In the world of hospitality, where comfort meets experience, the art of creating memorable stays is mastered only by those who truly understand the essence of travel. From serene escapes to family getaways, travelers today seek more than just a place to stay—they seek a connection, a story, and a sense of belonging that turns a simple vacation into something unforgettable.
At the forefront of this vision stand Jeff Bosson, Director of Owner Acquisitions; Jonah Mechanic, Vanessa Neff, and Brian Bosson, Owners and partners of SunnyDays Vacation Rentals. Together, they have built a company rooted in integrity, innovation, and a genuine passion for hospitality. With a portfolio spanning California’s finest destinations and beyond, SunnyDays Vacation Rentals represents its shared commitment to quality experiences, outstanding service, and long-term relationships with both guests and homeowners.
Growth Driven by Experience and Innovation
SunnyDays Vacation Rentals was officially founded in 2022–2023, but its leadership team has a long history of collaboration in the vacation rental industry dating back to 2009. Originally, Jeff Bosson and his brother Brian were involved in SeaBreeze Vacation Rental Management, which started with Jonah and Vanessa managing coastal properties in Southern California, growing from a single home in La Jolla to about 50 properties through hard work and partnership. Jeff Bosson transitioned from insurance sales at his brother’s encouragement, contributing to quick growth in Orange County by securing many new homeowners.
As Jeff Bosson explains, “Seeing this potential, Brian made a bold offer: he would pay me my insurance salary for one year so I could focus on growing the business, with the option to return to insurance if it didn’t work out. We took the gamble, and within a year, we managed over 50 homes.” The company eventually grew to oversee more than 420 properties across multiple California regions, including San Diego, Orange County, Los Angeles, Temecula, and Malibu.
In 2020, Sea Breeze was acquired by Vacasa. However, following the acquisition, many loyal homeowners and employees felt disconnected from the new management structure. This led the original founders to re-establish their values under a new brand, SunnyDays Vacation Rentals, in early 2023.
“SunnyDays is our second company, built on experience and a commitment to continuous growth and improvement,” Brian explains. With that accumulated knowledge, they built stronger internal systems, improved service models, and focused on sustainable expansion.
Since then, SunnyDays has expanded from Palm Springs and Temecula into diverse destinations such as Turks and Caicos, Nashville, Ventura, Oxnard, Santa Barbara, and the Central Coast. Each step of growth has been grounded in the principles of operational excellence, innovation, and trust.
Overcoming Growth and Regulatory Challenges
Sustaining growth in the vacation rental industry requires more than securing properties; it demands operational alignment, regulatory awareness, and credibility with homeowners. For SunnyDays Vacation Rentals, managing this balance has been one of its most critical undertakings.
Jeff Bosson views sales as a craft built on trust rather than persuasion. “Sales, in my opinion, is an art—not everyone can do it well,” he notes. Finding individuals who can build long-term relationships with homeowners remains one of the company’s biggest challenges. Equally important is ensuring that what is promised to homeowners can be delivered operationally. Rather than overextending, the company focuses on sustainable expansion supported by strong internal systems.
Launching SunnyDays was more efficient than building the first company, largely because of lessons from Sea Breeze. Processes were thoughtfully designed from the beginning, and past operational gaps were avoided.
Reflecting on earlier challenges, Brian recalls the impact of the pandemic: widespread uncertainty, dramatic fluctuations in travel demand, and growing regulations. “One of the most significant challenges we faced…was navigating the uncertainties brought on by the pandemic.” Those experiences became the foundation for building a more resilient and adaptable organization.
Regulatory pressure continues to influence business decisions. Local laws vary widely, and compliance demands both focus and diplomacy. “Regulatory uncertainty remains a constant challenge,” Brian acknowledges. To address this, SunnyDays actively engages with municipalities and supports policies that balance community interests with responsible vacation rental management.
SunnyDays Vacation Rentals: A Culture of Excellence and Care
- Multiple Locations: Desert, wine country, So Cal Desert, Santa Barbara, Turks and Caicos, coming soon to Texas and Montana
- Property Types: Wine country estates, family homes with pools/spas, romantic cottages, spacious rentals for groups
- Booking Perks: Book direct, best rates guaranteed, expert reservation agents, loyal returning guests
- Homeowner Support: Digital marketing, dynamic pricing, booking management, housekeeping & maintenance scheduling
- Areas Served: Sequoia National Forest, Turks and Caicos, Temecula, California Coastal, Palm Springs & surrounding cities, Texas (soon)
Balancing Scale and Local Care for Success
SunnyDays Vacation Rentals has distinguished itself by combining the reach of a large company with the attentiveness of a local operator. This balance—between scale and local presence—is at the core of its success.
