Scaling With Intention: Inside the Rise of Rather Be Properties

Built from the perspective of owners first, Rather Be Properties has grown into a multi‑market vacation rental brand by prioritizing design, data, and hands‑on leadership over volume. Elissa and Al Sedighravesh credit their expansion to disciplined systems, AI‑assisted insights paired with human oversight, and a deeply personal approach to owner and guest relationships. In a post‑pandemic landscape defined by higher expectations and tighter margins, their strategy is clear: hospitality, technology, and accountability working in lockstep to create sustainable, high‑performing homes across every market they serve.

Elissa & Al, you’ve grown Rather Be Properties from a small portfolio into a multi-market vacation rental company — can you share how that journey started and what’s driving this current expansion phase?
Rather Be Properties started very organically. Al and I began as owners ourselves — not with the intention of building a large management company, but with the goal of creating beautiful, high-performing vacation homes that we would personally want to stay in.

As we expanded into markets like Orange County, Palm Springs, San Diego, Big Bear, Arizona, and the Outer Banks, other owners began asking if we could manage their homes the same way we managed ours. That demand — driven by results — is what sparked the growth of Rather Be Properties.

What’s driving this current expansion phase is infrastructure and intentional scaling. Over the years, we’ve built a full-time team that supports operations, guest communication, marketing, and revenue management. We’ve also developed internal systems and integrated A.I. tools that allow Rather Be Properties to operate seamlessly across multiple states without losing the personalized touch we’re known for.

We’re not expanding just to add doors — we’re expanding strategically, partnering with owners who want professional, data-driven management backed by real oversight.

The vacation rental industry has shifted significantly post-pandemic — what changes are you seeing most clearly, and where do you think owners are getting it right or wrong right now?
Post-pandemic, the vacation rental industry has moved from rapid expansion to professionalization.

At Rather Be Properties, we’re seeing that demand has normalized, competition has increased, and guest expectations have risen significantly. During the surge years, occupancy was easier. Today, it requires strategy.

The owners getting it right are:
• Investing in design and quality furnishings
• Understanding dynamic pricing
• Treating their property as a true business

Where some get it wrong is relying solely on automated pricing tools without human oversight, resisting necessary price adjustments, or underestimating the importance of five-star reviews.

At Rather Be Properties, we combine market data, A.I.-assisted analytics, and hands-on revenue strategy to ensure our homes remain competitive while protecting long-term profitability.

As a boutique, hands-on management company, how do you differentiate yourselves from larger corporate firms while operating across multiple states?
Rather Be Properties sits in a unique position — we’re boutique in service but structured in operations.

We have a dedicated full-time team supporting guest communication, operational coordination, marketing, and performance tracking. At the same time, Al and I remain directly involved in strategy, revenue oversight, and owner relationships. Our owners have direct access to us — not a call center.

We’ve invested heavily in systems:
• A.I.-assisted guest communication for fast, consistent responses
• Automated workflows for turnovers and maintenance coordination
• Revenue dashboards tracking performance across markets
• Direct booking infrastructure to reduce third-party dependency
• Standard operating procedures across every location

These systems allow Rather Be Properties to operate efficiently across multiple states while still delivering personalized, hands-on service.

Larger firms may rely on volume. We rely on strategy.

What does it really look like behind the scenes to run a family-owned, husband-and-wife real estate business, especially at this scale?
Behind the scenes at Rather Be Properties, it’s structured, data-driven, and team-oriented.

Al focuses on financial performance, investment strategy, systems development, and owner communication. I lead guest experience, branding, and marketing. Our full-time team executes daily operations across all markets, ensuring consistency and accountability.

We review booking pace, ADR trends, seasonality shifts, and market data regularly. We refine listings, adjust pricing, evaluate amenities, and optimize operations constantly.

A.I. supports communication speed and operational coordination, but decisions are always reviewed with human insight.

Being family-owned means accountability. Our name is on the business, and our reputation matters deeply. That level of ownership drives everything we do.

With increasing regulations and competition, what strategies are you using to help property owners maximize profitability while maintaining a strong guest experience?
At Rather Be Properties, sustained profitability comes from operational discipline, strategic pricing, and consistent guest experience — not short-term rate spikes.

We focus on five core pillars:
1. Active, daily revenue management — combining data, A.I. tools, and human oversight.
2. Multi-platform distribution plus a strong direct booking strategy.
3. Strategic amenity investments that justify higher ADR and increase booking appeal.
4. Operational efficiency through systems and automation to protect margins.
5. Review optimization and guest experience consistency.

Profitability today isn’t about charging the highest nightly rate — it’s about balancing occupancy, reputation, and operational control.

Rather Be Properties was built on the philosophy that hospitality, technology, and strategy must work together. The owners who succeed in this next phase of the industry are the ones who embrace all three.