Kim Kelley turned an Annapolis family home into a focused short-term rental business by knowing her guest, tightening her systems, and building demand outside the OTAs.
Kim Kelley did not set out to become a short-term rental operator.
She and her family bought a home in Annapolis because their daughter, Lizzie, was attending the United States Naval Academy and playing varsity lacrosse. Kim wanted to be there for the games, the milestones, and the moments that come with having a child at a service academy.
For four years, the house was a second home.
Then Lizzie graduated, was commissioned into the Navy, and moved on to flight officer training.
Kim had to decide what to do with the house.
Sell it? Keep it? Rent it?
Her daughter hoped to return to Annapolis someday, so Kim decided to keep the house and “throw it on Airbnb.”
That is how The Goat Getaway began.
The First Lesson: This Is Not as Easy as It Looks
Before Kim could even list the home, she had to get through Annapolis licensing and compliance.
The city required a short-term rental license, inspections, fire extinguishers, first aid kits, smoke alarms, carbon monoxide detectors, and other safety requirements. Luckily, the home already had a sprinkler system. Without it, Kim may have needed to add one.
She also moved the property into an LLC, worked with attorneys, and made sure the legal structure was handled correctly.
So while the phrase was “throw it on Airbnb,” the reality was much more involved.
Live Like a Guest Before They Do
Once Kim got her first booking, she realized the house needed a guest-ready reset.
She flew to Annapolis, stayed for about 10 days, and lived in the home like a guest. She and Lizzie slept in different bedrooms, used the kitchenette, cooked meals, tested the flow of the space, and looked for anything that felt too personal or inconvenient.
That process helped Kim see the home differently.
A mirror in the wrong place, a room that needed greenery, a space that felt too stark — these were small details, but they mattered.
Hosts know their properties too well. Guests do not have that context. They only experience what is in front of them.
The Second Guest Changed Everything
Kim’s first guest had a great stay.
The second guest exposed the gaps.
The main issue was ants, which are a real challenge in Annapolis. Even though Kim had regular pest control, several days between stays allowed the problem to show up before the next guest arrived.
The bigger lesson was not just about bugs.
It was that Kim was 1,400 miles away in Dallas and could not solve a guest issue in Annapolis at 5:00 PM on a Monday.
She needed a real local team.
Remote Hosting Requires Boots on the Ground
Kim called her contractor and asked if he knew someone who could be her person on the ground.
His wife, Wendy, called back and offered to help.
That became one of the biggest turning points in the business. Wendy already knew the house, had strong attention to detail, and understood what the property needed. Kim flew up, spent the day with her, walked through the home, and defined the role.
Wendy then helped Kim find a stronger cleaning team.
For a remote host, that local support changed everything.
Kim now had someone who could inspect the house, coordinate issues, support turnovers, and make sure the property was actually guest-ready.
Pricing Was the Biggest Learning Curve
When Kim first listed the property, her pricing strategy was essentially a guess.
Five bedrooms, roughly $100 per bedroom, so about $550 a night.
Then she joined the Thanks for Visiting pricing bootcamp and later Strategic Host. When she set up PriceLabs, the recommended base rate was much higher — closer to $950.
At first, that felt too high.
Kim assumed Naval Academy families might not pay that kind of rate. But she tested it, trusted the process, and adjusted the strategy.
She also changed her minimum stays: weekends moved from three-night minimums to two, and weekdays moved from two-night minimums to one.
Bookings started moving.
Now, every Monday morning, Kim reviews her numbers. She looks at pickup, occupancy, market trends, booking windows, and whether pricing adjustments need to be made.
She does not set it and forget it.
She manages it.
Parent-Child Listings Unlocked Midweek Demand
Kim’s full home is five bedrooms, which works well for larger groups and big Annapolis weekends.
But during the week, that was not always what guests needed.
With guidance from the Strategic Host team, Kim created smaller versions of The Goat Getaway. Guests can now book the basement suite, a two-bedroom version, a three-bedroom version, or the full house.
This opened up a new audience.
