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Best Short Term Rental Property Management & Consulting

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Serving Short Term Rental Owners / Investors
Chicago, IL, 60657
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Running a short-term rental should feel like a smart investment—not a second job. Whether you’re managing one unit or a portfolio of properties, Best Property Management brings the experience, systems, and service mindset to help your rentals perform consistently and profitably.

We work with individual homeowners, investor groups, and short-term rental operators to deliver hospitality-level service with an owner-first strategy. From automated guest communication and calendar sync to on-the-ground turnover coordination and dynamic pricing, we manage every detail to maximize revenue and protect your property—all while delivering five-star experiences that drive repeat stays.


What Makes Us Different:

  • We speak the language of both investors and guests. We optimize for revenue while caring about reputation, guest experience, and long-term asset health.

  • Not just tech—real support. We combine smart automation with local, hands-on management, so things don’t fall through the cracks.

  • Custom strategies for every owner. From single-unit vacation homes to regional portfolios, we design a tailored plan that aligns with your market, goals, and vision for the future.

  • Built to grow with you. Whether you’re scaling up or streamlining operations, our systems are built for efficiency at every stage—so your short-term rentals don’t outgrow your management.

  • Local compliance experts. We keep your properties in line with short-term rental laws, city requirements, and evolving licensing rules.

  • Financial performance you can see. Live dashboards, monthly reporting, and data-driven recommendations help you understand exactly how your property is performing.


Thinking About Stepping Away from Self-Management?

Late-night guest issues. Cleaning crew mix-ups. Constant pricing adjustments. If managing your short-term rental feels like a full-time job, we get it.

At Best Property Management, we’re here to help you step back—without stepping away from performance. We bring the systems, responsiveness, and strategy that turn STRs into top-rated, top-grossing investments.


For Professional Operators and Portfolio Investors

If you're a professional operator or investor looking for a management partner to help you scale, we can plug in at any level—operational support, performance consulting, or full end-to-end management.


Our STR Services Include:

  • Dynamic pricing and revenue optimization

  • Guest screening and automated communication

  • Calendar management and OTA platform integration (Airbnb, VRBO, etc.)

  • Cleaning & turnover coordination

  • 24/7 guest support

  • Owner dashboards and financial reports

  • Compliance monitoring and licensing support

  • Property setup, photography, and listing optimization


Whether you own one property or a growing portfolio, we help you get more bookings, better reviews, and stronger returns—without the daily grind.

Let’s talk about how we can make your short-term rental work better for you.

PROPERTY TYPES WE MANAGE
  • Single Home or Condo (Valued up to $300K)
  • Single Home or Condo ($300 to $500K)
  • Multi-Family (2-4 units)
  • Vacation (1-2 units)
  • Vacation (3+ units)