Holiday rentals with a pool in Louisville

Guest suite in Louisville

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.

4.96 out of 5 average rating, 398 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.

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4.95 out of 5 average rating, 219 reviews

Luxury Retreat with Hot Tub

Welcome to Four Seasons Cottage on the Bourbon Trail! This charming property is located in a peaceful vacation community, just a short walk from the seasonal pool. Featuring 2 bedrooms, a fully equipped kitchen, and cozy living room with a fireplace, this cottage is perfect for a family getaway or a couples retreat. Enjoy the large deck with a hot tub and BBQ, as well as access to nearby hiking trails and attractions. Cottage 37 sits on a ridge that overlooks the 3,050-acre Taylorsville Lake.

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The cottage features a two-story structure with a light gray exterior and a welcoming entrance. A front staircase leads to a covered porch area, framed by well-maintained shrubs and greenery. Large windows provide natural light to the inviting living spaces within.

4.89 out of 5 average rating, 149 reviews

Lake Refuge near Louisville & Bourbon Trail #52

Cottage 52 is a bright and comfy 3 bedroom/3 bath cottage, fully equipped and furnished with extras and a hot tub on the rear deck. This cottage offers a new hot tub, HD tv, and DirecTV with 200 HD channels. Cottage 52 sleeps up to 8 people and stocked with everything you will need to recharge. Escape the commotion and routine of the city, and immerse yourself in a new environment, surrounded by nature and wildlife. This lakeside cottage will have you forgetting about your worries in no time .

ValueFamilyTV

5 out of 5 average rating, 127 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 !

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A two-story cottage is situated against a lush green backdrop. The exterior features light-colored siding, a covered porch, and multiple windows that allow natural light. A well-maintained lawn surrounds the home, enhancing the inviting appearance of the property.

4.94 out of 5 average rating, 186 reviews

The Gathering Place

The Gathering Place is the perfect place to get away and gather with family and friends. The resort is located conveniently between Bardstown, Louisville, and Frankfort on the Bourbon Trail. Offseason hiking, fireplace, and hot tub make a great peaceful getaway or work from "home" experience. Enjoy fishing, boating, kayaking, hiking, bird/deer watching and relaxing. The owners have been Resort guests for years and now own a cottage to enjoy and share with family, friends, and guests.

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Guest suite in Jeffersonville

4.94 out of 5 average rating, 190 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 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.

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Apartment in Central Business District

A modern bedroom features a cozy king bed with soft linens, a comfortable sofa, and a patterned area rug. Natural light filters through the large windows, with a green plant adding a touch of nature. Soft lamps provide additional lighting, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 330 reviews

4th Street Suites - Deluxe 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!

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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.

4.89 out of 5 average rating, 167 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.

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4.97 out of 5 average rating, 271 reviews

5BR w/ 6 King Beds + Hot Tub

• Spacious 5BR, 5BA home—great for groups • 1st floor: king bedroom + full bath in hallway • 2nd floor: two king en-suites + king 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

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Apartment in Central Business District

A cozy living area is featured with a large light-colored sofa adorned with various decorative cushions. Two lamps sit on either side of a wooden coffee table, which displays a decorative "hello" sign. Three wall art pieces showcasing plant designs are displayed above the sofa.

4.95 out of 5 average rating, 142 reviews

4th St Live | King · Pool · Hot Tub · Free Parking

Experience Louisville like a boutique hotel stay in the heart of downtown. This luxury apartment sleeps upto 4 with a king memory-foam bed and a queen memory-foam sleeper sofa for a restful night. Enjoy complimentary coffee and skyline views from your private balcony. Walk to dining, nightlife, and 4th Street Live!, then unwind with the heated pool, hot tub, golf simulator, gym, or a cozy movie night. Elevated comfort, prime location book your stay with us today.

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Guest suite in Shepherdsville

The outdoor space features a concrete patio surrounded by colorful trees, showcasing a blend of autumn hues. A charcoal and gas grill is covered, positioned on one side of the patio. The entrance door to the lower-level unit is visible, offering a private and secure access point.

