Proptech Innovator Roofstock Launches Short-Term Rental Management Division With Investment in Casago

Business Wire

19-05-2025

BUSINESS WIRE)-- Roofstock, a leading platform for investing in and managing single-family rental (SFR) homes, announced its participation in the investor consortium that took Vacasa, Inc. private on May 1. As part of the transaction, Roofstock has secured an ownership stake in Casago, the merged entity, and will officially enter the short-term rental management business by launching Casago franchises in three popular travel destinations:
This strategic expansion reflects Roofstock's commitment to delivering a unified platform of proprietary data and institutional-grade tools for real estate investors of all sizes to research, acquire, manage, and optimize rental properties—whether long-term or short-term.
'Today is an exciting day at Roofstock and for our industry. Historically, we have focused on providing end-to-end real estate investment services for the SFR industry across the ownership lifecycle; from buying to managing to selling. We are excited to extend this suite of products and tools to the massive short-term rental sector, and we couldn't be more excited to partner with Casago,' said Gary Beasley, co-founder and CEO of Roofstock.
By partnering with Casago's franchise network, Roofstock will extend its Rental Genome™ powered tools, such as automated underwriting, home mapping and real-time portfolio intelligence, as well as Stessa, its asset management and accounting software, to the short-term rental sector—simplifying the owner experience and enhancing returns for investors.
'Our initial markets of Tampa, Charleston, and the Oregon Coast each enjoy strong tourism dynamics and robust demand. We look forward to working with short-term rental investors to help them optimize the performance of their homes while providing exceptional experiences to our guests,' said Doug Brien, president of Roofstock and co-Founder of Mynd, which merged with Roofstock last year.
Roofstock has appointed Craig Rashkow to lead its short-term rental division. Rashkow brings deep experience across short-term and long-term rental operations, having held leadership roles at several innovative real estate and hospitality companies, including Sonder and Summer. With a background in scaling high-performing service organizations that leverage modern technology tools, he brings a unique perspective to the convergence of SFR and STR strategies.
'We're pioneering the integration of single-family and short-term rentals with the technology investors need to participate in a cohesive and data-driven way,' said Rashkow. 'Having worked across both asset types, I've long believed that unifying them is a critical next step for the industry and for investors. Roofstock is uniquely positioned to lead this evolution—and I'm thrilled to help make it happen.'
Debt financing to support Roofstock's investment in this transaction was provided by Coromandel Capital.
'Coromandel is proud to support Roofstock in expanding its platform into the STR space. This marks a natural evolution in the convergence of SFR and STR models, and we believe Roofstock – armed with a best-in-class technology platform, unparalleled data insights, deep operational expertise, and a premier property management platform – is uniquely positioned to lead this transformation. We are excited to back a team that shares our vision for modernizing real estate investment infrastructure,' said Alex Wu, Co-Founder at Coromandel.
About Roofstock
Roofstock's mission is to Reinvent the Rental Housing Ecosystem for the Benefit of all. Its platform empowers investors of all sizes to buy, sell, and manage residential investment properties with confidence. Roofstock's platform combines data-driven insights, integrated property management, and a nationwide footprint to dramatically simplify real estate investing. The company has helped facilitate over $9B of transactions, currently manages over 20,000 rental homes, and empowers 300,000+ owners to more efficiently manage over 1M units with its Stessa asset management software. Roofstock has been helping revolutionize real estate investing since 2015, and is backed by a world-class group of investors including Softbank, Khosla Ventures, Bain Capital Ventures, Lightspeed Venture Partners, QED Investors and Invesco.
About Casago
Casago is a top-rated vacation rental management company providing professional property management services for homeowners across North America, Belize, Costa Rica and the Caribbean. Founded in 2001 by former Army Ranger Steve Schwab, Casago has earned a reputation for delivering exceptional guest experiences and reliable property management services through a franchise-driven model. In 2025, Casago expanded its footprint by acquiring Vacasa, a leading vacation rental platform in North America. With a customer-centric approach, the combined company empowers local teams to provide personalized, responsive support for both homeowners and guests. Casago's commitment to quality is reflected in its industry recognition: it is the only property management company of its scale to be rated in the Top 1% by Comparent. Additionally, nearly 95% of U.S.-based local operating partners are Airbnb Superhosts, VRBO Premier Partners, or both.
Founded in 2019, Coromandel is a solution-oriented partner providing bespoke, non-dilutive senior secured capital solutions to leading FinTech, specialty finance, and tech-enabled Companies. Coromandel thrives in the unconventional and esoteric across the corporate Lifecycle. Coromandel provides investors with access to innovative, uncorrelated opportunities with its meticulously constructed portfolios.