStayed in April 2025
Reviewed on Apr. 28, 2025

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.

Response from Darren and gaetan
Apr. 30, 2025

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!

RickStayed in April 2025
Reviewed on Apr. 17, 2025

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.

Response from Darren and gaetan
Apr. 30, 2025

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!

ScottStayed in March 2025
Reviewed on Mar. 30, 2025

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.

StevenStayed in March 2025
Reviewed on Mar. 23, 2025

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.

Response from Darren and gaetan
Mar. 24, 2025

Thank you Steven for the review. Hope to see you soon. All my best!

JustinStayed in March 2025
Reviewed on Mar. 19, 2025

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!

Response from Darren and gaetan
Mar. 20, 2025

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.

AdamStayed in February 2025
Reviewed on Feb. 23, 2025

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!

Response from Darren and gaetan
Feb. 23, 2025

Thank you for the taking the time in reviewing your stay, its much appreaciated and you are welcome anytime at our Guest House. Cheers!

Exceptional5.0(12)