Rookie Looking for Creative Financing Receptiveness in Market

Douglas Sullivan · 2026-09-14T06:30:18-07:00

I am interested in getting a beach house that is short term rented. My goal is to do some form of creative financing whether it be seller financed with a DSCR loan, or try to do a lease to own with an eventual mortgage assignment, or some other form of creative manuvre that avoids the steep down payment while also offering a fair compensation to the seller. I am about 10 hours away from the area as well, for what it's worth and how that impacts this analysis How feasible are these ideas? How do people finance short term rentals like a beach house? Am I on the right track? Follow up, if I am on the right track, where are good starting points for building a team? I realize being in town and networking will be the most productive moves.

Douglas, the creative-financing ideas are feasible, but I'd separate "can I structure it?" from "does the STR still work once the financing and operating risk are layered in?"

Seller financing can be a good fit if the seller values steady income, wants to defer receiving all the cash upfront, or has a property that has been sitting. A DSCR loan can also work for an STR, but the lender's treatment of projected rental income, reserves, appraisal, and property type can vary quite a bit.

I’d be more careful with anything involving a lease-to-own or eventual mortgage assignment. Many loans aren’t freely assumable or assignable, and you don’t want a structure that unintentionally creates a due-on-sale issue. I’d have a real estate attorney review that before relying on it.

Being 10 hours away also changes the underwriting. For a beach STR, I'd include full management, cleaning, utilities, maintenance, insurance, flood/wind exposure, furnishing replacement, vacancy, and local STR rules from day one. Creative financing can lower the cash needed upfront, but it doesn't fix weak operating economics.

From the tax side, once the property is placed in service as an STR, depreciation begins. Depending on average guest stay and your material participation, the losses may potentially be treated differently from a normal long-term rental. Cost segregation can also become meaningful, but I'd want the deal to work before relying on the tax benefit.

For the team, I'd prioritize a local STR-focused agent, lender, property manager, insurance broker, inspector, attorney, and CPA before getting too far into negotiations.

Feel free to DM me, I'd be happy to send over a few STR tax resources that might help as you evaluate the deal.

Rookie Looking for Creative Financing Receptiveness in Market

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