INVESTOR-OPERATORS, NOT LANDLORDS
Craig and Matt built Stay Classy as investors first. We know what occupancy, ADR, and owner payouts feel like from the owner seat, and we manage with that lens.
SEE WHAT YOUR SAN DIEGO HOME COULD EARN
Enter your address and property details for an estimate based on local booking data and comparable homes. Get a clearer picture of your property's earning potential before deciding what comes next. Free, with no commitment.
"Stay Classy has been keeping my 2nd home property streamlined and most importantly occupied! Good communication and actual MANAGEMENT which is hard to find these days. Stay Classy stays on top of everything and keeps me informed. Highly recommend!"
Homes booked across the platforms guests already use
Matt Floyd & Craig GerulskiCo-Owners, Stay Classy Homes
About Stay Classy Homes
We are Matt Floyd and Craig Gerulski. In 2018 we stayed in our first Airbnbs in Nashville and Breckenridge and got hooked on traveling like locals. That experience pushed us into vacation rental investing while we were still in corporate W-2 jobs, chasing cash flow, appreciation, and a path to financial freedom we could actually share with family and friends.
What we kept seeing in short-term rentals was the gap between a beautiful home and how it was actually run. Slow guest replies. Flat pricing. Listings that did not match the property. Owners stuck coordinating cleaners and late-night requests instead of collecting the upside they bought the home for.
In 2019 we started Stay Classy Homes to manage our own properties first. Friends and colleagues asked for help, and we built a full-service team around design, photography, dynamic pricing, and day-to-day hospitality. We now manage properties in 5 states, keep a full-time operations team on the ground, and still treat every home like it is one of ours.
YOUR FREE PROJECTION
IN THREE SIMPLE STEPS
From your property details to a clearer picture of what your home could earn.
- 01
REQUEST YOUR PROJECTION
Enter your San Diego property address and a few details in the form above to request your free rental projection.
- 02
WE ANALYZE YOUR HOME
We use local booking data and comparable vacation rentals to prepare a personalized income estimate for your home.
- 03
RECEIVE YOUR RESULTS
Receive your personalized projection and explore your home's vacation rental potential.
100+
Properties under management
285
Five-star Google reviews
5
States with managed homes
2019
Year we started Stay Classy Homes
2 weeks
Typical path to a live listing when the home is ready
OWNERS FIRST.
STANDARDS ALWAYS.
We own vacation rentals ourselves, so we refuse to manage a home at a lower standard than we would accept on our own. Every property gets pricing attention, listing quality control, and a guest experience built to protect reviews and revenue.
DESIGN THAT BOOKS
Our interior designer looks for color and character that help a home jump off the screen. Then we shoot professional photos so the listing matches the stay guests actually get.
PRICING THAT MOVES WITH DEMAND
We use dynamic pricing (PriceLabs) and local market judgment so your rates track San Diego seasonality, events, and competitor supply instead of sitting on a flat nightly number.
HOSPITALITY THAT PROTECTS REVIEWS
Guest communication, cleaning quality checks, maintenance coordination, and 24/7 coverage are part of the job. Happy guests leave the reviews that keep your calendar full.
HOSPITALITY THAT GOES
BEYOND THE BOOKING
Guests should feel the difference the moment they open the door: a clean home, thoughtful touches, and a team that answers when something comes up.
That standard is how we operate across the portfolio. Design details, stocking, turnovers, and response times are managed on purpose, because those are the moments that show up in five-star reviews.
Strong guest experiences drive repeat stays and better search placement on the OTAs. When guests are happy, owners win. That is the only way we know how to operate.
CHOOSE HOW TO GET STARTED
SPEAK WITH US
Prefer to talk first? Call us at 619-738-6199 to discuss your property, your goals, and whether Stay Classy is the right management partner. Straightforward conversation. No hard sell.
Speak with usGET YOUR FREE INCOME ESTIMATE
Want the numbers first? Submit your address for a free rental projection built on local San Diego booking data. It is the fastest way to see what your home could earn as a vacation rental.
Get My Rental Projection