Maximize Your Rental Income — Without Maximizing Your Worry

Three Oregon co-founders. Ten years in this state. One mission: hospitality done right.

At Cascadia Getaways, your home is more than an asset on a spreadsheet. We care for every property like it's our own — because for more than a decade, we've built our business practices on the idea that better outcomes for homeowners come from a team that's actually invested in the work. Our co-founders run revenue strategy, owner relationships, and on-the-ground operations themselves. The expertise is in the room, not behind a portal.

Real numbers for your home, not a guess. Response within hours.

Cascadia Getaways By the Numbers

Why Homeowners Choose Cascadia Getaways

Local Expertise. Proven Performance. Hospitality-First Operations.

Cascadia Getaways is Oregon-only and employee-owned. No outside investors. No growth-at-all-costs mandate. No outsourced 1-800 call center. Our incentives are aligned with yours by design — and our team has been doing this together long enough to make it look easy.

1. Revenue strategy from a co-founder who's done it at scale.

When you hire Cascadia, your revenue strategist is co-founder, Ryan Rabideau, Ryan spent years building revenue management algorithms at Vacasa before leaving to build something different in Oregon. He's spoken on the VRMA conference stage about OTA distribution strategy because he’s earned the right to. When a new platform like HomeToGo or Whimstay launches, we already know whether it's worth your home's attention — and how to get you premium placement when it is.

That's the difference between a property manager running smart pricing software and a property manager who built the software.

2. Operations run with the discipline your home deserves.

Our co-founder Stephanie Whitmore leads operations — and her standard is one of the strongest things about Cascadia Getaways. She brings two backgrounds most property managers don't have. Stephanie served in the military, where solid logistics aren't a slogan but a survival skill. Nothing falls through the cracks because the cost of a dropped detail is too high. And she grew up inside her mother's medical insurance coding business, where every claim has to be documented to forensic standard or it doesn't get paid.

That's how she runs operations here. Vendor relationships that get returned calls. Maintenance issues that get a paper trail. Insurance claims on guest damage that actually get filed correctly and actually get paid. A team that knows which homes have the tricky thermostat because most of them have been doing this for years.

Her team is fully in-house and Oregon-based. When your guest texts at 11 p.m. about the hot tub, they reach us — not a chatbot, not a contractor.

"Stephanie is the best property manager I have ever had. She is so nice and she always has an answer when I have questions. She provides good advice and it seems like we are always 'on the same page." — Dee, Lincoln City Homeowner

3. The owner relationship lives with a senior partner — not a portal.

Gerard Lester co-founded Cascadia Getaways behind 20+ years of experience in homeowner partnerships, hospitality, and business development. He shapes the relationship with the homeowners we serve, ensuring questions and concerns are addressed promptly and decisively — whether it’s strategy, market insight, or “should I add a hot tub?”

Most management companies push owner relationships several layers down the org chart. We’ve taken a different approach by placing it at the leadership level, because for homeowners, the relationship is the product.

"Thank you for going the extra mile, Gerard. You always bring the win-win." –Jake, Oregon coast homeowner

4. We were early on AI. We're not done building.

While most property managers are still figuring out ChatGPT, we were in the founding cohort of the first AI booking platforms in vacation rentals — building the connectors that let AI agents discover and book properties on behalf of guests. Your home is positioned for the next decade of guest discovery, not the last one.

But here's the part that matters more: our AI strategy is human-first. We use AI internally so Stephanie's team can spend more time caring for your home — and so we can take care of the people who take care of your home. We're not replacing humans with AI. We're using AI to give our humans more fulfilling work and more time for what actually matters: hospitality.

We'll send back a real, data-backed projection — built from Oregon-specific comps, not a generic algorithm.

What We Handle for You

A Full-Service Solution for Your Short-Term Rental

You bought a vacation home. You shouldn't have to run one. Here's what we do — so you don't have to.

• Listing Optimization. High-converting listings across every major platform with stunning photography, keyword-rich descriptions, and AI-enhanced ad delivery. Your home shows up where guests are actually looking.

• Sophisticated Direct Bookings. Our top-converting site and retargeting strategy drive 40% direct bookings for our owners — so you keep more of every dollar and we keep the guest relationship.

• Revenue Management. Our smart pricing tools adjust nightly rates based on demand, seasonality, and local events. But the algorithm is just the floor — Ryan's decade of Oregon-specific revenue experience is the ceiling.

• Guest Screening & Communication. From pre-arrival to post-stay, we handle everything. In-house. 24/7. Guests rave about our fast, friendly support and the proactive calls our team makes before and after every stay.

