Vacation rentals with a pool in Jefferson County

Guest suite in Louisville

4.96 out of 5 average rating, 395 reviews

Cherokee Park Oasis with Pool and Hot Tub

1 bdrm basement apartment with private entrance, bedroom, bathroom, and common area located adjacent to Cherokee Park. 3/4 mile walk to shops, restaurants, and entertainment on Bardstown Rd. Heated saltwater swimming pool (seasonal) and cabana with wet bar. Hot tub. 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. Owner occupies the main floor upstairs.

4.99 out of 5 average rating, 84 reviews

An inviting outdoor space features a spacious in-ground pool surrounded by a decorative fence. Lush green trees provide shade, while the backdrop showcases a sunset sky with soft purple hues. Comfortable lounge chairs are positioned near the water, enhancing the area's relaxing ambiance.

Home in Mount Washington

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

4.86 out of 5 average rating, 88 reviews

A cozy living room features a red three-seater sofa, paired with a beige armchair. A wooden coffee table sits in the center, with various decorative items on it. Artwork adorns the walls, and natural light filters through the window, highlighting a warm atmosphere.

Apartment in Prospect

Exclusive Farmhouse w/ a Romantic Garden View!

Discover rustic charm at this serene Prospect, KY retreat, nestled on a historic estate garden by the Smithsonian. Surrounded by retired thoroughbreds and saddlebreds, this unique stay offers a peaceful farm setting just 25 minutes from downtown Louisville. Perfect for weddings, family vacations, or romantic escapes, the home features a fully equipped kitchen, outdoor space, free parking, and self check-in. Unplug, recharge, and enjoy Kentucky’s natural beauty in a truly memorable setting.

Apartment in Jeffersonville

An aerial view of a multi-story building showcasing well-maintained landscaping and a central pool area. The pool is surrounded by lounge chairs and neatly trimmed hedges, with lush green lawn areas nearby. This setting offers spacious outdoor leisure options.

4.89 out of 5 average rating, 62 reviews

LUX Riverfront Studio Louisville/Jeffersonville

Location! VIEW! ! DERBY! This Newly Renovated, Luxurious Waterfront Studio is the perfect home for your Family or Business trip. Ideal for The KENTUCKY DERBY, Thunder, and Bourbon & Beyond. Enjoy walking distance to restaurants, Big Four Station, the bridge to Downtown Louisville, bars, and nightlife. It’s also a short drive to Concert Venues, the KFC YUM Center, KY EXPO Center, Amusement Parks, Hiking Trails, and the Bourbon Trail. Make this your home for an Amazing Stay in Kentuckiana!

5 out of 5 average rating, 123 reviews

An outdoor seating area is displayed, featuring two white armchairs and a stone-top coffee table, arranged on a green and white striped rug. String lights illuminate the space, which is bordered by tall green shrubs and a wooden fence.

Home in Prospect

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

Guest suite in Jeffersonville

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.

4.94 out of 5 average rating, 189 reviews

Explore Jeffersonville & Louisville/Book for Derby

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 our photos & read the descriptions under them. You’ll love our home because we are close to downtown Louisville & Jeffersonville yet tucked away enough for a peaceful, relaxing stay. No early check-ins allowed.

4.92 out of 5 average rating, 240 reviews

A resort-style pool area is showcased, surrounded by a modern building with large windows. Lounge chairs are arranged along the deck, offering a space for relaxation. The pool features steps and a smooth surface, inviting guests to enjoy the water.

Apartment in Louisville

4th Street Suites - Beautiful King Bed Suite

Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

Superhost

An aerial view showcases a spacious, rectangular in-ground pool surrounded by a stone deck. Adjacent to the pool, an inflatable water slide is positioned, featuring vibrant colors of blue, orange, and yellow, inviting fun and enjoyment.

4.91 out of 5 average rating, 164 reviews

Sleeps 16, Heated Pool , Hot tub, Close to Dwtn

5000 square foot house set on a beautiful lot backed to a nature reserve park. Total of six bedrooms, three and half bathrooms. 5 large bedrooms with 5 queen beds each, 3 singles on the second floor and a mother-in-law suite with a king size bed and a single bed on the first floor. pool and hot tub. Pool is open from May 15 to October 15 and will be heated from Sep 15 to Oct. 15. Inflatable Water Slide is upon request. Gas grill on the deck and propane tank is available.

A cozy living area is furnished with a navy blue sectional sofa and two red chairs. Natural light enters through large windows adorned with teal curtains. A round wicker coffee table sits at the center, accompanied by a potted plant, while art is displayed on the walls.

4.97 out of 5 average rating, 268 reviews

8 Min to Bourbon Fest | 6 Kings + Hot Tub

• Spacious 5BR, 5BA home—great for groups • 1st floor: king bedroom + full bath in hallway • 2nd floor: two king en-suites + queen w/ hall bath • Walkout basement: two king beds w/ privacy curtains, full bath + living room • Hot tub • Fast Wi-Fi • Easy street parking • Minutes to Expo Center, Churchill Downs & Downtown • Derby, Bourbon & Beyond & Louder Than Life guests must inquire first, strict cancellation policy required. • Rental agreement + damage deposit required

4.96 out of 5 average rating, 152 reviews

A light-filled living area features a comfortable sofa adorned with soft throw pillows and a cozy blanket. A modern coffee table displays a decorative arrangement of flowers, while a colorful artwork of a tree enhances the inviting atmosphere. Large windows provide views of the surrounding buildings.

Apartment in Louisville

Stylish DT Apt • King Bed, Gym, Pool + Hot Tub

This stylish, luxury apartment is ideal for couples, families, and small groups. Step inside to modern finishes, updated appliances, and thoughtfully designed décor with everything you need for a comfortable stay. Rest easy on a plush bed, then head out to explore Louisville top attractions, dining, and entertainment are just steps away. Prefer to stay in? Enjoy on-site amenities including a gym, rooftop access, and a golf simulator. Book your stay today.

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.

4.97 out of 5 average rating, 58 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.

Superhost

A serene backyard features a sparkling pool surrounded by landscaped gardens, including various shrubs and decorative stones. The house, characterized by a brick facade and a sloped roof, provides a welcoming backdrop under a clear blue sky.