Finance and Legal Operations

By Vinicius da Luz Souza, CHAE | 9/21/2026

When we talk about professionalizing the short-term rental industry, the conversation tends to focus on guest experience, dynamic pricing, and channel management. These are legitimate priorities. But there is a structural problem that most operators are not yet addressing—one that affects every financial decision, every conversation with owners, and every attempt to benchmark performance: We do not have a shared language for money.

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By Hal Conick | 7/13/2026

Unpredictable weather is a threat for vacation rental operators everywhere. And they need to start thinking about how they can handle imperfect conditions when, not if, they arise. Of the many levers that can be pulled—making cancellation policies more flexible, investing in guest experience teams, buying cancellation insurance products, to name a few—it's imperative that the planning starts before the bad weather hits.

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By Generali Global Assistance | 12/8/2025

Generali Global Assistance reflects on VRMA Last Vegas, sharing insights from its sessions on travel protection being part of property managers’ business strategy and disaster preparedness, while reminding property managers to review product offerings and refresh team training ahead of the busy holiday season.

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By George Meshkov | 10/6/2025

October is more than a seasonal transition for property managers—it’s a time to regroup, evaluate partnerships, and prepare for the year ahead. A strong travel protection partner offers year-round account management, training, guidance and attach rate support that directly impacts revenue and guest satisfaction.

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By Michele Fitzpatrick | 5/5/2025

Understanding the complexities of hospitality accounting is key to ensuring your short-term vacation rental business stays compliant, efficient, and primed for growth.

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By George Meshkov | 4/7/2025

In Generali Global Assistance’s most recent article, we explore the importance of travel protection and weather preparedness for the vacation rental industry. The article highlights key resources like the Vacation Rental Toolbox, hurricane and winter storm kits, and our upcoming wildfire kit.

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By Caitlin Foster | 3/24/2025

The vacation rental market is growing, but new tax laws and stricter regulations are making compliance more complex for property managers. From evolving marketplace tax policies to rising competition from extended stay hotels, staying informed and automating tax management will be key in 2025.

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By Hal Conick | 2/4/2025

Mastering budgeting, leveraging data, and seeking expert advice have enabled vacation rental businesses to achieve sustained growth and long-term success in a rapidly expanding market.

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11/25/2024

In this episode of the VRMA Arrival podcast, Matthew Gurley, director of sales and partner integrations at Lynnbrook, discusses the growing issue of credit card fraud in the vacation rental industry and the strategies property managers can implement to protect themselves.

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By Jacobie Olin | 11/6/2024

Are you a short-term rental owner looking to build long-term success? Whether you’re managing a growing portfolio or preparing for a lucrative sale, the key is to begin with the end in mind. Planning your exit strategy early on will help you stay focused, maximize profits, and streamline your operations. Below are the top strategies for vacation rental owners—focusing on valuation, benchmarking, and preparing for the future.

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