Vacation 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.

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Top guest favorite

A spacious, single-story house features a clean white exterior with dark roofing and large arched windows. Manicured grass surrounds a central pathway that leads to the front door, framed by evenly spaced shrubs. A clear blue sky adds to the welcoming atmosphere.

Home in Bagdad

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!

5.0 out of 5 average rating, 50 reviews

Top guest favorite

An aerial view of the rustic country home showcases a spacious outdoor area. A round above-ground pool is situated prominently among the green lawn, surrounded by wooden decking. Nearby, several tables and a picnic space are visible, inviting relaxation and gatherings in a tranquil setting.

Home in Frankfort

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!

4.97 out of 5 average rating, 110 reviews

Home in Bagdad

Farm Charm with all the amenities!

Bring the whole family to this find. Enjoy the pool, hot tub, pond, and game room—a great place for making memories with friends & family. Sleeps 16. 10 adults and 6 children. 5 rooms have queen-size beds, and 1 room has a double bunk, twin-over-twin and full-over-full. Two-car garage included. On the Bourbon Trail, minutes from Bulleit Distillery and Guist Creek Lake. Located halfway between Shelbyville and Frankfort; 50 min. to Louisville, 50 min. to Lexington. Three-night minimum.

New place to stay

A bright living area features a light-colored sectional sofa and two patterned armchairs. A coffee table is positioned in the center, and a mounted television is visible on the wall. Natural light floods through the windows, highlighting the modern decor.

Home in Shelbyville

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.

Superhost

A spacious saltwater pool is surrounded by a concrete patio and a protective wooden fence. Lounge chairs are arranged nearby under trees, providing shaded areas. A rustic structure and a shed are visible in the background, complementing the serene outdoor setting.

Home in Shelbyville

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!

4.93 out of 5 average rating, 86 reviews

Top guest favorite

The exterior of Sabre Hill Farm is captured, showcasing a multi-story, dark blue and wooden house surrounded by greenery. A gated entrance leads to a tree-lined driveway. A sign with the farm's name and address is prominently displayed in the foreground.

Farm stay in Simpsonville

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 with horses, goats and mules. It is ideally positioned 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 83. Treats for the goats and horses are provided.

5.0 out of 5 average rating, 57 reviews

Guest favorite

Home in Bagdad

*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, 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!

4.83 out of 5 average rating, 36 reviews

Top guest favorite

Home in Lawrenceburg

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.

5.0 out of 5 average rating, 20 reviews

Guest favorite

Home in Shelbyville

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.

4.92 out of 5 average rating, 75 reviews

Top guest favorite

A serene pool area is highlighted, surrounded by trees and open fields. The clear water reflects the sky, while a wooden picnic table sits nearby. An umbrella provides shade, and lounge chairs are positioned along the deck, offering a relaxed outdoor space.

Farm stay in Shelbyville

Clean guest house w/ donkeys on the bourbon trail

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. 5 min to Bulleit & 20-25 to Jeptha Creed & Buffalo Trace. Here for #horses? We're close to Lakeside Arena, Kentucky Horse Park & Churchill Downs. Sorry, no kids over 2 yo #VisitShelbyKY #bourbontrail #farm #travelky #Kentucky #rental #vacation #love #travel #insta

4.96 out of 5 average rating, 46 reviews

Top guest favorite

The outdoor area features a spacious swimming pool, surrounded by lush greenery and vibrant flowers. A covered porch is visible in the background, providing shaded seating options. The setting is brightened by natural sunlight, enhancing the tranquil atmosphere.

Home in Louisville

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.

4.97 out of 5 average rating, 62 reviews

Guest favorite

Home in Shelbyville

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

4.94 out of 5 average rating, 16 reviews