Strategic Real Estate
Investment

DJay Holdings LLC acquires, renovates, and repositions residential properties across the country — creating value in every deal we touch.

4–8
Week Rehab Timeline
4
Exit Strategies
Nationwide
Markets Served
Who We Are

Built on Integrity.
Driven by Results.

DJay Holdings LLC is a real estate investment company focused on acquiring undervalued properties, executing high-quality renovations, and creating value in the communities we work in — nationwide, with a strong presence in the Florida / Orlando area and active projects beyond. Full about page →

Dana Cowles, Co-Founder and Principal of DJay Holdings LLC
Co-Founder & Principal

Dana Cowles

Dana is an Emergency Medicine Physician, public speaker, and business coach whose drive extends well beyond the clinic. A self-described recreationally terrible poker player, he brings sharp analytical thinking and a passion for smart investing to every deal DJay Holdings pursues.

dana@djayholdings.com
Jason Cowles, Co-Founder and Principal of DJay Holdings LLC
Co-Founder & Principal

Jason Cowles

Jason brings a creative eye and entrepreneurial spirit forged through years in fashion and retail. As the owner of Don't Slip Just Drip — his own clothing line — he knows what it takes to build a brand from the ground up. Off the clock, you'll find him in the kitchen, where his passion for cooking matches his appetite for a great deal.

jason@djayholdings.com
What We Do

Our Investment Strategies

Fix & Flip

We identify distressed properties below market value across the country, execute strategic renovations, and sell at a premium — all types of deals considered.

  • Purchase below market value
  • Quality rehab in 4–8 weeks
  • FSBO + MLS dual strategy

Learn more →

Short-Term Rentals

We acquire and reposition properties in high-demand tourism and travel markets nationwide, partnering with Evolve to maximize occupancy and nightly rental income.

  • High-demand travel markets
  • Evolve management partnership
  • Optimized nightly pricing

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Long-Term Rentals

We acquire and hold residential properties as long-term rentals, building a stable income-generating portfolio while providing quality housing in the communities we serve.

  • Stable monthly cash flow
  • Buy-and-hold strategy
  • Residential & multi-family

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Wholesaling

We source deeply discounted off-market properties and connect them with the right buyers — moving deals quickly and efficiently without the need for renovation.

  • Off-market deal sourcing
  • Fast contract assignments
  • No rehab required

Learn more →

Portfolio

Our Current Properties

From mountain short-term rentals to active rehab projects — experience DJay Holdings in the field.

Short-Term Rental
Maggie Valley · Blue Ridge Mountains, NC
5.0 · ~41 reviews

Bonnie View 21

~3,000 sq ft mountain retreat featuring stunning views, two decks, a hot tub, and a fire pit. Minutes from Cataloochee Ski Area, Great Smoky Mountains National Park, and Asheville. Book through Evolve and major vacation platforms.

Hot TubFire Pit2 DecksMountain Views~3,000 Sq Ft
Recently Acquired Exterior of 4019 W Muhammad Ali Blvd, Louisville KY — front porch at dusk
Front exterior at dusk Front exterior daytime Front elevation Listing photo 4 Listing photo 5 Listing photo 6 Listing photo 7 Listing photo 8
West End · Louisville, KY 40212

4019 W Muhammad Ali Blvd

Classic 1925 craftsman bungalow with a wide brick-pillared front porch and ~1,725 sq ft across 4 bedrooms and 2 baths. Recently acquired by DJay Holdings — full renovation in progress. Near Shawnee Park with convenient downtown access.

4 Bed2 Bath~1,725 Sq FtBuilt 1925Rehab in Progress
Network

Trusted Partners

Local expertise that helps us move faster on acquisitions and renovations.

REALTOR® Partner

Dave Gambol

simpler.realestate · Louisville, KY & Southern Indiana

Louisville-area realtor partnering with DJay Holdings on acquisitions — clear, investor-friendly guidance through every stage of the deal.

KY License 270336
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Rehab / Construction Partner

J. Clark Baird

Louisville Investment Property LLC

Louisville rehab and construction partner supporting DJay Holdings renovations — maximizing value with clean, modern finishes while controlling materials, labor, and hold costs.

Louisville, KY
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Guest Reviews

What Our Guests Say

5.0 · ~41 reviews · Bonnie View 21
“This home is absolutely beautiful and very spacious! Waking up to the beautiful Mountain View every morning was incredible. It was perfect for our family.”
Sarimar MillerJun 2026
Airbnb
“This house was everything listed and more! Everything you could possibly need is furnished. The beds and pillows were wonderful! The view from the decks was amazing!”
Dawn TrentMay 2026
VRBO
“The home was cozy and well kept. Everyone had a wonderful time on the adjustable beds. The cabin was well stocked… This place was fantastic!!!! We loved it.”
Jesse WiseMay 2026
VRBO
Get In Touch

Let's Work
Together

Whether you have a deal to share, a question about what we do, or just want to connect — we'd love to hear from you. Reach out and we'll be in touch shortly.

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