Family-friendly vacation rentals in Lexington

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.

Kitchen · Indoor spaces · Laundry

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

Family · Indoor spaces · Sleep quality

Charming Home in Southland – Cozy & Spacious!

Welcome to this charming 4-bed, 2-bath home in Lexington's Southland Drive area. Perfect for families, groups, or business travelers, it's within walking distance to local restaurants and cafes. Minutes away, explore downtown Lexington’s rich history, visit the iconic Keeneland Racecourse, or tour the University of Kentucky. Outdoor enthusiasts will love nearby parks and trails, while Bourbon fans can discover local distilleries. This home is your ideal gateway to Lexington’s finest attractions!

Kitchen · Indoor spaces · Bathroom

The Flower Pot

Welcome to The Flower Pot! Come and stay at our newly renovated mid century modern home complete with a record player collection and great natural sunlight. This location is a hidden gem in Lexington! HIGHLIGHTS: - One turn off main road for easy access to ALL attractions and necessities in Lexington - The Distillery District, Rupp Arena, Keeneland, Red Mile(Railbird Music Festival), UK Campus all approximately 10 MINUTES OR LESS - 1 King bed/ Two Queen Beds with smart TVs - New luxury bathroom

Kitchen · Family · Accuracy

Maryland Luxury Downtown Manor

Our Maryland Manor was designed to be a true Home away from Home.. with an indoor Slide for extra Fun!! Grab coffee, sit in the sleeping porch and slide back down for a refill! A creative, historic oasis perfect for exploring downtown Lexington! Located Downtown, Minutes walk to Rupp, Dining, Galleries, Night Life and Next Door to the Apiary. Paired with Off Street Parking and a large backyard, this stylish place to stay is perfect for group trips. We can’t wait to welcome you to our Home!

Family · Indoor spaces · Hospitality

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

Family · Kitchen · Sleep quality

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!

Kitchen · Family · Decor

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.

Indoor spaces · Family · Walkability

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

Indoor spaces · Family · Decor

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.

Indoor spaces · Family · Bathroom

The Rosewood Cottage of Lexington I Elegant & Cozy

Rosewood Cottage is one of Lexington's most unique and charming properties. Located steps away from Ashland Park and under 5 minutes to Downtown, this picturesque 1920's cottage offers history, charm and elegance in one extraordinary home. Relax with a bubble bath & champagne while reading a book from the host's curated collection, roast s'mores by the backyard firepit, or dive into some southern cooking in the newly renovated kitchen. This home away from home is not one to miss.

Family · Indoor spaces · Walkability

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Kitchen · Family · Long stay