Pineapple Acquisitions invests in short-term rentals, multifamily, RV parks, and local businesses — acquiring undervalued assets and building them into high-performing investments.
Pineapple Acquisitions was founded by Tamara Ashworth to bridge the gap between passive investing and active operations. We don't just acquire assets — we improve them.
With deep experience in business operations and strategy, every acquisition is evaluated for its operational upside: Can we streamline? Can we grow revenue? Can we build something that lasts?
That hands-on, systems-first approach is the Pineapple difference.
We operate across real estate and small business acquisitions, always with a hands-on approach.
Acquiring and operating vacation rentals in Charleston, SC — optimizing for occupancy, guest experience, and consistent cash flow in a high-demand market.
Investing in multifamily assets in the Charleston market. Repositioning units, improving operations, and building long-term equity through hands-on management.
Acquiring RV parks and Section 8 housing outside of Charleston — stable, recession-resilient asset classes with strong demand fundamentals and operational upside.
Buying established Charleston-area businesses and installing operational systems to increase efficiency, revenue, and long-term profitability.
Every deal goes through our framework to ensure alignment with long-term goals.
Source off-market and undervalued opportunities where operational improvements can unlock significant upside.
Implement systems, streamline operations, and make strategic investments that increase the asset's performance and value.
Hold for the long term. Compound gains through disciplined management and strategic positioning in strong markets.
Pineapple Acquisitions is based in Charleston, South Carolina — one of the fastest-growing markets in the Southeast. We invest locally because we know the neighborhoods, the opportunities, and the people.
From short-term rentals in the historic district to multifamily repositioning across the Lowcountry, our Charleston roots give us a competitive edge that out-of-market investors simply can't match.
For RV parks and Section 8 housing, we look beyond Charleston to markets with strong fundamentals and high demand — always with the same hands-on approach.
Whether you have a property, a business, or a partnership opportunity, book a consultation and we can talk through the fit, timing, and next best step.