With a commitment to inclusivity, diversity, and supporting LGBTQ+ causes,
Prideaway Stays enhances the vacation rental experience for both homeowners and guests.
We are the only official members of the Airbnb Experienced Co-Host program exclusively
serving Provincetown Hosts, using specialized tools to provide listing management services.
With a commitment to inclusivity, diversity, and supporting LGBTQ+ causes,
Prideaway Stays enhances
the vacation rental experience for
both homeowners and guests.
We are the only official members of the Airbnb Experienced Co-Host program exclusively serving Provincetown Hosts,
using specialized tools to provide listing management services.
Prideaway Stays homes appeal to Provincetown visitors of all types, recognizing and valuing the quality homes that we expertly manage.
Prideaway Stays homes appeal to Provincetown visitors of all types, recognizing and valuing the quality homes that we expertly manage.
24/7 Guest Communication
Rest easy! Late-night calls from guests are a thing of the past. We manage all communication before and during their stay.
Cleaning &Laundry
Finding a cleaner in Provincetown is not easy, especially during the summer. Leave it to us and our extensive network! We hire, train, and coordinate with cleaning professionals.
Repairs + Maintenance
From squeaky beds to water leaks and overgrown lawns, we work with local maintenance professionals to ensure your Provincetown property is always in impeccable condition.
Revenue + Occupancy Management
Many DIY hosts do not understand how to optimize nightly rates. National companies often cut rates and charge extra fees to guests. We're experts at how to utilize transparent, dynamic pricing.
Ongoing Listing Optimization
In the ever-changing landscape of Airbnb and Vrbo, we persistently tweak and refine your listing, aiming for prime placement on the first page of Provincetown search results for your occupancy.
Custom Digital Guidebook
Questions from guests are expected, and we're here to help. We design a unique guidebook for your property, elevating the guest stay and proactively answering their potential questions.
Repeat Guests
Your best customers are those who have already stayed with you. We can set up processes to keep in touch with past guests via email and social media and encourage future rebooking.
Direct Booking Sites
Having a dedicated site for your property is a game-changer. We specialize in crafting and managing a site where guests can book directly, enjoying savings by avoiding unnecessary fees.
24/7 Guest Communication
Rest easy! Late-night calls from guests are a thing of the past. We manage all communication before and during their stay.
Cleaning + Laundry
Finding a cleaner in Provincetown is not easy, especially during the summer. Leave it to us and our extensive network! We hire, train, and coordinate with cleaning professionals.
Repairs + Maintenance
From squeaky beds to water leaks and overgrown lawns, we work with local maintenance professionals to ensure your Provincetown property is always in impeccable condition.
Revenue + Occupancy Management
Many DIY hosts do not understand how to optimize nightly rates. National companies often cut rates and charge extra fees to guests. We're experts at how to utilize transparent, dynamic pricing.
Ongoing Listing Optimization
In the ever-changing landscape of Airbnb and Vrbo, we persistently tweak and refine your listing, aiming for prime placement on the first page of Provincetown search results for your occupancy.
Custom Digital Guidebooks
Questions from guests are expected, and we're here to help. We design a unique guidebook for your property, elevating the guest stay and proactively answering their potential questions.
Repeat Guests
Your best customers are those who have already stayed with you. We can set up processes to keep in touch with past guests via email and social media and encourage future rebooking.
Direct Booking Sites
Having a dedicated site for your property is a game-changer. We specialize in crafting and managing a site where guests can book directly, enjoying savings by avoiding unnecessary fees.
Brian
July 2024
Christine
May 2024
Jason was the best host - immediately responsive, even from his own vacation. His digital app, the guidebook, and even the little signs around the house ensured we never had any questions. We felt very cared for.
Travis
June 2024
Kirsten
July 2024
Jesse
July 2024
Elizabeth
July 2024
Since 2016, Jason has had the privilege of hosting memorable guest experiences for thousands of travelers, including their
furry companions, in beautiful and comfortable vacation rentals.
He's one of the very few 30x Airbnb Superhost and 28x Vrbo Premier Host!
Originally from just north of
New York City, Jason has called Boston and its surroundings home for 20 years,
he brings a profound understanding of
the region's unique spirit and allure.
Ethan is an experienced Superhost, demonstrating a deep appreciation for vacation rentals, both as a guest and host. As a globetrotter, he values returning to serene, well-maintained accommodations after full days of exploration.
His interests encompass sports, music, and the joy of discovering fresh destinations with loved ones. Ethan is an avid globetrotter, constantly seeking out new places to enrich his global adventures, all while showcasing his remarkable talent as a classical cellist.
Rory Gill, a skilled real estate attorney and broker, infuses his expertise into the inner workings of Prideaway Stays. Combining Jason's extensive hospitality experience with Rory's legal acumen and real estate insights, the duo provides a unique blend
of care and professionalism.
Jason and Rory are dads to their lovely
and spunky daughter Cecily, who loves making friends and taking pictures
all over Provincetown!
Since 2016, Jason has had the privilege of hosting memorable guest experiences for thousands of travelers, including their furry companions, in beautiful and comfortable vacation rentals.
He's one of the very few
30x Airbnb Superhost and
28x Vrbo Premier Host!
Originally from just north of
New York City, Jason has called Boston and its surroundings home for 20 years, he brings a profound understanding of the region's unique spirit and allure.
Ethan is an experienced Superhost, demonstrating a deep appreciation for vacation rentals, both as a guest and host. As a globetrotter, he values returning to serene, well-maintained accommodations after full days of exploration.
