NorthNaples

SkyRun Names 2026 Best of Brand Winners

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SkyRun Awarded our Best of Brand Honorees at Our Annual Conference We had a lot to celebrate at the annual SkyRun Conference in Puerto Rico. One of our favorite parts of the conference is honoring our top-performing locations. Each year, our locations partake in a little friendly competition to earn points as part of our … Read more

2026 SkyRun Annual Conference

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SkyRun Locations Gathered in Puerto Rico to Share Ideas and Celebrate Successes This year, we took our annual SkyRun conference to a sunny island locale. SkyRun franchisees and their key employees gathered in San Juan, Puerto Rico with other industry leaders from across the short-term rental space to discuss new ideas, strategies, and tools to … Read more

2026 Short Term Rental Market Outlook

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What the latest market data, regulation changes, and travel forecasts mean for the people who own vacation homes in 2026. The short-term rental industry spent most of the last five years swinging from one extreme to the other. After the pandemic-era boom, the post-boom correction, and a stretch where supply was growing faster than demand … Read more

Understanding Vacation Rental Management Fees and Costs

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When it comes to hiring a short term rental management company, one of the first questions homeowners have is “how much will this cost”? It’s a fair question. Property management fees can look very different from one company to the next, and the industry has not exactly earned a reputation for straight answers. Some companies … Read more

From One Property to Over 1,600 Homes Nationwide

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SkyRun Looks Back on 22 Years of Disciplined, ‘Brick by Brick’ Growth, as the All-American Company Plans and Prepares for Continued Expansion In 2024, SkyRun Vacation Rentals celebrated 20 years in the vacation rental management industry. For the previous two decades, the company remained dedicated to a disciplined, brick by brick, approach to organic growth. … Read more

Understanding Short Term Rental Ownership: What to Know Before Buying a Vacation Rental Property

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Buying a vacation rental property is often seen as the first step to building a real estate portfolio that generates passive income for years to come. With vacation rental usage and ownership surging over the last several years, vacation home ownership is becoming one of the most popular avenues for real estate investing. This guide … Read more

Top Gulf Coast Destinations

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Find the Best Places to Vacation on the Gulf Coast Ready to head to the Gulf Coast for some beach time? With nearly 1,700 miles of U.S. coastline along the Gulf of Mexico, there are so many places to get your toes in the sand, take a dip in the warm water, and hear the … Read more

SkyRun Named Among Top New & Emerging Franchises

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SkyRun is proud to announce we’ve once again been named one of Entrepreneur magazine’s Top New & Emerging Franchises for 2025. Only 150 franchisors earn this distinction each year, and we’re honored to be named among the other successful franchisors who have also earned a spot on this year’s list. As shared by the Entrepreneur team, companies named to … Read more

SkyRun Names 2025 Best of Brand Honorees

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SkyRun awards top-performing locations as part of their Best of Brand Program The time has come to honor the best of the best in the SkyRun family. Our Best of Brand distinction is given to those SkyRun locations who go above and beyond in operating their vacation rental business. To be eligible to win, locations … Read more

Short-Term vs. Long-Term Rentals

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Which is the Best Option for Your Second Home? If you own a second home, chances are you’ve considered renting it as a way to earn extra income. But with that thought comes a lot of questions – first and foremost is whether to rent it on a short-term basis or on a long-term basis. … Read more

The Top U.S. Vacation Spots in 2025

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The Best Destinations to Visit in Every Season of 2025 As we settle into 2025, it’s the perfect time to set your sights on new vacation adventures and dream-worthy destinations. No matter what type of vacation you’re craving – a warm beach escape or a tranquil mountain hideaway – the U.S. has a destination to … Read more

Dynamic Pricing Strategies: How Professional Management Maximizes Your Vacation Rental Revenue

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Owning a vacation rental property is an exciting venture with the potential for significant financial rewards. However, the key to maximizing those rewards lies in one crucial factor: pricing. Setting the right price for your vacation rental is more complex than it might seem. Too high, and you risk deterring potential guests. Too low, and … Read more