Skift Podcast Compelling discussions with travel industry leaders and creatives who are helping to shape the future of travel. Compelling discussions with travel industry leaders and creatives who are helping to shape the future of travel. Learn More

As the line between short-term rentals and hotels continues to blur, Dart Interests is betting that the next generation of resorts won’t choose sides. In a new episode of the Skift Travel Podcast, Skift CEO Rafat Ali sat down with Dart President Chris Kelsey to explore the company’s $2.5 billion flagship project—Evermore Orlando—and a bold vision for hybrid, group-first hospitality.

Located next to Walt Disney World, Evermore is different than many other resorts in the market: a master-planned destination that combines luxury vacation homes with traditional hotel rooms, all managed under one umbrella and anchored by a 433-room Conrad. The idea, according to Kelsey, is to solve the pain points of both legacy hotels and short-term rentals while meeting the needs of modern families and multigenerational travelers.

“We didn’t want to retrofit homes into hospitality,” Kelsey said. “We designed everything from the ground up for this exact use case—groups, gatherings, and consistent hotel-level service.”

Listen to This Podcast

Apple Podcasts | Spotify | YouTube | RSS

Bridging the Gap Between Hotels and Rentals

At the core of Evermore’s model is what Kelsey calls “residential hospitality.” Unlike Airbnb or Vrbo, none of the homes are privately owned or inconsistently managed. All units—from 2-bedroom flats to 11-bedroom homes—are owned, operated, and serviced by Dart Interests, offering the scale of vacation rentals with the standards and loyalty benefits of a hotel.

That alignment with Hilton Honors is a key differentiator. Evermore is the first property where Hilton has integrated non-traditional units—like villas and vacation homes—into its global loyalty ecosystem.

“You can now book an 8-bedroom house with Hilton points,” Kelsey said. “That’s transformational, not just for us, but for travelers who are looking for more space without giving up quality or perks.”

An “Anti-Theme Park” Philosophy

While Evermore sits next to one of the busiest tourist corridors in the U.S., Dart intentionally designed it as a counterpoint to the high-energy, high-saturation theme park experience.

“Everything in Orlando goes fast, flashes lights, or tries to entertain you,” Kelsey said. “We wanted the opposite—calm, open spaces, human-scale architecture, and intentional landscaping that helps people decompress.”

That focus has helped Evermore attract not only park-goers but also destination weddings, reunions, and corporate retreats. The crown jewel is an eight-acre crystalline lagoon that serves as both centerpiece and recreational hub, surrounded by event venues, cabanas, and casual dining.

Rethinking Food, Labor, and Landscape

Dart Interests is also challenging conventional resort operations. After encountering difficulties running 13 food and beverage outlets in-house, the company partnered with Chicago-based Lettuce Entertain You to bring culinary expertise and brand consistency to the portfolio.

Landscaping and maintenance have also been rethought from scratch. With more than 1,000 acres under management, Dart has internalized many traditionally outsourced services to ensure long-term quality and cost control.

And on the labor side, Kelsey emphasized Dart’s investment in building a stable, full-time workforce rather than relying on contractors or gig labor.

“Hospitality isn’t just about the physical product—it’s the people delivering the experience every day,” he said.

Building for the Long Game

Unlike many resort developers chasing yield and flipping assets, Dart is taking a long-term ownership view. Kelsey says the firm’s privately held structure allows it to prioritize brand equity, operational resilience, and guest satisfaction over short-term gains.

“What we’re building with Evermore is not meant to be sold in five years,” he said. “It’s a forever asset—and that changes how you design, staff, and operate.”

Looking ahead, Dart is exploring expansion into mountain, lake, and coastal markets, using the Evermore playbook to serve group and family travelers often underserved by traditional hotels or vacation homes.

But Kelsey is clear: this isn’t about scaling fast. It’s about scaling right.

“We don’t want to copy and paste Evermore,” he said. “We want each location to feel grounded, local, and thoughtfully built for how people actually travel—and stay—today.”