Blending Hotels and Rentals: Dart’s Bet for Group Travel at Scale

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

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