Jeff Bosson believes that operational excellence begins with occupancy. “We have found that balance,” he says when describing the company’s ability to consistently fill calendars while maintaining homeowner confidence. SunnyDays operates across multiple regions, yet ensures each location is supported by an on-site office led by a partner. This structure strengthens accountability and fosters genuine relationships with homeowners and local service teams.
The company’s central office supports each location with advanced technology, marketing, and organizational resources, allowing teams on the ground to focus on property care and guest satisfaction.
Brian stresses that what sets SunnyDays apart is not only growth but execution. While competitors often prioritize digital tools and booking platforms, SunnyDays invests heavily in the fundamentals: housekeeping, maintenance, linen care, and rapid issue resolution.
“Our strength lies not only in doing these tasks well but also in scaling them across multiple cities.”
Repeatable systems and disciplined operations allow the company to deliver consistent standards, whether in a coastal villa, wine-country estate, or desert retreat. The company’s philosophy is simple: scale means little if the basics are overlooked.
Commitment to Exceptional Homeowner Care
Jeff Bosson values the freedom SunnyDays Vacation Rentals has to go the extra mile in caring for its homeowners. He explains that every Monday, the owner services team reviews the upcoming calendar to identify homeowners visiting their properties that week. The team ensures the homes are spotless and in excellent condition, often adding special touches like a bottle of champagne for birthdays or special occasions to show appreciation for the homeowners’ trust. Jeff states, “One aspect I value most about our company is the freedom we have to do whatever it takes to care for our homeowners.”
Brian underscores that while the company has hosted hundreds of thousands of guests, its true strength lies in caring for the homeowners who trust the company with their valuable assets. He notes that many homeowners who previously managed their properties themselves now enjoy peace of mind and improved earnings by partnering with SunnyDays, allowing them to focus on their own vacations and work. Brian concludes, “Ultimately, I’m most proud of how well we take care of our homeowners and their homes.” This dedication to homeowner care is a core part of their service philosophy.
Recognized Success and Focus on Quality Service
SunnyDays Vacation Rentals’ most significant achievement is its rapid growth and ability to scale effectively, a feat few companies achieve at this pace. In 2024, the company was honored by Hospitality Business Review as one of the top 10 vacation rental management companies in America, a recognition that affirmed its strong industry position.
Brian explains that their focus is not on seeking awards or industry recognition. Instead, he emphasizes the company’s dedication to managing and maintaining homes exceptionally well and being a strong partner in the vacation rental industry. Brian states, “While we don’t have specific awards to name, we prioritize day-to-day operations and delivering excellent service in a challenging market.” Their commitment remains rooted in operational excellence and strong partnerships rather than seeking accolades.
Exploring Partnerships and Growth Opportunities
SunnyDays Vacation Rentals purchased Barefoot Vacation Rentals in Temecula in 2023.
Moreover, during its time operating as Sea Breeze, the company acquired one management firm. Jeff Bosson notes they are open to similar opportunities in the future, especially as their non-compete agreement in the California coastal region is ending soon. This will allow them to explore partnerships or acquisitions in those former key markets to support further growth. He adds that, at present, there is nothing specific to disclose.
Brian shares that SunnyDays has formed strategic collaborations, including working closely with a smaller reservation management platform. The company collaborates with the platform’s developers to create software that benefits its internal operations, homeowners, and guests. About a year and a half ago, it acquired a small company in Temecula, California. Although SunnyDays is primarily focused on building the business rather than acquisitions, Brian confirms they remain open to partnerships and collaborations that support their growth plans.
Adapting to Market Saturation and Guest Preferences
“Looking ahead to 2025 and beyond, one challenge SunnyDays anticipates is a sell-off in regions that became oversaturated during the post-COVID boom.” Jeff Bosson addresses. The surge in vacation rental purchases during that time was driven by unprecedented demand, which many believed would continue indefinitely. Now that rates and occupancy have returned to pre-COVID levels, some owners are not seeing the returns they need to justify holding their properties.
He predicts significant sell-offs in areas like Palm Springs and Nashville starting in 2026, though the market will eventually stabilize. To address this, SunnyDays has scaled its operations to effectively manage properties that continue to perform well while supporting those that may be struggling. Jeff Bosson also mentions that major platforms like Airbnb and VRBO are investing heavily in AI to improve bookings and guest satisfaction, and SunnyDays plans to adopt AI technologies that deliver real benefits, carefully testing new tools and discarding those that do not add value.
