$100M+ in Vacation Rentals Acquired for Investors

Vacation Rental Investment Experts in Oregon

Looking to maximize returns with a vacation rental property? Whether you want to buy, sell, or manage a short-term rental in Portland, Mt. Hood, or the Oregon Coast, Simply Vacation Rental Management is your partner in profitable investments.

Scenic cabin on river in Oregon ideal for Airbnb investment

Why Invest in Vacation Rentals in Oregon?

Oregon’s diverse destinations - from mountain escapes to beach retreats to vibrant city stays - make it one of the strongest vacation rental markets in the U.S. With year-round demand from travelers, investors see:

  • Higher Cash Flow compared to long-term rentals

  • Flexible Personal Use of your property when you want it

  • Strong Appreciation in desirable vacation markets

  • Tax Advantages specific to short-term rentals

But success isn’t guaranteed. The difference between a profitable investment and a money pit comes down to management.

Want to know if your property qualifies for higher returns? Our team offers free one-on-one investment consulting.

Full-Service Real Estate Team

Tired of guessing on your vacation rental investment? Simply gives you insider access to Oregon’s top properties, expert management that outperforms self-managed Airbnbs by 20–40%, and an in-house team to handle everything — buy, sell, and scale all in one place.

  • Aerial view of a large red-brown, multi-story house with multiple wooden decks and balconies, surrounded by trees and located near a road.

    In-House Brokerage Services

    Our licensed in-house agents help you buy, sell, or invest quickly and strategically. With full control over the process, we streamline every step and tailor the experience to your goals.

    - Investor-savvy agents

    - Real-time property intel

    - Seamless coordination with our staging, design, and management teams

  • Victorian-style house with white siding and a steep roof, featuring a front porch with stairs, large windows, and surrounded by neighboring buildings at dusk.

    Buying with Simply

    Find the Right Property — Faster

    From second homes to STR investments, we guide you from search to close.

    - Customized property searches

    - Area-specific data + ROI insights

    - STR compliance and permitting help

    - Design and setup with our in-house team

  • Charming Craftsman-style house with blue siding, white trim, and a covered porch with wooden railings. The home features a neatly landscaped yard, a concrete walkway, and a tree in the foreground.

    Selling with Simply

    Sell with Confidence. Sell for More.

    We don’t just list — we maximize value.

    - Free home valuation

    - Professional staging (in-house!)

    - Targeted marketing + listing strategy

    - Closing support from our team

See If You’re a Good Fit

Free Vacation Rental Investment Analysis

Worth thousands — yours free.

Before you buy (or if you already own), we’ll run a comprehensive investment audit — not just a revenue estimate.

  • Local market demand & comps

  • Projected occupancy & nightly rates

  • Amenity recommendations for ROI

  • Regulatory considerations in your area

  • True operating costs & net income projections

Living room with large windows overlooking a forest, containing a sofa, two armchairs, a small black table, a rug, potted plants, and a brick wall.

Takes 2 minutes. No obligation.