Chris Kelsey, President of Dart Interests, dives into innovative approaches in hospitality with a focus on the Evermore Orlando project. He discusses the fusion of luxury hotels and vacation rentals tailored for families and groups, challenging traditional travel models. Kelsey reveals how loyalty programs like Hilton Honors enhance guest experiences and shares the philosophy behind their ‘anti-theme park’ design. He also explores the push for long-term value in real estate, emphasizing a unique strategy for group travel and expansions into diverse markets.
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insights INSIGHT
Hybrid Resort-Rental Model Insight
Evermore bridges the gap between traditional hotels and short-term rentals with a hybrid model.
This meets family and group travel needs more effectively than either alone.
volunteer_activism ADVICE
Maximize Distribution Channels
Distribute your resort on multiple platforms including your own to reduce commission costs.
Joining loyalty programs like Hilton Honors can boost distribution and recognition.
insights INSIGHT
Anti-Theme Park Design Insight
Evermore embodies an "anti-theme park" ethos by creating a safe, luxurious beach environment away from Orlando's hectic areas.
The resort offers a relaxing oasis that appeals especially to families.
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Skift CEO Rafat Ali talks with Chris Kelsey, President of Dart Interests, about how the firm is pushing the boundaries of what a resort can be. At the heart of the conversation is Evermore Orlando, Dart’s $2.5 billion destination next to Disney World that blends managed vacation rentals with luxury hotels, all designed with families and groups in mind.
Kelsey breaks down why the traditional split between short-term rentals and hotels no longer works for modern travelers and how Evermore aims to fill that gap. He also shares how loyalty plays a central role in Dart’s strategy, especially through its alignment with Hilton Honors, and why they’ve embraced what he calls an “anti-theme park” philosophy when it comes to design.
The discussion spans the evolution of Evermore, Dart’s growing portfolio across mountain and beach markets, and how the company is rethinking fundamentals like food and beverage, landscaping, and labor models. It's a deep dive into what happens when long-term vision, intentional design, and group-first thinking come together to challenge the status quo.
Key themes:
Why Dart is betting big on hybrid resort-vacation rental models
Building at scale for families, groups, and multigenerational travelers
How loyalty programs like Hilton Honors can unlock differentiation
The “anti-theme park” design lens and what it means for experience
Long-term value over short-term yield in real estate and hospitality
Expansion into mountains, beaches, and overlooked secondary markets
Reinventing food and beverage, landscaping, and workforce strategies
Positioning Evermore against Airbnb, hotels, and legacy resorts
The Skift Travel Podcast