His interests encompass sports, music, and the joy of discovering fresh destinations with loved ones. Ethan is an avid globetrotter, constantly seeking out new places to enrich his global adventures, all while showcasing his remarkable talent as a classical cellist.
Rory Gill, a skilled real estate attorney and broker, infuses his expertise into the inner workings of Prideaway Stays. Combining Jason's extensive hospitality experience with Rory's legal acumen and real estate insights, the duo provides a unique blend of care and professionalism.
Jason and Rory are dads to their lovely and spunky daughter Cecily, who loves making friends and taking pictures all over Provincetown!
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87 Reviews
4 guests | 2 bedrooms | 2 beds | 1 bathroom
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48 Reviews
6 guests | 2 bedrooms | 3 beds | 2 bathrooms
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6 Reviews ( New Listing )
2 guests | 2 bedrooms | 2 beds | 1 bathroom
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8 Reviews ( New Listing )
4 guests | 1 bedroom | 2 beds | 1 bathroom
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4 Reviews ( New Listing )
6 guests | 3 bedrooms | 5 beds | 2 bathrooms
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4 Reviews ( New Listing )
4 guests | 2 bedrooms | 2 beds | 2.5 bathrooms
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1 Review ( New Listing )
4 guests | 2 bedrooms | 2 beds | 1 bathroom
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( New Listing )
4 guests | 2 bedrooms | 2 beds | 1 bathroom
For years, our founders have owned properties outside of Provincetown and have hosted thousands of guests!
While we're not currently offering vacation rental co-hosting services in these regions,
we're genuinely proud of these homes and have chosen to include them in our portfolio
to provide a richer perspective of our diverse experiences.
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39 Reviews
14 guests | 4 bedrooms | 8 beds 4 1 bathroom
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116 Reviews
6 guests | 2 bedrooms | 3 beds | 2 bathrooms
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44 Reviews
10 guests | 4 bedrooms | 7 beds | 3.5 bathrooms
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132 Reviews
8 guests | 4 bedrooms | 5 beds | 2.5 bathrooms
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38 Reviews
4 guests | 2 bedrooms | 3 beds | 1 bathroom
✓ Competitor identification
✓ Pricing analysis
✓ Amenities + Features
✓ 12-month revenue forecast
✓ Property improvement recommendations (when necessary)
✓ Physical space setup
✓ Listing creation + optimization
✓ Coordinate professional photos and videos
✓ Messaging automation
✓ Digital guidebook creation
✓ 24/7/365 guest communication
✓ Cleaning + maintenance management
✓ Crisis + dispute resolution
✓ Quality assurance
✓ Supply + inventory management
✓ Dynamic pricing
✓ Guest rebooking
✓ Facebook advertising
✓ Cross-listing promotion
✓ Influencer partnerships
I confirm that I want to receive information from Prideaway Stays using the contact information that I provide.
Whenever possible, we partner with Provincetown businesses, artists, and local events.
Every stay with us supports LGBTQ+ rights, equality, and community events.
We support the Provincetown and LGBTQ+ communities by giving a portion of our net proceeds - meaning after all owner payouts - back to causes near and dear to our hearts.
The Real Estate Law Podcast
Jason and Rory bring together top advisors and real estate professionals from across the country, exploring a wide range of topics, including real estate trends, passive income, financial independence, short-term rentals, real estate syndications, legal marketing, building your brand, commercial real estate, multi-family investing, the investor mindset, and much more.
At Prideaway Stays, we're more than
co-hosting vacation rentals.
Whenever possible, we partner with Provincetown businesses, artists,
and local events.
Every stay with us supports LGBTQ+ rights, equality, and community events.
We support the Provincetown and LGBTQ+ communities by giving 5% of our net proceeds - meaning after all owner payouts - back to causes near and dear to our hearts.
Navigating Provincetown's Seasonal Rental Market: Strategies for Success
Like many beach communities, Provincetown is a highly seasonal market.
Have a walk down Commercial Street on a Wednesday in the winter, and you won’t...
When people visit your home in Provincetown, are you welcoming them with scratchy towels, mismatched dinnerware, and uncomfortable mattresses? Here are ways to level up your...
At Prideaway Stays, our founders are also Provincetown Second Homeowners. We’re your neighbors, your guides, and your partners in making your property more than a short-term rental, but a retreat that..
The Real Estate Law Podcast
Jason and Rory bring together top advisors and real estate professionals from across the country, exploring a wide range of topics, including real estate trends, passive income, financial independence, short-term rentals, real estate syndications, legal marketing, building your brand, commercial real estate, multi-family investing, the investor mindset, and much more.
I confirm that I want to receive information from Prideaway Stays using the contact information that I provide.
We also often use StayFi wireless routers which allow us to legally collect guest contact information for marketing purposes.
We believe in simple and transparent pricing.
Set-up and Tech Fees (typically $1,500-2,750): This covers all the upfront work required to get a property prepped and ready for optimal performance. This may include travel, physical space prep, coordinating professional photography and video content, listing creation, direct booking set up, social media setup, ad preparation, on-site technology installation, and miscellaneous start-up activities.
Booking Management Fee (22-28% of gross rental income, depending upon the property and personal usage): Our business model is designed to align with your success – we only earn when you do. This mutually beneficial arrangement motivates us to work collaboratively to ensure your rental property thrives. We'll carefully monitor booking revenue and provide you with a monthly invoice.