Naval Academy parents may come midweek to visit their midshipman, bring them dinner, or spend time nearby. But midshipmen cannot always leave campus during the week, and parents may only need a one-bedroom stay.
A five-bedroom house is not what they are searching for.
By right-sizing the listing, Kim made the property visible to more guests.
She also noticed that three-bedroom homes had much stronger occupancy in her market than five-bedroom homes, so creating a three-bedroom version helped her compete where the demand already was.
70% Direct Bookings Did Not Happen by Accident
One of Kim’s biggest wins is that 70% of her bookings are direct.
That strategy came from a painful experience.
A bad New Year’s Eve guest booked through Booking.com, hosted a disruptive party, overstayed, created neighborhood issues, and left the house in terrible condition. Kim took it personally at first, but eventually used it as a push to take more control over where her guests came from.
Her husband told her to treat it like a business and find her guests elsewhere.
So she focused on the Naval Academy community.
Kim reached out to women’s lacrosse team parents, then connected with the men’s lacrosse community. Because she had been a team mom and was already trusted in that world, the property started booking for home game weekends.
She did not wait for a perfect website. She started with what she had and told the right people about the house.
That is the direct booking lesson.
Sometimes the audience is already there. You just have to reach out.
Metrics Still Matter, Even With Direct Bookings
Even though Kim is building strong direct demand, she still watches her Airbnb analytics every week.
She tracks first-page impressions, click-through rate, titles, hero images, descriptions, and how guests are seeing the property in search.
If the numbers are not where they should be, she changes something.
That might mean updating the title around July 4th, reordering photos, adjusting copy, or testing a different callout.
Direct bookings are important, but OTAs still provide useful data.
Kim uses that data instead of guessing.
One Property Became a Bigger Vision
Kim’s revenue goal for the year is $128,000.
That is not just from hoping the calendar fills. It comes from pricing, operations, direct bookings, market awareness, and consistent weekly attention.
She is also already looking at her next property, potentially in College Station, Texas, where she went to Texas A&M.
A few years ago, she would not have imagined herself as a short-term rental operator and investor.
Now, The Goat Getaway has become a business she is energized by.
The Bigger Takeaway
Kim’s story is not about getting lucky with a great house.
It is about learning the business quickly, taking action, and refusing to stay passive.
She built a team. She learned pricing. She created smaller listing configurations. She tapped into a niche community. She tracked her metrics. She turned one bad guest into a better direct booking strategy.
That is what changed the business.
The property was already there.
Kim just started operating it like an asset.
Download a transcript of this episode
Resources:
- #STRShareSunday: @thegoatgetaway
- Apply for Strategic Host!
- Pricelabs: Revenue management for hosts and property managers.
#STRShareSunday
Today’s STR Share spotlight is on Strategic Host Kim Kelley and her beautifully designed Annapolis retreat, The Goat Getaway.
What we love most about this property is how intentionally it’s designed around the guest experience. Kim has created a stay that feels elevated, easy, and flexible — especially for families visiting the United States Naval Academy.
This particular setup is a “right-sized” version of the home for smaller groups, giving guests access to:
- 2 king bedrooms
- 2.5 bathrooms
- fully stocked kitchen + coffee setup
- fenced backyard with fire pit
- ping pong room
- garage + driveway parking (a huge bonus in Annapolis)
And if guests need additional space? Kim thoughtfully offers optional add-on bedrooms instead of forcing travelers to pay for space they don’t need. That’s smart hospitality.
We also love how deeply personal this home is. Kim originally purchased the property while her daughter was attending the Naval Academy so their family could stay connected to her world — cheering at games, spending weekends together, and making memories in Annapolis. Now she’s created that same experience for other USNA families visiting the area.
The location is another major win:
- walkable to Navy–Marine Corps Stadium
- minutes to Downtown Annapolis
- close to the USNA Yard
- tucked into a quiet neighborhood that still feels convenient to everything
This is such a strong example of thoughtful hosting paired with operational strategy and flexibility.
Explore the property here:
https://www.airbnb.com/rooms/1534083991357957971
Follow along: @thegoatgetaway
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