Skift Global Forum Video: Breaking the Vacation Rental Mold

This sponsored content was created in collaboration with a Skift partner.

Orlando is synonymous with theme parks, from Walt Disney World to Universal Studios. For decades, hotels there have leaned on proximity to rides and conference halls, rarely standing alone as destinations. At Skift Global Forum in New York, Chris Kelsey, president of Dart Interests, joined Skift CEO Rafat Ali on stage to explain how Evermore Orlando is changing that narrative.

The $900 million resort — anchored by a Conrad Hotel, a Caribbean-style beach, and 13 food and beverage outlets — positions itself as the area’s first true destination resort. Its standout feature is the Evermore Residences: multi-bedroom vacation homes paired with hotel-level services, designed for families, friend groups, and milestone gatherings.

“You don’t hear of anybody going to a resort in Orlando and spending five days,” Kelsey told Ali. “But that’s exactly what Evermore is.”

Kelsey sees Evermore as a new category in the market: a comprehensive resort where guests can arrive, settle in, and stay put. He pointed to the artificial beach as a centerpiece that is better “than the pictures” and supports a full slate of activities, dining, and relaxation.

Early feedback from guests suggests the strategy is working. “Over half of our guests are coming to us because they’ve chosen Evermore over an actual beach destination,” Kelsey said. That choice reflects confidence that the resort itself delivers the leisure experience people want, even in the middle of central Florida.

Hilton’s partnership on the Conrad Orlando strengthens the offering, plugging Evermore into Hilton Honors’ global loyalty ecosystem. Kelsey credited Hilton with “an absolutely awesome job running the hotel” and emphasized the value of their collaboration in shaping the broader resort experience.

According to Kelsey, the real innovation lies in the Evermore Residences. Ranging from four to 11 bedrooms, these vacation homes are designed for group travel, but unlike a traditional rental property, they include hotel services, 24/7 gated security, and built-in design features that simplify logistics.

Kelsey framed the concept as an answer to friction in group travel: “How do we create a better guest experience that gets you to what you came for, which is to connect with your family and friends, faster? That was the goal.”

Instead of leaving large groups to navigate kitchen logistics, bedroom privacy, or bill splitting, Evermore engineered solutions from the start. Guests can pre-arrange grocery delivery, rely on on-site activities, and use digital tools like a “split the bill” function. “We tried to come up with ways to make the alpha booker’s life a lot easier,” Kelsey explained, referring to the person who usually takes on the thankless job of organizing multi-family trips.

By removing friction, Evermore frees guests to focus on the social experience — whether that’s a Disney visit, a family reunion, a wedding, or a corporate retreat.

If the residences are the hardware, the underlying operating system is connection. Kelsey called Evermore an “antidote to the theme park experience,” a place where guests can “drop your shoulders and relax and connect, as opposed to being in the frenzy.”

That philosophy dovetails with a larger cultural shift. In 2023, the U.S. Surgeon General declared loneliness a public health epidemic. Travel brands have increasingly sought ways to respond, often through solo wellness offerings like sleep optimization or spa treatments. Evermore flips the focus outward, coining a new term: “relational wellness.”

“What we’ve learned from our guests is that because we created this experience where it’s easy to connect with family and friends, they’re leaving with a sense of rejuvenation,” Kelsey said. “We really believe that creating health through connection is more valuable than any massage you’ll ever get or any supplements you’ll ever take.”

This positioning moves wellness beyond the individual, embedding it into group design and resort programming.

Evermore Orlando may be the first of its kind, but Dart Interests has no intention of stopping there. “We are actively on the hunt for both mountain destinations and beach destinations,” Kelsey said, noting that the company is ready to invest further after the initial $900 million in Orlando. The aim is to replicate the Evermore model in markets with “low seasonality” and strong air access, bringing the group-first, wellness-through-connection ethos to other travel environments.

This expansion ambition hints at a broader play: a portfolio of Evermore resorts that compete not only with theme park hotels but also with high-end vacation rentals and luxury all-inclusive resorts. By combining scale, services, and shared experiences, Evermore could carve out a new hospitality category.

For now, Evermore’s tech presence is modest. The resort operates a mobile app, which Kelsey admitted “is mediocre” but on the verge of being replaced. He acknowledged AI’s potential in hospitality but said the company is still exploring it. His “dream of an AI concierge” reflects his awareness that seamless digital support will be critical in scaling Evermore’s high-touch model.

What stands out is not tech itself, but how Evermore has aligned design, operations, and service delivery to reduce stress points for group travelers. The tech stack will eventually need to match that ambition, but the guest experience already signals a step change.

For the hospitality industry, Evermore’s model illustrates several converging trends:

• Group Travel Growth: Multi-generational and multi-family trips are rising, with travelers seeking shared yet flexible accommodations.
• Wellness Redefined: The shift from individual treatments to “relational wellness” opens new storytelling and product opportunities.
• Hybrid Hospitality: Residences with hotel services blend rental appeal with branded reliability.
• Destination Creation: Resorts can become stand-alone draws even in competitive markets.

In Kelsey’s words, Evermore is a “better mousetrap for a group travel experience.” Its timing — in a cultural moment hungry for connection — may be as important as its design.

For more information about Evermore Orlando Resort, click here.

This content was created collaboratively by Dart Interests and Skift’s branded content studio, SkiftX.