Vacation rentals with a pool in Oldham County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Oldham County

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

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Guest favorite

An inviting backyard area showcases a glistening pool surrounded by palm trees and vibrant lounge chairs. A gazebo can be seen in the background, with a round table and chairs set in the foreground, creating a perfect space for outdoor relaxation.

Guest suite in Jeffersonville

4.93 out of 5 average rating, 182 reviews

Come Explore Jeffersonville & Louisville

The hot tub is available year round. Perfect for relaxing and de-stressing during your stay. The pool is open May 1 ~ Oct 1. You can stay in and binge watch movies from our collection of DVD's or your Apple TV app favorites on the 110 inch screen in the theater room. Please browse through our photos & read the descriptions under them. You’ll love our home because we are close to downtown Louisville & Jeffersonville but tucked away enough for a peaceful, relaxing stay. No early check ins allowed.

Guest favorite

The exterior of a three-story brick condo is displayed, featuring a green front door and decorative stone accents. Two sets of windows are framed by elegant arches, flanked by shrubs and colorful flowers. A well-maintained lawn offers a neat, welcoming appearance.

Condo in New Albany

4.91 out of 5 average rating, 11 reviews

The Farmacy BnB

Located in historic downtown New Albany. These are the only condos located directly next to the Mighty Ohio River. Walking distance to restaurants, shops, and entertainment. Immediate access to Ohio River Greenway walking trails, boat ramp, ampitheatre, and skate park. Seven minutes from downtown Louisville, KY. Optional Private Chef Dinners by the owner Himself, who is a French Culinary Graduate out of NYC, who has helped opened multiple restaurants from Naples, FL to right here in New Albany.

Guest favorite

A contemporary wooden structure stands against a clear blue sky, featuring a spacious deck and large windows. A swimming pool is framed by a concrete patio, offering an inviting area for relaxation. Lush greenery surrounds the property, enhancing the serene outdoor setting.

Home in Louisville

4.96 out of 5 average rating, 52 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

Top guest favorite

A spacious deck offers a view of a clear blue pool surrounded by a well-maintained lawn and abundant greenery. The serene pond reflects fluffy white clouds and a blue sky, enhancing the tranquil outdoor setting.

Home in Bagdad

5 out of 5 average rating, 26 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!

Top guest favorite

Home in Prospect

5 out of 5 average rating, 100 reviews

Stay at Peppermint Cottage in Norton Commons!

Step into Peppermint Cottage and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville's excitement, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, and YMCA with pool. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and Friday food truck festivities. Your ideal Louisville adventure awaits at Peppermint Cottage!

Guest favorite

A resort-style pool area is surrounded by lounge chairs, featuring a separate hot tub nearby. The pool is framed by landscaped greenery and a contemporary building exterior, with multiple balconies visible in the background.

Apartment in Louisville

4.88 out of 5 average rating, 201 reviews

4th Street Suites - Luxury King Bed Suite

Embark! Your refuge boasts a regal King Bed, a kitchen of sheer beauty, and streaming delights. Yet, it's the spellbinding allure of the resort pool, hot tub tales, golf dreams, and the lofty 7th-floor haven that set this place ablaze. With free parking and the pulsating energy of 4th Street Live at your doorstep, don't miss out! Secure your slice of luxury—book now for an unforgettable escape! Pool/hot tub schedule subject to change at the discretion of the property management company.

Superhost

An aerial view reveals a rectangular pool surrounded by a spacious deck. Lounge chairs are arranged alongside, and an umbrella-covered table sits nearby. The area is bordered by greenery, providing a sense of privacy and connection to nature.

Home in Borden

4.87 out of 5 average rating, 38 reviews

Private Country Getaway 20min to Louisville w/Pool

Enjoy staying at this spacious modern home located in a private wooded country setting. Only 20 minutes from downtown Louisville this is a great spot if you are visiting for Derby, the Bourbon-Trail, concerts, sporting events, family reunions, work events, and so much more! Large open floor plan and a large fully finished basement with a full bar that opens up to the pool. There are 2 grills, large flat screen TV's, a hot tub, stocked kitchen, and plenty of space to relax and spread out.

Superhost

A backyard features a heated inground pool surrounded by a spacious patio. Poolside loungers offer relaxation, while a net stands ready for games. A cozy seating area is positioned near the house, and a wooden fence provides privacy.

Home in New Albany

4.85 out of 5 average rating, 52 reviews

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/

➤Your perfect stay awaits at our spacious pad that sleeps 14: 1 King, 8 Queens, and 3 baths ➤Dive into Relaxation: Unwind in the heated inground pool or slide into the 6 person hot tub. An outdoor shower offers a refreshing touch after a dip. ➤Endless Entertainment: Let the good times roll in the game room, equipped for hours of fun. Yard games and outdoor entertainment. Channel your inner master chef on the 8 burner Weber grill. ➤Conveniently located for easy access to distilleries.

Top guest favorite

A heated saltwater swimming pool is surrounded by a concrete patio and lush greenery. The area features a spacious cabana with seating, a chaise lounge, and colorful pool floats. Nearby, a small garden and manicured lawn enhance the outdoor setting.

Guest suite in Louisville

4.96 out of 5 average rating, 369 reviews

Cherokee Park Oasis with Private Entrance

1 bdrm basement apartment with private entrance, bedroom, bathroom, and common area located adjacent to Cherokee Park. Owner occupies the main floor upstairs. 3/4 mile walk to shops, restaurants, and entertainment on Bardstown Rd. Heated saltwater swimming pool and cabana with wet bar. Centrally located within 10 minutes from downtown, Churchill Downs, the Zoo, the airport, golf courses and Kentucky Kingdom. Situated in a quiet, park-like neighborhood with ample parking.

Guest favorite

A rooftop pool area features a spacious swimming pool with a shallow section and an adjacent hot tub. Surrounding the pool, multiple lounge chairs are arranged for relaxation. Lush greenery adds a natural element to the setting, enhancing the tranquility of the outdoor space.

Apartment in Louisville

4.93 out of 5 average rating, 113 reviews

Luxury Downtown Apt: Pool, Hot Tub & Golf Sim!

Live in splendor on your visit to the 'Ville as you stay in this spacious one-bedroom apartment in the heart of downtown and all of the fun that Louisville has to offer! Wake up to a complementary cup of delicious coffee before enjoying a workout in our state-of-the-art gym or hit the town right from your doorstep, with tons of great restaurants, bars, live music at 4th St. Live, and plenty of other activities all within walking distance! Book your stay with us today!

Guest favorite

A lively pub area is highlighted by colorful lights reflecting off the dark wood floor. Bar stools form a seating arrangement around the counter, complemented by a large screen displaying content. Windows allow natural light to filter in, contributing to the welcoming ambiance.

Home in Shelbyville

4.94 out of 5 average rating, 66 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 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

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.