Holiday rentals with a pool in Oldham County

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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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Top guest favourite

Home in Louisville

5 out of 5 average rating, 22 reviews

Louisville Country Manor - Pool & Pickleball!

This property is owned and hosted by the primary occupant Gary Jenkens. Brandon assists with communication. Louisville license LIC-STL-23-00832 PRIVATE PICKLEBALL COURT!! Relax and have fun at the Kentucky Country Manor, where luxury meets convenience on 5 acres of serene countryside just 20 minutes from downtown Louisville! This expansive property offers not one, but two main living quarters, ensuring ample space and privacy for all guests. The main house (5 bedrooms, 4.5 bathrooms) features

Guest favourite

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 favourite

Apartment in New Albany

4.92 out of 5 average rating, 12 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 favourite

Flat in Louisville

4.99 out of 5 average rating, 99 reviews

Sleek Luxury Apt: King Bed, Coffee Bar & Pool!

Stay in splendor as you enjoy the endless amenities and stylish touches this apartment has to offer! Enjoy a peaceful night's sleep on a comfortable mattress, and start your day with a complementary cup of coffee. Get a workout in the gym, hang out at the rooftop or walk around downtown. Being in the heart of downtown, the opportunities and activities are endless! To end the night, relax with a glass of wine and watch a movie on Hulu or Disney plus! Don't wait! Book your stay with us today!

Top guest favourite

Home in Bagdad

5 out of 5 average rating, 27 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 favourite

Home in Prospect

5 out of 5 average rating, 102 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 favourite

Flat in Louisville

4.88 out of 5 average rating, 203 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

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

Home in New Albany

4.85 out of 5 average rating, 53 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.

Guest favourite

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 favourite

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 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.