The Vacation Home Reinvented: Inside Evermore Orlando Resort

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Just outside the gates of Walt Disney World, Evermore Orlando Resort is redefining what vacation accommodations can be. Developed by Dart Interests and led by President Chris Kelsey, Evermore isn’t just another upscale lodging option. It’s a purpose-built response to the pain points of group travel, from inconsistent rentals and poor service to logistical overload and lack of privacy.

“When we come together with people we enjoy and care about, we most relish the simple and joyful moments of connection,” Kelsey said. “The Evermore Residences are purpose-built to make it as easy as possible for families and friends — especially large groups — to get to the benefits of time well spent together.”

With group travel on the rise — including multigenerational trips, milestone celebrations, and experience-first getaways — the demand for flexible, elevated, and reliable accommodations is growing. According to Skift Research, 31% of U.S. travelers express interest in multigenerational travel. Evermore delivers a hospitality model designed to meet that demand, offering the comforts of a private residence with the polish and predictability of a modern resort. At the heart of this vision is a key figure: the “alphabooker,” or the group’s primary planner.

Below, we explore how Evermore is solving for today’s group traveler, and what it means for the future of residential hospitality.

For many travelers, group vacations come with compromise — unpredictable home rentals, logistical confusion, and limited amenities. Evermore set out to solve these issues from the ground up.

“Our guest experience was shaped by our own vacations,” Kelsey said. “We’ve all been there — that moment when you open the door to the vacation home rental and think, ‘This can’t be it.’ The space is smaller, it’s not as clean, or doesn’t look like the photo — and suddenly your whole trip feels off.”

Evermore eliminates that uncertainty by combining the comfort and scale of a vacation home with hotel-like consistency, quality, and service. “We also solved the security and service problems often associated with renting someone’s personal home,” he added.

The result is a resort built to make togetherness easier and more enjoyable — for families, friends, and large groups alike.

Evermore was designed with one underappreciated traveler in mind: the alphabooker, or the person responsible for planning the entire group getaway.

“There is the natural leader of every group who steps up to wrangle the date, find the location, pick the rooms, collect the money, make the dinner plans for everyone’s needs, and generally make it all come together,” Kelsey said. “The traveler we call the ‘alphabooker’ is a true unsung hero, and our mission is to make their job easier and more fun.”

That mission shows up across the property, from flexible accommodations with multiple primary bedrooms to options for splitting payments and pre-arranging group dining experiences. For groups of 10 or 20, the goal is to reduce complexity and ease the burden on the person coordinating it all.

While Evermore’s design prioritizes functionality — with private pools at every home, family-friendly bunk rooms, and spacious common areas — it also delivers something less common among large-scale vacation rentals in Orlando: an immersive, resort-caliber environment that blends comfort with curated experiences.

“We didn’t reinvent the family vacation,” Kelsey said, “but we reimagined the home, the services, the culinary experience, and all the supporting fun to optimize large groups’ time together.”

The centerpiece of that experience is Evermore Bay, an eight-acre crystalline lagoon with white-sand beaches, paddleboarding, rope swings, and space to relax. “Orlando can be a hectic destination. While the parks can be exhilarating, they can also be exhausting,” Kelsey said. “We designed Evermore to be the antidote to the theme park experience, creating a literal oasis in which our guests can be as active or relaxed as they want.”

To Kelsey’s surprise, the resort’s immersive atmosphere is winning over more than just Disney families. “A material portion of our guests are choosing Evermore over actual beach destinations,” he noted.

The Evermore team considers the property to be the beginning of a new category, not just a one-off experiment. Purpose-built, owned, and operated by real-estate investment and development firm Dart Interests, the resort offers full operational control and a consistent guest experience that’s hard to find in the short-term rental space.

“Real connection happens when everyone — friends, family, kids, grandparents — gets what they need from the same trip,” said Kelsey. “We built Evermore to eliminate the disappointment and compromise and allow our guests to just enjoy the special moments that become core memories.”

With 13 dining venues, 36 holes of golf, and a slate of curated activities, the resort is more than a place to stay. And services like “Evermore to Your Door” — featuring in-residence four-course meals paired with a mixologist — elevate the experience further.

“We don’t want [guests] thinking about cooking or cleaning. We want them to be immersed in connecting with each other. Let us do the rest,” Kelsey said.

Evermore has also joined the Hilton Honors program, giving guests the chance to earn and redeem points while enjoying the benefits of a true resort stay. “Joining Hilton Honors has been a game-changer,” Kelsey said. “It allows more options for guests and access to the amenities they’ve come to expect.”

For a growing number of travelers, that combination of flexibility, consistency, and immersive design is proving to be the future of group travel. “We are reimagining what it means to stay — and play — together.”

Don’t miss Chris Kelsey in conversation with Rafat Ali at Skift Global Forum, September 16–18. Reserve your spot today.

For more information about Evermore Orlando Resort, click here.

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