4.99 out of 5 average rating, 101 reviews

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

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4.93 out of 5 average rating, 29 reviews

A charming brick building is shown with multiple balconies. The façade features large windows and doors, including red and green entryways. An outdoor seating area is visible, enhancing the welcoming appearance of this inviting rental.

Apartment in Prospect

Cozy City Condo in Norton Commons

Norton Commons – Your Perfect Getaway! This beautifully designed short-term rental combines modern comfort with timeless charm, offering an ideal stay for both leisure and business travelers. Whether you’re here for a weekend escape, a family visit, or a work trip, 9440 Norton Commons Blvd offers the perfect blend of style, comfort, and convenience. Book now and experience the best of Prospect, KY!

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Popular amenities for Louisville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 64 reviews

Louisville KY Home w/Hot Tub & Pool

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4.93 out of 5 average rating, 69 reviews

Home in Taylorsville

Bourbon Trail Lake Home w/ Hot tub & King Bed

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A split-level home is displayed, featuring a combination of brick and siding. A well-maintained garden with vibrant flowers lines the front. A mature tree provides shade, and the house is accented with dark shutters beside the windows. A welcoming sign is visible in the yard.

4.94 out of 5 average rating, 31 reviews

The Getaway!

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4.99 out of 5 average rating, 91 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

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4.93 out of 5 average rating, 55 reviews

A charming farmhouse is situated on a grassy lawn, surrounded by trees. An American flag is displayed in the front yard. The home features a welcoming front porch and a large attached garage, blending beautifully with the natural surroundings.

Home in Lebanon Junction

Happy Goose Hollow

ValueFamilyOutdoor spaces

5 out of 5 average rating, 6 reviews

Home in Jeffersonville

NEW Family Resort Home with Saltwater Pool & Games

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4.84 out of 5 average rating, 73 reviews

The exterior of a charming lakeside cottage is highlighted, featuring a staircase leading to a covered porch. The surrounding yard is landscaped with shrubs and trees, providing a natural ambiance. The cottage is set within a peaceful and green environment.

Home in Taylorsville

Whiskey River Lake Retreat

LocationFamilyPets

4.76 out of 5 average rating, 98 reviews

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.

Home in Jeffersonville

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

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Other holiday rentals with a pool

Farm stay in Simpsonville

The exterior of Sabre Hill Farm is captured, showcasing a multi-story, dark blue and wooden house surrounded by greenery. A gated entrance leads to a tree-lined driveway. A sign with the farm's name and address is prominently displayed in the foreground.

5 out of 5 average rating, 49 reviews

4BR Farm~Bourbon Trail~private heated pool~horses

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4.87 out of 5 average rating, 92 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!

LocationFamilyAir conditioning

Apartment in Jeffersonville

An aerial view captures the modern multi-story building with large windows, surrounded by well-maintained landscaping. A clear blue pool is visible at ground level, complemented by lounge chairs and greenery. The nearby outdoor lawn offers ample space for relaxation.

4.87 out of 5 average rating, 63 reviews

Lux Riverfront Condo in Louisville/Jeffersonville

ValueFamilyOutdoor spaces

4.92 out of 5 average rating, 52 reviews

The cabin features a rustic wooden exterior with a green metal roof, framed by surrounding trees. A welcoming front porch with railings and lights enhances the entrance. Two garage doors are visible on the lower level, creating an inviting atmosphere as dusk approaches.

Cabin in Shepherdsville

Pickleball*Hot Tub*Pool*Bourbon Trail*Sleeps 16!

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A living area features comfortable seating arranged around a wooden coffee table. A stone fireplace with an electric insert is positioned beneath a flat-screen television mounted on the wall. The warm red walls create a cozy backdrop, and kitchen facilities are visible in the background.

4.99 out of 5 average rating, 148 reviews

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

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5 out of 5 average rating, 61 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

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4.88 out of 5 average rating, 66 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

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A charming cottage exterior is framed by lush trees and rolling hills. A welcoming yellow door is complemented by a small front porch that features a chair and grill. The blue sky with fluffy clouds enhances the serene atmosphere, with a glimpse of the lake visible in the background.