Holiday rentals with a pool in Louisville

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.

4.86 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.

Apartment in Central Business District

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.

4.92 out of 5 average rating, 240 reviews

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!

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.

4.97 out of 5 average rating, 268 reviews

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.

Home in Schnitzelburg

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

5 out of 5 average rating, 56 reviews

An open-concept living space showcases modern kitchen amenities, including stainless steel appliances and quartz countertops. A cozy seating area is arranged with a dark sofa and decorative rug, while sliding doors lead to a patio, enhancing the room's spacious feel.

Apartment in Prospect

The Lyric 185 - Norton Commons

Welcome the luxurious accommodations of the Lyric at Norton Commons. The Norton Commons neighborhood is an extremely walkable, mixed use development with shopping, restaurants, bars, and coffee shops. This unit is offered as a partnership with Watch Hill Proper, Louisville's premier bourbon destination. This unique partnership allows our guests the opportunity to participate in exclusive bourbon experiences, tastings, food pairings, and even private barrel selection.

Apartment in Central Business District

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.

4.96 out of 5 average rating, 152 reviews

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.

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.

4.7 out of 5 average rating, 63 reviews

Louisville KY Home w/Hot Tub & Pool

Come celebrate the holidays Kentucky style! Bring the whole family to our beautiful 4-bedroom - We can even host your family holidays! (One room in basement with no egress), 3-bathroom Louisville retreat with a Pool (open May-Oct), Jacuzzi Spa (Year round), Mini Gym with Dumbbells, and Recreation room with other amenities. The entire house is open for your experience. Kid and Family friendly, this guest favorite home is what you've been looking for.

Popular amenities for Louisville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

DERBY! The Ville Getaway! Centrally Located

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

4.4 out of 5 average rating, 5 reviews

A vibrant sunset casts hues of orange, pink, and purple across the lake, reflecting beautifully on the water's surface. The silhouette of trees and distant houses can be seen against the twilight sky, enhancing the tranquil atmosphere of the scene.

Home in Shepherdsville

Sunsets on Bourbon Street! Waterfront views!

Rock & Roll Riverhouse | Pool | Mins to Louisville

4.94 out of 5 average rating, 90 reviews

An outdoor space features a large swim spa hot tub beside a wooden bar with four stools. A gazebo is adorned with seating for relaxation. A stone pathway leads towards the backyard, with a manicured lawn and trees bordering the property.

Home in Clarksville

Close to everything / Huge

A backyard area features an inground pool surrounded by landscaped borders. A shaded seating area includes a sectional couch and two decorative planters with flowers. Decorative string lights are suspended above, enhancing the outdoor experience. A wooden fence and colorful autumn foliage provide a cozy backdrop.

4.74 out of 5 average rating, 94 reviews

Downtown->Heated Pool, Firepit, Bikes, Grill, Pets

New place to stay

Waterfront SweetEscape Pool HotTub Pets Views

5 out of 5 average rating, 48 reviews

A spacious living area features a large sectional sofa adorned with decorative pillows, a round coffee table, and a cozy armchair. A ceiling fan hangs above, and wooden wall decor adds character. The dining area is visible in the background, inviting communal gatherings.

Home in Prospect

No Guest Fees, NEW, Bourbon, Horses, Golf Nearby

Condo rentals with a pool

A view of the Ohio River is captured, featuring the downtown Louisville skyline in the background. A bridge spans the river, while a scenic waterfront area is visible with well-maintained greenery and a line of parked vehicles along the street.

Condo in Jeffersonville

4.82 out of 5 average rating, 113 reviews

Spacious Riverfront Condo Minutes from Downtown!

4.93 out of 5 average rating, 40 reviews

The panoramic view showcases the illuminated Louisville skyline at night, reflecting in the water below. Various colored lights from buildings create a vibrant display against the dark sky, while the bridge structure adds depth to the scene.

Condo in Jeffersonville

BEST View of Louisville

4.87 out of 5 average rating, 63 reviews

The living room features a light-colored sofa and armchair, complemented by wooden side tables. A large wall-mounted TV and a ceiling fan are visible, along with a plush area rug. Natural light comes from the door leading to an outdoor space.

Condo in Crestwood

Luxury Apartment/Near Louisville/EV Charger

Condo in Clifton

4.85 out of 5 average rating, 13 reviews

Modern Condo steps to Frankfort Ave

Other holiday rentals with a pool

A vibrant pool scene features illuminated water streams cascading into the tranquil water. A playful rubber duck wearing sunglasses is positioned centrally, adding a lighthearted touch to the evening atmosphere. Subtle lighting enhances the calming ambiance around the pool area.

5 out of 5 average rating, 4 reviews

Derby Winner 4 bedrooms/3 baths Pool/Hot Tub

A modern living area features neutral-toned furnishings, including a spacious sofa and two accent chairs. A coffee table sits centrally, complemented by a textured area rug. A large flat-screen television is mounted on the wall, and warm lighting highlights the open kitchen area in the background.

Apartment in Prospect

Acadia II Apt. in the Commons

Guesthouse in Shepherdsville

A view from the guest house porch reveals a serene pasture with several horses grazing. A black wooden fence encircles the expansive, green field under a clear blue sky, creating a peaceful rural atmosphere. The surrounding trees provide a natural backdrop.

4.94 out of 5 average rating, 54 reviews

Bourbon Country/ Derby Guest House

Home in Beechmont

4.73 out of 5 average rating, 11 reviews

6BR House Near Kentucky Exposition Center | w Pool

A comfortable living area features a gray sectional sofa adorned with colorful cushions and an orange decorative ball. A glass coffee table stands in the center, complemented by two lamps on either side, providing soft illumination. A vibrant abstract painting adds a touch of color to the wall.

Guest suite in Louisville

5 out of 5 average rating, 4 reviews

Charming Private In-Law Suite w/ separate entrance

5 out of 5 average rating, 13 reviews

A cozy cottage exterior is seen, featuring a stone facade and a welcoming porch. The porch hosts rocking chairs, and the yard is surrounded by greenery. A sloped metal roof adds character, while trees provide a natural backdrop under a clear sky.

Home in Middletown

Charming & Cozy Cottage in Quiet Neighborhood

A spacious backyard is highlighted by a well-maintained swimming pool, featuring a yellow slide. The patio area includes a covered seating space with a view of the house's large windows and deck above. Lush greenery frames the setting, complementing the tranquil atmosphere.

5 out of 5 average rating, 4 reviews

Southerland Vacation Home