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

Rental unit in Jeffersonville

4.89 out of 5 average rating, 18 reviews

Lux Riverfront Studio Louisville/Jeffersonville

Location! Access! Amazing View! This newly renovated Luxurious River-Front studio is your perfect Venue for your Family or business trip. great place for The Kentucky Derby, Thunder, Bourbon & Beyond. Walking distance to restaurants, Big four station, walking bridge to Louisville Downtown, great Bars,and Nightlife. It’s just a short drive to Concert Venues, KFC YUM Center, EXPO center, Amusement Parks, hiking trails and the Bourbon trail. Make this your home for an Amazing Stay in Kentuckiana!

Guest favorite

Home in Jeffersonville

4.95 out of 5 average rating, 57 reviews

Cozy Neighborhood Home - 10 min to Louisville!

Relax just 10 minutes from downtown Louisville at this beautiful patio home in a newly built community. Perfect for a weekend trip, business travelers, those with pets, travel nurses, and others! Quick, easy access to River City via I-65 or East End Bridge from a quiet, charming neighborhood. Equipped with an office space and fast fiber optic wifi for those working remotely. Grocery and restaurant options just 0.5 miles away. Also enjoy the neighborhood’s paved walking trail with a lake view.

Guest favorite

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 favorite

Farm stay in Simpsonville

5 out of 5 average rating, 21 reviews

Horse Farm 4Bedrm home Bourbon Trail ~private pool

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 8 horses, 14 goats and our Mule Judy. It is ideally positioned as home base for both indoor & outdoor activities including Derby & Horse Events, golfing and bourbon tours. Between activities unwind on the veranda or pool overlooking the horse paddocks. Animals are friendly and waiting for treats. Horse boarding options

Guest favorite

Home in Prospect

5 out of 5 average rating, 89 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

Home in Louisville

4.97 out of 5 average rating, 116 reviews

Louisville Getaway. Memories made here!

Unique Historic private home & guest house, perfect for the upcoming holidays! Main house is graciously appointed with plenty of room to spread out. Guest house has private entrance and it's own kitchen & laundry. Over 3800 sq ft in total! Fantastic covered outside porch area for eating & relaxing - very private. Comfortable beds with fine linens. Youtube TV & wifi. Photos don't do it justice! Located 6 miles from Downtown Louisville off River Road in an upscale area! Pool open seasonally.

Guest favorite

Home in La Grange

5 out of 5 average rating, 31 reviews

Luxury Retreat:Firepit, Hot tub, Man Cave, Karaoke

Escape to Glencairn Knoll, a luxurious 5,500 sq ft retreat on 3.75 acres, just 20 minutes from Louisville. Perfect for large groups, this elegant home features four bedrooms, 5 king beds, a private saltwater pool, firepit, hot tub, man cave, kids area, and multiple indoor and outdoor seating areas. Enjoy a fully equipped chef’s kitchen, cozy speakeasy lounge, and spacious living areas. Whether relaxing by the fire pit or exploring the nearby attractions, your unforgettable getaway awaits!

Guest favorite

Rental unit in Louisville

4.92 out of 5 average rating, 110 reviews

4th Street Suites - Splash 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.

Guest favorite

Townhouse in Louisville

5 out of 5 average rating, 22 reviews

Safe, scenic, convenient. Bordering a State Park!

Located in one of the safest parts of Louisville, this place is conveniently located by shops, restaurants, parks, and a movie theater, and only a few minutes from a major highway. Walk right out to the beautiful Tom Sawyer Park. Park features free to use nationally recognized BMX bike track, 6 tennis courts, 16 pickleball courts, a playground, an archery range, walking trails, shelters, and even an Olympic size pool with a splash ground (small entrance fee for pool and splash ground.)

Guest favorite

Guesthouse in Pendleton

4.88 out of 5 average rating, 59 reviews

The Waterfall Place, Suite and Walkout!

Get the double deal! The Waterfall Walkout (Sleeps 10+) + The Waterfall Studio Suite! (Sleeps 4+) PLEASE NOTE: This is a listing for the Walkout and Suite ONLY. It does not include the upper floor or the rest of the middle floor. Located only 35 minutes from downtown Louisville and Madison, Indiana. Relax in a country setting with serene nature! Perfect for LARGE groups, family vacations, or just a simple getaway! Welcome to Oldham County We look forward to hosting your stay!

Guest favorite

Guest suite in Louisville

4.96 out of 5 average rating, 368 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

Guest suite in Jeffersonville

4.93 out of 5 average rating, 180 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.