Holiday rentals with a pool in Shelby County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shelby County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Louisville

4.96 out of 5 average rating, 51 reviews

Bourbon Country Lodge • 5 Acre Resort Pool+Hot Tub

Escape to where the eagles fly with BNB Louisville's Bourbon Country Lodge! Over 5 beautiful acres of serene Kentucky countryside...a paradise perfect for friends and family to kick back and unwind. Relax poolside, soak in the hot tub or sip bourbon by the fire. No expense was spared in this top to bottom 4 br/4 bath renovation. Vaulted ceilings with massive picture windows flaunt incredible views of the landscape. Minutes from the Bourbon Trail, spectacular golf courses (Valhalla PGA 2024), sho

Guest favourite

Home in Frankfort

4.98 out of 5 average rating, 51 reviews

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 53 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!

Guest favourite

Home in Bagdad

5 out of 5 average rating, 24 reviews

Private Estate on Bourbon Trail w/ Beautiful 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!

Guest favourite

Farm stay in Shelbyville

5 out of 5 average rating, 36 reviews

Private & clean entire unit 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 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 Kentucky Horse Park & Churchill Downs. #VisitShelbyKY #bourbon #bourbontrail #Shelbyville #Louisville #Lexington #horses #farm #travelky #Kentucky #rental #vacation #travelnurse

Guest favourite

Farm stay in Simpsonville

5 out of 5 average rating, 22 reviews

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 3 horses, 14 goats and 2 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 includes May thru Oct. Ask me about boarding Horses.

Guest favourite

Home in Shelbyville

4.95 out of 5 average rating, 62 reviews

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.

Guest favourite

Home in Louisville

5 out of 5 average rating, 5 reviews

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.

Guest favourite

Home in Louisville

4.96 out of 5 average rating, 50 reviews

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.

Home in Louisville

5 out of 5 average rating, 3 reviews

Charm home with pool!

Our 4 bedroom home is situated in the middle of Polo Fields Community conveniently located 5 miles from the Gene Snyder Freeway, 20 miles from the Louisville International Airport and less than 5 miles to Valhalla Country Club! This custom built home is only 6 years old with an open concept first floor, large sunroom with TV, inground pool, and a finished basement with a bar, game room, kitchen/living area, bedroom and bathroom. No pets allowed.

Guest favourite

Home in Shelbyville

4.94 out of 5 average rating, 16 reviews

NEW - Hot Tub, Fully Loaded, 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.

Superhost

Home in Shelbyville

4.74 out of 5 average rating, 47 reviews

Pool*HOT TUB*Bourbon Trail

Are you looking for location? Look no further! This stunning home has everything your group could want! Centrally located with easy access to Louisville, Frankfort, Lexington, & so much more! In the summer the pool will be refreshing & all year long the hot tub will serve as a treat after a long day exploring! Let's not forget about the incredible game room with shuffleboard and pool table!

Superhost

Farm stay in Crestwood

5 out of 5 average rating, 15 reviews

Kentucky Horse Farm Stay- KY Derby/Yew Dell Garden

Enjoy a relaxing KY farm stay just minutes from Churchill Downs and less than a mile from the most popular Yew Dell Gardens, Waldeck Mansion or 3rd Turn Brewery! Whether you are in town for the races, bourbon or a wedding at Yew Dell - come relax at The Farm at Grace Hill. The original farm house from the 1870's, will sure to not disappoint you with its updated features and amenities.