353 Owsley Ave

Relax and play in this spacious 4-bedroom + loft home in Lexington, perfect for groups of 12. Enjoy amenities like a golf simulator, game room, hot tub, fire pit, and a cozy covered porch. Centrally located near historic downtown and all things Bluegrass.

About This Space

Step through the front door and the whole group fits comfortably. The open-concept main floor centers on a gas fireplace and a sectional built for a crowd, flowing straight into a fully stocked kitchen with stainless appliances, granite counters, and an island with seating for three. The dining table seats eight, so nobody eats standing up. Sleeping is where this house earns its keep. The first-floor Master Suite has a king bed and an ensuite with a walk-in shower and soaking tub -- a quiet retreat away from the group. Upstairs, two more king rooms share a Jack-and-Jill bath, a third bedroom holds two queens with its own ensuite, and an open loft at the top of the stairs adds a king bed for flexible sleeping. Six beds, four bedrooms, one loft, sleeping 12 without anyone on an air mattress. Bathrooms are stocked, not just clean -- body wash, shampoo, and conditioner in all three full baths, plus a half bath downstairs for guests who never leave the party. Then there's the reason half our guests rebook: the garage game room, with a Foresight golf simulator loaded with real courses, a ping pong table, and enough open floor for kids to run laps while the adults play a round. Outside, the covered porch is where coffee happens every morning -- rocking chairs, quiet street, good light. The private hot tub runs 24 hours, and the fire pit turns into the real living room once the sun sets: string lights, s'mores, stories that run long. A washer and dryer keep laundry easy for longer stays, and every bedroom has fresh linens plus extra pillows and blankets.

Location & What's Nearby

This farmhouse sits centrally in Lexington -- close enough that "what should we do today" is never a problem. Downtown Lexington and the Distillery District are about a 12-minute drive, home to Town Branch Distillery and the walkable brick streets our guests keep mentioning in reviews. Keeneland Race Course, one of the most beautiful tracks in America, is roughly 15 minutes away. Horse country is why most people come to Lexington, and the Kentucky Horse Park is about 20 minutes out -- working farms and horseback rides in one stop. Bourbon lovers have real options too: Buffalo Trace and Woodford Reserve are each roughly 30-40 minutes away, easy day trips for a Bourbon Trail itinerary. Closer to home, guests walk to a neighborhood coffee shop and a couple of casual restaurants that show up again and again in our reviews. University of Kentucky's campus and Rupp Arena are about 15 minutes away for game days and graduation weekends. Thoroughbred Park and the Kentucky Theatre round out a downtown evening. Drive times above are estimates -- we recommend confirming exact routes before locking in your day-by-day plans.

Who This Home Is Best For

Multi-generational family reunions: with a first-floor king suite and its own ensuite, grandparents get privacy while everyone else spreads across the upstairs bedrooms and loft. Golf buddies and game-day groups: the simulator alone justifies the trip, and the fire pit and hot tub give everyone a way to unwind after eighteen holes on the screen. Bourbon Trail road-trippers: use this house as home base, spend your days at Buffalo Trace and Woodford Reserve, and come back to a hot tub instead of a hotel lobby. Wedding and graduation parties: we've hosted UK graduation weekends and wedding groups who needed a house big enough to get ready together and celebrate together after. Families with young kids: a crib, fireplace guards, and pack-and-play keep little ones safe, while the private yard gives them room to run.

** NOTE: Rental Property Agreement is required to be signed up after reservation has been confirmed. Failure to comply will result to the cancellation of reservation without refund.

Please note that we have placed an electronic lock on the front backdoor for easy quick access. You are welcome to arrive any time after your check-in window.

We're lucky to live in a city where driving is an easy option for getting around. The parking isn't usually too much of problem, and you can hail either Uber or Lyft right from your driveway!

After confirming your reservation, you’ll receive access to our Guest Portal, which must be completed before check-in. It includes your check-in instructions, house rules, and required guest information.

You will also be asked to review and sign our external rental agreement. During this process, you’ll have the option to purchase a nightly damage protection plan (damage waiver) for coverage against accidental damages during your stay.

🐾 Pet-Friendly Stay We’re happy to welcome pets in our property! We allow up to 2 pets, and there is a $100 pet fee per pet. Please inquire and let us know in advance if you’re bringing pets so we can add the fee to your reservation. This helps us prepare the space and ensure a comfortable stay for you and your furry friends.

Registration # 15077859