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!

Private Estate on Bourbon Trail : KY Derby : Pool

Welcome! Bring the whole family to Horse & Bourbon Country with plenty of room for fun. Enjoy a day at any of the local Distilleries with Bulleit, Wild Turkey, Buffalo Trace and many more within a 25 minute drive and then come back to a relaxing sunset on a spacious back deck with a view of the pool, hot tub and fully stocked 1 acre pond. You can enjoy a night of Billiards, Shuffleboard or a movie inside the Theatre room. Situated between Churchill and Keeneland there is something for everyone!

4BR Farm~Bourbon Trail~private 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. Pool May thru Oct. heated 85*. Horse boarding available.

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.

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.

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

Discover Kentucky's Finest - B on the Bourbon Trail. With a saltwater pool, hot tub, fire pit, and Pub B, this historic colonial estate on 3 acres is near over 30 renowned distilleries, 35 minutes from the iconic Churchill Downs, and just an hour away from the prestigious Keeneland racecourse, B On The Bourbon Trail offers unparalleled access to Kentucky's most treasured attractions and promises an unforgettable experience in the heart of Kentucky's bourbon country.

Bourbon trail luxury 4 bdrm getaway!

This stunning luxury home is perfect for any occasion! Located just 15 minutes from downtown Louisville/Churchill Downs. Large living room, games room will provide you with all the comforts and space for you and your friends/family needs. You can spend your time relaxing in the pool (summer only), sitting by a fire, catching a game on the outdoor deck, BBQing, sitting at the bar or playing games. Pool is open April 26 to September 5 for the 2024 season.

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.

4BR Hot Tub. Game Room. Near Lake

Relax and unwind at this spacious retreat in Shelbyville, Kentucky! Enjoy your own private oasis with a sparkling pool, soothing hot tub, and fun-filled game room — perfect for families or groups. Conveniently located near local attractions, wineries, and scenic countryside. The ideal getaway for comfort, fun, and relaxation! Pool is closed for the season. Professional photographs coming soon (the current photographs do not completely do justice)

Kentucky Bourbon & Bluegrass Retreat* March 26

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

Hot Tub, 10 min to Bulleit

Escape to our serene haven nestled in the heart of the Kentucky Bourbon Trail. This inviting property offers the perfect home base for your bourbon tasting adventures. The Bourbon Bungalow is located in a rural/residential area across the street from Guist Creek Lake in the charming town of Shelbyville. We are midway between Louisville and Lexington and perfectly situated for visits to a plethora of distilleries.

Cozy Cottage on Firefly Farm

Carriage House Garage with breathtaking views of Firefly Farm. Conveniently located in Bourbon Country just thirty minutes away from Louisville or Frankfort. Enjoy meet and greets with our donkey and her flock of sheep, beautiful sunrises and sunsets from the comfort of your own private porch, and so much more.