Holiday rentals with a pool in Shelby County

MacAttie Acres

Country home at MacAttie Acres in central Kentucky is conveniently located on the Bourbon Trail and in the middle of horse country. Located only 2 miles south of Exit 48 on I-64. Relax on the deck and enjoy the view of the farm, the horses grazing in the pasture or take a hike to the creek. 10 miles to Wild Turkey Distillery, 12 miles to Four Roses Distillery, 13 miles to Buffalo Trace, 29 miles to Keeneland, 48 miles to Churchill Downs, Stabling and turnout available for horses. Come visit!

Modern Farmhouse –Close to Horse Show & State Fair

Whether the Shelbyville or State Fair Horse Show this stunning Modern Farmhouse retreat is the perfect location. Nestled on 6 private acres surrounded by scenic horse farms, this spacious home is perfect for guests looking for comfort, convenience, and a touch of luxury during their stay. Parking for your horse trailer too. Experience a peaceful countryside escape, but just minutes from historic downtown Shelbyville, the Bluegrass Outlets, and 30 min to the State Fair or downtown Louisville.

*NEW* hot tub-sauna-large pool-game room-speakeasy

Escape to comfort and style at Expression on the Rocks: A newly renovated 6BR, 4400 sq ft retreat in the heart of the Bourbon Trail. Set on 5 lush acres with scenic views of hills and wildlife, this home offers a hot tub, sauna, inground pool (seasonal), firepit, speakeasy w/poker lounge, and gameroom. Perfect for group getaways-just minutes from Kentucky’s world-famous distilleries. Who needs to be the center of the universe when you can stay in the center of the Bourbon Trail? Book Now!

4BR Farm~Bourbon Trail~private heated pool~horses

Sabre Hill Farm house rental is the perfect place to immerse yourself in the relaxing sounds of nature. On the 25 acres you will find all the comforts of home on a farm with horses, goats and mules. It is ideally positioned as home base for both indoor & outdoor activities including Derby & Horse Events, group gatherings &/or bourbon tours. Between activities unwind on the veranda or pool overlooking the horse paddocks. Saltwater Pool May thru Oct. heated 85*. Horse boarding available.

B on the Bourbon Trail with Pub, Pool and Hot Tub

B on the Bourbon Trail: A Kentucky Original Gather your crew at this sprawling 1930s colonial estate on 3 acres. Offering authentic Southern charm, featuring a saltwater pool, hot tub, tiki bar, and Pub B—perfect for group fun! It’s your ultimate Kentucky home base: surrounded by 30+ legendary distilleries, close to championship golf like Valhalla and ULGC, near the iconic tracks of Keeneland and Churchill Downs, and 1 mile to historic Main Street. Spread out and soak up the Bluegrass!

Clean private unit with asses on the bourbon trail

Don't just visit Kentucky, experience it! Join us at Celebration Acres in #beautiful #Shelbyville. Centrally located between #Louisville & #Lexington, this private unit on our donkey farm is your refuge as you #explore #bourbon country. We're 5 min from Bulleit & under 20 miles to Jeptha Creed & Buffalo Trace. Here for #horses? We're close to Lakeside Arena, Kentucky Horse Park & Churchill Downs. #VisitShelbyKY #bourbontrail #farm #travelky #Kentucky #rental #vacation #love #travel #insta

A Little Piece of Heaven

Whether you are a couple on a getaway or a group looking for space for everyone, you will find this home to have plenty to do for everyone from the in-ground pool to the hot tub for 7 or just relaxing with open space with 2 large TV's on separate floors and a game room. It is centrally located to Louisville, Lexington, Frankfort, and Bardstown. If you are on the Bourbon Trail, it's within 1 hour of 90% of the States distilleries. Give us a try and I'm sure you'll be back.

Peaceful Bourbon trail home POOL hot tub 3 kings

This quiet Bourbon Trail home is designed for groups, with three king beds, one queen, and a twin daybed. The hot tub, pool table, and fully-stocked kitchen make group meals and relaxation easy. Open living and dining areas provide space to gather. Outside, a large dining area and separate seating area let you unwind. Grocery stores, restaurants, and distilleries are all nearby. The pool is open May - September, and the property is maintained for comfort and reliability.

Historic Briar Rose Estate | Sleeps 16 |

Briar Rose Estate: An Opulent Getaway in the Heart of Shelbyville, KY Welcome to Briar Rose Estate, where luxury, serenity, and timeless beauty converge. Nestled on 50 acres of Kentucky’s rolling green hills, our meticulously restored estate offers a peaceful escape from the ordinary. Whether you're seeking a relaxing retreat, a cozy family getaway, or a special place to celebrate life's moments, Briar Rose Estate provides the ideal backdrop for unforgettable memories.

Countryside Retreat

Welcome to your countryside retreat! This spacious and serene property is perfect for large groups. With 4 bedrooms, fully equipped kitchen and living spaces to accommodate the entire group this home is ready for your next getaway. Enjoy the views of 25 acres of rolling green Kentucky landscape from covered outdoor patios or take a dip in the private pool. With modern amenities and rustic touches, you will feel right at home in this serene landscape.

Bourbon Trail Retreat: Pool, Hot tub & Game Room

Welcome to The Shelby Stop where comfort & style awaits you! This 4 bedroom, 2.5 bath home offers space for everyone. 2 bedrooms are on the main floor; 1 of which is the luxury primary bedroom with en-suite bathroom. 1/2 bathroom just off the kitchen. The primary bedroom is a beautiful room with king size bed, luxury mattress, linens, large smart TV, sitting chair, & full size mirror. The attached en-suite bathroom is newly renovated in 2023

Bourbon Country Farm Stay | 6BR | Updated 2026

Recently Updated 2026! Bring the whole family to this spacious retreat on 5 acres with plenty of room to relax and have fun. Enjoy a pond, swimming pool, fire pit, pool table, ping pong, and multiple gathering spaces—too much to list! The pool opens on Memorial Day. A private, lighted pickleball or basketball court with nearby access. Less than 5 minutes from town and local winery and bourbon distillery. Newly remodeled, updated wifi.