The Future of Direct Bookings with Phil Kennard of FutureStay

Independent hosts are the backbone of the short-term rental industry—but many are still building their businesses on someone else’s platform. If that’s you, you’re not alone. But it’s time to think bigger.

In this week’s episode of Thanks for Visiting, we sit down with Phil Kennard, the founder of FutureStay, a direct booking platform designed specifically for what he calls “rental-preneurs.” These are hosts who want more freedom, more control, and more profit from their properties—but without the complexity of traditional PMS systems.

Phil shares:

• How he went from accidental host to building software for 100,000+ hosts
• Why over 90% of short-term rental hosts manage five or fewer properties
• What FutureStay does differently from property management software
• How to optimize your Airbnb listing with his “48-point checklist”
• Why even a few direct bookings can completely change your profitability
• The key to building trust with guests in what he calls the “trust recession”

We also talk about how hosts can legally nurture guest relationships even under Airbnb’s new off-platform policy, what the “billboard effect” is, and how to show up on Google Vacation Rentals as your official website—not just a link back to a big OTA.

If you’re ready to stop guessing and start building a more profitable, independent hosting business, this episode is a must-listen.

Download a transcript of this episode.

Resources:

• FutureStay | Direct booking platform for rental-preneurs (exclusive offer for TFE listeners)
• Google Vacation Rentals | Where 70%+ of travel searches begin
• Airbnb’s Off-Platform Policy | New rules effective May 2024
• Proper Insurance | STR insurance designed for hosts
• The Hosting Handbook | Your beginner’s guide to starting strong

#STRShareSunday

@cornerstonecottage_acadia

Looking for a peaceful coastal escape with views that make you pause? Cornerstone Cottage is a serene retreat near Bar Harbor and Acadia National Park that blends refined interiors with rustic charm and shoreline beauty.

From the wraparound porch to the wood stove and private firepit, every inch of this four-bedroom, 2.5-bath home invites you to slow down and soak it in. Ocean views, Acadia’s mountains in the distance, and shoreline access make it a rare find for families or groups wanting comfort and connection to nature.

We love how this host has created a space that’s just as ideal for a cozy morning coffee as it is for launching a day of coastal adventure.

Explore more at @cornerstonecottage_acadia or book your stay here.

We would love to feature YOU! Submit your property for our next #STRShareSunday at strshare.com.