Brian adds that post-COVID, the vacation rental market saw a large influx of participants, but now some areas are experiencing contraction. He emphasizes that quality inventory — well-maintained homes offering good value — will always be in demand and consistently booked. At SunnyDays, the focus is on popular coastal destinations such as Turks and Caicos and central California, which attract strong travel interest, especially from East Coast guests. Brian notes a positive shift in guest behavior, with longer stays and more family travelers replacing party groups. He expects this trend to continue shaping the industry in the coming years.
Personalized Service with a Human Touch
Brian emphasizes that at SunnyDays, every guest interaction is handled by a real person without the use of AI bots. He states, “We believe direct human contact is essential for effectively addressing guest feedback, whether it’s praise or criticism.” The company employs advanced reporting systems developed from its previous experience to track overall performance. While individual issues do occur, they are addressed quickly and personally in real-time. Their main goal is to consistently provide a high-quality experience across thousands of checkouts annually.
SunnyDays focuses on the key concerns of both guests and homeowners by closely monitoring trends. If any negative patterns emerge, it conducts thorough investigations to identify the root causes, resolve the problems, and move forward. Rather than chasing every minor issue or new technology fad, SunnyDays responds promptly to significant concerns with transparent communication and effective solutions. This practical approach helps it continuously improve while maintaining trust and satisfaction at the core of its service.
Creating a Positive, Process-Driven Workplace
SunnyDays’ company culture is something Jeff Bosson stresses the importance of. He explains that when they relaunched the company, they brought back key employees from Sea Breeze who had embraced its culture. Each department has three clear, realistic goals that it prioritizes to ensure smooth operations. The team holds weekly Work In Progress (WIP) meetings every Tuesday to review performance and discuss challenges openly. Its culture focuses on processes—when issues arise, they analyze the breakdown, adjust accordingly, and avoid recurrence. Jeff Bosson emphasizes that in a logistics-heavy business like theirs, reliable processes and consistent execution are critical, and this focus on clear goals, open communication, and continuous improvement forms the heart of SunnyDays’ culture.
Brian stresses the value of office culture, noting that while some employees work remotely, most collaborate closely in a shared office space. His teams—including guest experience, dispatch, owner services, and accounting—work near each other to promote integration and teamwork. Brian believes office culture shapes the company’s behavior, communication, and reputation. They prioritize hiring top talent who thrive in a positive, non-toxic environment where everyone motivates each other to improve. While technology supports bookings, marketing, and communication, the core of their business is hands-on daily operations. Focused meetings and company-wide accountability help maintain strong values, team spirit, and leadership at SunnyDays.
Open Letter: Advice for Aspiring Leaders and Entrepreneurs in Hospitality
Jeff Bosson’s (Director of Owner Acquisitions) message for the readers,
My key advice is to avoid over-leveraging. Many newcomers try to start companies by purchasing and managing multiple homes at once. If the market takes a downturn, this approach can quickly unravel. Instead, scale intelligently—grow slowly and efficiently, adding processes and employees as needed, but not prematurely.
At SunnyDays, we often ask: “Is this a one-off sound bite or a real trend?” For new entrepreneurs, it’s crucial to focus on long-term trends rather than reacting to fleeting noise. Pay attention to what’s consistent and meaningful to build a sustainable business.
Brian Bosson’s (Co-owner and Partner) message for the readers,
My key advice for those entering the hospitality industry, especially in managing other people’s assets, is to focus on doing the essential, often unglamorous tasks exceptionally well and consistently. Trust is earned by maintaining a very low failure rate in the basics—whether it’s ensuring laundry arrives on time, or homes are cleaned thoroughly.
Many try to do too much and overlook these fundamentals. Running a vacation rental business means managing thousands of cleanings, handling large volumes of laundry, and supplying homes reliably. Excelling at these basics is critical.
At the same time, it’s important to stay aware of new trends and innovations. You can do both—master the essentials while looking ahead. Keep your operations simple and focused, and continuously improve the core aspects that keep your business running smoothly every day.
5 Key Takeaways from SunnyDays Vacation Rentals’ Journey
- Values First: Leadership rooted in trust, integrity, and personal relationships.
- Built on Experience: Past lessons shaped smarter systems and sustainable growth.
- Excellence in Basics: Success driven by mastering operations, not just technology.
- Scale with Care: Expanding widely while maintaining local, hands-on service.
- Resilient Mindset: Adapting to regulations, market shifts, and industry challenges with long-term vision.
