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Property Management Intern

Prideaway Stays
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Paid, High-Impact Summer Internship in Provincetown

Property Management, Social Media & Business Operations Internship with Leading Cape Cod Short-Term Rental Management Company, Prideaway Stays (PAS)

Who We Are: Prideaway Stays is a fast-growing, tech-driven short-term rental management company based on Cape Cod in legendary Provincetown, MA. We optimize luxury properties across Airbnb, Vrbo, and direct channels, currently managing 50+ premier properties and $65M+ in Provincetown real estate assets. As the only official Airbnb Experienced Co-Hosts in P-town, we help owners "Stress Less and Earn More" while delivering 5-star experiences in one of the most exclusive, LGBTQ+-friendly destinations in the world.

Location: On-site presence in Provincetown, MA. Ideal candidates are Cape-based or willing to relocate to beautiful Cape Cod within driving distance to Provincetown for the duration of the summer internship. (We provide a dedicated central workspace/hub in P-town for meetings, admin work, downtime, and parking between property visits!)

Dates: June 1 – August 31, 2027 (Flexible start/end dates available for local candidates interested in starting earlier in May or extending into September).

Pay: $20/hour

Hours: 30–40 hours/week

Schedule: Flexible, with core operational windows spanning 9:00 AM – 6:00 PM. Weekend availability (at least one weekend day) is required during peak season. We will craft a unique schedule that fits you and our business. Past interns have taken their “weekends” on traditional weekdays since much of our business is packed on weekends!

Team Structure: Joining a collaborative Cohort of Summer Interns on the ground in P-town.




 

The Opportunity

Skip the "boring" corporate internship. At PAS, we don't do busywork or coffee runs. You will work alongside a team of fellow interns, a virtual customer service team, and caring management and receive direct mentorship from our founders, gaining real-world experience in high-end hospitality, real estate technology, digital marketing, and entrepreneurship.

We balance field-based operational leadership with behind-the-scenes business education, giving you a complete look at how a multi-million-dollar property portfolio operates.

Key Responsibilities

  • Property Operations & Quality Control: Take ownership of 50+ luxury properties using structured checklists, smart-lock tech (Schlage), and property management software (Hospitable). Ensure 5-star guest readiness, troubleshoot on-site needs during key turnover windows, and master high-stakes property management.
  • Content Creation & Social Media Marketing: Lead our digital presence! Shoot engaging B-roll, capture event coverage across P-town, conduct quick interviews with property owners and guests, and help build our brand across Instagram and TikTok.
  • Guest & Owner Relations: Provide concierge-level support to guests, assist with owner communications, and serve as an active brand ambassador with local vendors and community partners.
  • Business & Real Estate Masterclasses: Gain executive exposure through dedicated learning sessions covering dynamic pricing, real estate investing, STR market analysis, dynamic revenue modeling, and owner financial reporting.
  • Property Knowledge & Documentation: Create visual property reference guides by documenting and photographing key details such as breaker locations, parking, trash bins, linen and supply closets, lockboxes, entry points, and other frequently asked property-specific information.

What We Provide Our Intern Cohort

  • Dedicated Intern Hub: A central base in P-town for team meetings, admin work, scheduled breaks, and guaranteed downtime parking between site visits.
  • Branded Gear & Toolkits: Official Prideaway Stays apparel for professional identification on-site, fully stocked supply kits, and streamlined mobile scheduling tools.
  • Direct Executive Mentorship: Regular check-ins and strategy sessions with our co-founders to discuss market trends, entrepreneurship, and your career goals.

What We’re Looking For

We welcome undergraduate and graduate students from any field of study or major—from business, communications, and hospitality to computer science, psychology, humanities, and beyond. You don't need a background in real estate to thrive here; we care far more about your drive, curiosity, and adaptability than what’s written on your degree transcript.

If you are eager to learn, build real-world skills, and immerse yourself in a fast-paced environment, this role offers hands-on experience across the wide array of industries we inhabit:

  • Luxury Hospitality & Guest Relations — Delivering 5-star concierge experiences and managing premium short-term rental stays.
  • Real Estate & Property Tech (PropTech) — Learning asset management, dynamic pricing models, smart home integration, and property operations for a $65M+ portfolio.
  • Digital Media & Content Marketing — Building brand strategy, content creation, social media growth (Instagram/TikTok), and video production.
  • Entrepreneurship & Small Business Operations — Experiencing the inner workings of a high-growth, venture-minded startup firsthand.
  • LGBTQ+ Tourism & Community Advocacy — Championing inclusive business practices and local commerce in a world-famous, historic community.

Qualifications & Ideal Traits:

  • Transportation & Mobility: Undergraduate or graduate student (Cape Cod locals strongly preferred) with reliable transportation for getting around Provincetown.
  • Mindset: Tech-savvy, resourceful self-starter with a "no task too small" entrepreneurial attitude who thrives in a dynamic mix of active field work and creative office time.
  • Communication: Clear, confident communicator who enjoys collaborating with team members, engaging with local business partners, and interacting with property owners and guests.

Your Mentors

  • Jason Muth: 25+ year media veteran, 36x Airbnb Superhost, and host of the SmartStay Show podcast.
  • Ethan Sobel: Expert in marketing, client relations, and mission-focused leadership with a deep background in STR property operations.

How to Apply

Ready to gain real-world business and hospitality experience in P-town? Submit your resume and a brief cover letter explaining why you’re a great fit for our 2027 Intern Cohort to ethan@prideawaystays.com.

Learn more: prideawaystays.com | IG: @Prideawaystays

Prideaway Stays is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees and interns.