Family-friendly vacation rentals in Lexington

Updated 1910 charm! Walk to Rupp/near Keeneland!

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert/sporting event at nearby Rupp Arena (5 min walk), stroll through Gatton Park (2 min walk), view the horse races at Keeneland (10 min drive), tour the Alltech bourbon distillery around the block, or explore the offerings of downtown just outside your front door

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

Location! DWTN next to Rupp, KING BED w/ Parking

Welcome to 'The Shop'! This historic building once housed a general store right in the center of town! Now renovated with exposed brick, 12' ceilings, polished concrete floors & a flood of natural light. Park for free, walk to events, concerts and games. Designed with relaxation in mind, the home includes two Smart TVs, ample seating, a King Size Bed with Sealy mattress. The kitchen is fully outfitted with new stainless steel appliances and basic kitchen amenities. Enjoy your stay downtown!

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's Bluegrass region, The Dew Drop In, (newly constructed in 2018) is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY's Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

Cozy Kenwick Bungalow in the Heart of Lexington

Welcome to your home away from home in Kenwick, one of Lexington's favorite neighborhoods! This classic bungalow has 3 bedrooms (queen beds in 2 rooms and 2 twin beds in another room) plus a bright basement room with a sleeper sofa. Sit outside on the covered front porch or sit on the back deck and enjoy the fenced in yard. Kenwick is centrally located and is an easy drive to many popular destinations including downtown, UK, the bourbon trail, the Kentucky Horse Park, and Keeneland.

The LOFT at Bell Place - Downtown/Horse Park💙

Welcome to the Bell Court community, a close-knit neighborhood w/ lots of children & discerning families. Parties & other activities that do not meet the standards of the community will not be tolerated. This top floor loft (Apt #3) has ONE off street parking space & a private secured entrance. Beautifully appointed w/ a king size bed & queen sleeper sofa. * Rupp - 2 miles * Keeneland - 9 miles * Horse Park - 11 miles * STR Reg #15071157-3 - Max occupants 4 *

Modern LUX Downtown Bungalow 💙 Tempur-Pedic Beds

Welcome to your Kentucky Home Experience this beautifully restored and aesthetically pleasing bungalow positioned just one street over from the popular Jefferson to West Sixth Street. Uber to the following: Rupp Arena, Convention Center, many nearby bars, breweries, and your choice of upscale or laid back restaurants. * Rupp Arena - 2 miles * Keeneland Racetrack - 9 miles * Kentucky Horse Park - 11 miles * STR Reg #15062369-7 - Maximum occupants 4

★Escape & Relax ~ Breathtaking Creekside Getaway★

Located on the same property as Kentucky’s most wishlisted Airbnb, this cozy glamping escape offers its own unique way to unplug, relax, and reconnect under the stars. Enjoy solitude, romance or family time inspired by nature. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access ✔ Cooking Station ✔ Hot water Learn more about this glamping haven below!

Cozy 1-bedroom in Lexington

Historical home located in the heart of Lexington, Kentucky. Few minute walk to Woodland Park, Kroger, Starbucks, bars, and restaurants. Gas station right around the corner. A convenient 3 minute drive and you're in the middle of downtown Lexington. Rupp Arena (1 mi), Kroger Field (1.5 mi), Keeneland (7 mi), Kentucky Horse Park (10 mi), Buffalo Trace Distillery (26 mi). 1GB fiber optic wifi. (This home is a duplex.)