• Maintenance & Housekeeping. Professional teams clean and inspect after every stay. We manage every vendor relationship for repairs and upkeep — we truly care for your home.

• Owner Portal. Log in anytime to view bookings, statements, and performance metrics. Transparent owner reporting, trust accounting, and on-time monthly payouts.

• Compliance & Finances. We handle transient occupancy taxes, permitting support, and trust accounting so every penny is accounted for. Oregon STR regulations explained here.

Schedule a quick conversation with the actual people running Cascadia Getaways. No sales rep, no script, no pressure.

Trusted by Oregon Homeowners

What Our Owners Are Saying

“Cascadia Getaways has been an outstanding partner in managing our vacation rental. They’re professional, responsive, and consistently go above and beyond to ensure the property is well cared for and guests have a great experience. From handling bookings to maintaining the home, their attention to detail and communication have made the process smooth and worry-free. We’ve seen great results and feel confident knowing our property is in good hands. Highly recommend!”

— Aaron, Seaside Homeowner

“The Cascadia Getaways team is incredibly responsive and goes above and beyond with cleanliness and maintenance. They’ve helped us remedy everything from roof leaks to trees falling on our property. I could not recommend them more as a great partner / manager for vacation rental properties.”
— Jesse, Gearhart Homeowner

“Cascadia Getaways has been a fabulous partner for us with our Black Butte home. They have spent time to get to know us and our place, and have worked hard to ensure that guests have the highest quality experience when staying in our home. They are fabulous!”
— Mark, Central Oregon Homeowner

“I greatly appreciate the quick and complete responses to questions big and small. We’re a team. And Cascadia is a terrific teammate.”

— Rob, Seaside Homeowner

“Stephanie is the Best Property Manager I have ever had. She is so nice and she always has an answer when I have questions. She provides good advice and it seems like we are always “on the same page.” Gerard and Ryan are also fantastic. This team is very responsive and is always available to assist me when I request help. Gerard is very understanding. My situation has been dynamic and a bit unpredictable but Gerard has been very patient and flexible. I appreciate how he provides options and allows me to make the best decisions for myself and my family. Thanks so much, Cascadia Getaways!”

— Dee, Lincoln City Homeowner

Common Questions from Future Owners

Property Management FAQs

Q: How much do your services cost?
A: We offer competitive management fees with no hidden charges. Rates vary based on property type and services needed—contact us for more! We also offer a maintenance program to help keep costs predictable.

Q: Do you work with homes outside Oregon?
A: No. Our strength is in our hyper-local focus. We serve homes exclusively in Oregon.

Q: What platforms do you list on?
A: Airbnb, Vrbo, Booking.com, Google Travel, Expedia, HomeToGo, Saavy, Trip.com, Whimstay, Hopper, Directo, AirDeal and our own high-converting website. We are constantly evaluating our distribution partners to ensure they align with our strategies for your home.

Q: Can I still use my home?
A: Absolutely. You set blackout dates for personal stays, and we manage the rest.

Q: What do you mean by Revenue Management? How do you do that?

Revenue management is the art and science of maximizing your property’s income by setting the right price, at the right time, for the right guest. Most people think it’s just about turning on Airbnb’s Smart Pricing or using a tool like PriceLabs — but that’s only a piece of it. Learn more about our revenue management here!

Have questions that are not here? Schedule a no pressure chat about your home and our industry!

Q: I self manage on Airbnb, why not just hire a co-host? What are the risks of relying only on Airbnb or Vrbo?
A: OTA policies can change overnight — forcing refunds, shifting fees to owners, or delaying payouts. All the while, you don’t own the guest relationship. With direct bookings, Cascadia Getaways protects owners from revenue loss. See how here!

Q: How are your incentives different from a national property manager?

A: We're Oregon-only and employee-owned. We don't have outside investors demanding 30% returns on their capital or a national footprint to subsidize. That means we don't have to extract value from your home or our team to hit a fund-level number. We grow when our owners and homes do well — full stop.

Q: Who actually runs my home?

A: All three of our co-founders are deep in the work. Ryan handles revenue strategy and pricing. Stephanie leads operations and the on-the-ground team. Gerard owns homeowner relationships and company growth. When you call us, you reach the person who can actually solve the problem — whether you connect with one of us or a member of our trusted team.

Ready to Learn More?

Let’s Talk About Your Home

We build great partnerships with homeowners who value quality, transparency, and guest experience. Ready to see what your home could earn with Cascadia Getaways?

Real numbers for your home. Response within 48 hours.

30 minutes. The actual people running Cascadia. No pressure.

Prefer email? Reach us at [email protected] Want to speak to someone local? Call us at (971) 350-2880