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HHC invests in vacation rental manager VTrips

Hudson Hill Capital has made an investment in VTrips, a Florida-based vacation rental manager.

Hudson Hill Capital has made an investment in VTrips, a Florida-based vacation rental manager. VTrips expects to deploy over $250 million in the near-term to acquire vacation rental management companies.


JACKSONVILLE, FL, August 12, 2021 – VTrips, a Florida based technology-enabled vacation rental manager throughout North America, announced today that it received a significant minority equity investment from Hudson Hill Capital (“HHC”), with all capital being funded to the balance sheet. VTrips will leverage the investment to accelerate the company’s acquisition strategy and to further strengthen its technology offering. VTrips expects to deploy over $250 million in the near-term to acquire attractive vacation rental management companies.

Founded in 2002 by CEO Steve Milo, VTrips offers full-service vacation rental management, including digital marketing, coupled with local market operations to service and maintain vacation properties, with the majority of its inventory in the Southeast today. VTrips’ mission is to deliver a superior financial outcome and concierge-level experience to its property owners while simultaneously delivering a better and differentiated vacation experience to travelers.

Steve Milo, founder and CEO of VTrips, commented, “Our new investors have placed a significant vote of confidence in our vision, our people and our technology that will further enhance the customer experience. This investment, combined with Hudson Hill’s track record of scaling businesses like ours will help us extend our market leadership through a carefully designed acquisition strategy that will further build our category defining technology and service offering. VTrips possesses a very promising future.”

According to Eric Rosen, Managing Partner of Hudson Hill, “Steve has built VTrips into the leading independent vacation rental management platform and one of only a select number of operators with a multi-state footprint. Perhaps more notable about VTrips is its proven ability to operate effectively and profitably over multiple decades. HHC is excited to partner with Steve during the company’s next phase of growth and to use our collective experience to help build the company’s footprint both organically and through M&A, capitalizing on the tailwinds within the growing vacation rental market.”

According to Mr. Milo, “This significant investment represents another key milestone for our company as the vacation rental resort market in North America continues to boom, especially in drive-to markets, and there is far more demand than supply which has resulted in a more than 20% increase in Average Daily Rates in many markets. Covid-19 accelerated the adoption of vacation rentals over hotels and the sector also benefited significantly from social distancing, remote work and remote learning which allows more flexibility for travel.”

VTrips already completed three acquisitions in the first half of 2021, most recently acquiring Panama City, FL-based Resort Collection with close to 800 units. The Resort Collection deal follows several other acquisitions in the Southeast region, including Distinctive Vacation Rentals in Fort Myers Beach, Florida and Resort Properties in Pigeon Forge, Tennessee. The company has completed over 20 acquisitions since its founding.

The vacation rental industry is very fragmented yet, according to Mr. Milo, owners of smaller property management companies are increasingly concerned about who they sell to. “We are encountering more and more sellers who want a buyer that will hire all their staff, take care of their brand and legacy, and allow them to live in their community with pride. With this capital infusion, we are poised to accelerate our activity as a buyer and represent a unique landing place for an independent vacation rental operator.”

About VTrips
Located in Ponte Vedra, Florida, VTrips manages 3,000 exclusive vacation rental properties in traditional resort destinations ranging from Florida to Hawaii. VTrips CEO and founder Steve Milo is a recognized thought leader regarding the evolution of the highly fragmented vacation rental industry and is a regular keynote speaker at leading conferences in North America and Europe. For more information, visit

About Hudson Hill
Based in New York, HHC ( is a private investment firm founded by Eric Rosen, Jason Palmatary, and Alexander Stacy. Departing from the prevailing short-term orientation of the private equity industry, HHC invests with families, entrepreneurs, and management teams who are attracted to patient, long-term capital partners. Hudson Hill invests its own capital alongside like-minded partners in attractive growth-oriented opportunities in industries benefiting from long-term secular growth tailwinds. HHC’s industry focus includes the business services, software, and financial services sectors.