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Holiday rentals with a pool in Jefferson County

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Top-rated rentals with a pool in Jefferson County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A gazebo encloses a hot tub, softly illuminated by string lights. The warm, inviting glow contrasts with the evening sky. Beyond the gazebo, the outdoor area is visible with a paved path and a landscaped garden, promoting a serene atmosphere.
Guest suite in Jeffersonville
4.94 out of 5 average rating, 186 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.

Top guest favourite
An inviting open kitchen showcases modern appliances and a spacious countertop, perfect for meal preparation. A cozy living room features a plush sofa, complemented by natural light from nearby windows and tasteful decor that enhances the comfort of the space.
Home in Prospect
5 out of 5 average rating, 119 reviews

Peppermint Cottage Norton Commons w Breakfast

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
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.
Flat in Jeffersonville
4.88 out of 5 average rating, 59 reviews

Lux Riverfront Studio Louisville/Jeffersonville

Location! VIEW! LUXURY! POOL! This newly renovated Luxurious Water-front studio is your perfect home 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!

Top guest favourite
Flat in Prospect
4.89 out of 5 average rating, 71 reviews

Cozy Cottage in Smithsonian's of American Gardens!

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.

Guest favourite
A spacious backyard is illuminated by string lights at dusk, featuring a hot tub and multiple seating areas around a fire pit. The well-maintained lawn and patio area create a welcoming outdoor space for relaxation and gatherings.
Home in Louisville
4.97 out of 5 average rating, 260 reviews

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

*Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required* Germantown is a unique blend of past and present. Restaurants and local attractions including Monnik Beer Company and historic Nords Bakery just blocks away from the home, there is something for everyone. Conveniently located within reach of several desirable destinations - The University of Louisville, Churchill Downs, downtown Louisville and the NuLu district nearby.

Guest favourite
A welcoming exterior of a home features a covered front porch with two chairs and potted plants. Decorative shrubs and trees provide greenery, while the gray siding and white trim present a classic appearance. The front door is framed by large windows, enhancing natural light.
Home in Louisville
4.95 out of 5 average rating, 21 reviews

Germantown Gem - 3BR/2BA Home with Stock Tank Pool

This 3BR/2BA fully renovated home is in the heart of Germantown and close to the Highlands, KY Expo Center, Churchill Downs, UL, and Downtown Louisville! Ask about monthly discounts! • 3 Queen Beds • 2 Full Baths • Office with Monitor/Printer • Smart TV in Living Room and Projector with Apple TV in Primary Suite • Stock Tank Pool and Fire Pit in Backyard • Walk/Bike Score 75 ('Very Walkable/Bike able') • Fully Equipped Kitchen • Washer/Dryer • Coffee Shops, Restaurants, and Bars Walkable

Guest favourite
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.
Apartment in Jeffersonville
4.85 out of 5 average rating, 110 reviews

Spacious Riverfront Condo Minutes from Downtown!

Condo 12 minutes from Churchhill Downs, Perfect for Derby! 2-story townhome at The Harbours Condominiums directly across from Louisville overlooking downtown & the Ohio River! Indoor & outdoor pools & gym. Short walk to dozens of restaurants or take an easy stroll across the nearby walking bridge to downtown Louisville. 8.1 mi. to SDF Airport 6.7 mi. to Kentucky Expo Center 1.6 mi. to YUM Center 5.9 mi. Kentucky Fairgrounds/KY Kingdom 2.3 mi. to Louisville Bats Stadium 10 mi. to Zoo

Guest favourite
A modern living area features a gray sofa adorned with navy blue and white cushions. A light coffee table sits on a patterned rug, complementing the space. Behind, a dining area with a table and chairs is visible, along with a well-equipped kitchen showcasing stainless steel appliances.
Flat in Louisville
4.94 out of 5 average rating, 145 reviews

Chic Apt – Pool, Hot Tub, Gym & Golf Simulator!

Live in luxury while being in the heart of it all! This centrally located space has all of the amenities and ambiance for a lavish getaway! Enjoy a peaceful nights sleep on a king bed, and wake up to a complementary cup of coffee! Get a workout in at our state-of-the-art gym, or explore everything Louisville has to offer right from your doorstep! With tons of bars, restaurants, live music, and other activities within a block, you'll never be bored! Book your stay with us today!

Top guest favourite
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.
Guest suite in Louisville
4.96 out of 5 average rating, 388 reviews

Cherokee Park Oasis with Private Entrance

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 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. Owner occupies the main floor upstairs.

Guest favourite
A resort-style pool area is surrounded by lounge chairs, featuring a separate hot tub nearby. The pool is framed by landscaped greenery and a contemporary building exterior, with multiple balconies visible in the background.
Flat in Louisville
4.88 out of 5 average rating, 251 reviews

4th Street Suites - Luxury 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.
Home in Louisville
4.91 out of 5 average rating, 161 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.

Top guest favourite
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.
Flat in Prospect
5 out of 5 average rating, 47 reviews

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.

Popular amenities for Jefferson County rentals with a pool

KitchenWifiPoolFree parking on premisesAir 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.
Home in Louisville
4.67 out of 5 average rating, 57 reviews

Louisville KY Home w/Hot Tub & Pool

Top guest favourite
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.
Home in Louisville
4.96 out of 5 average rating, 24 reviews

The Getaway!

Superhost
Home in Louisville
New place to stay

The Ville Getaway! Centrally Located

Guest favourite
A modern kitchen area displays a wooden counter with storage drawers beneath. Above, a reclaimed wood shelf houses an assortment of books and decorative items. Two mini-fridges are positioned under the counter, enhancing functionality. A potted plant adds a touch of greenery to the space.
Home in Louisville
5 out of 5 average rating, 56 reviews

Countryside Getaway

Top guest favourite
A private outdoor area includes a heated pool surrounded by a concrete deck. Multiple lounge chairs are positioned around the pool, and an umbrella provides shade. Lush greenery and a wooden fence create a secluded atmosphere, enhancing the outdoor experience.
Home in Louisville
5 out of 5 average rating, 33 reviews

Entire House in The Highlands. Private Pool.

Top guest favourite
A serene backyard features a chemical-free pool bordered by lush greenery and walking paths. Two lounge chairs provide seating areas for relaxation. The home’s exterior is visible in the background, complemented by a cloudy blue sky and clear sunlight.
Home in Jeffersonville
5 out of 5 average rating, 7 reviews

Urban Lakeside 3BR Retreat w/ Private Pool

Superhost
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
4.75 out of 5 average rating, 88 reviews

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

Top guest favourite
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
5 out of 5 average rating, 43 reviews

NEW Golf, Horse, Bourbon, Shops, Downtown, Pets

Other holiday rentals with a pool

Top guest favourite
A comfortable living room features a dark leather sofa with accent pillows, a coffee table positioned at its center, and a medium-sized television mounted on the wall. Natural light filters in through large windows covered by patterned curtains, while a door leads to a small balcony.
Flat in Louisville
4.91 out of 5 average rating, 134 reviews

4th Street Suites - Comfortable King Bed Suite

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.
Flat in Prospect

Acadia II Apt. in the Commons

A spacious living area features a large television displaying a vibrant outdoor scene. A comfortable sofa is positioned in front of the TV, with a side table and lamp nearby providing soft illumination. Toys can be seen on the floor, adding a playful touch.
Flat in Louisville

1br Condo

A spacious living area features a gray sofa adorned with a soft throw pillow, positioned beside a sleek coffee table. A large mirror reflects the room's light, enhancing the open feel. The kitchen area is visible in the background, showcasing dark cabinetry and modern appliances.
Flat in Louisville

Luxury, Modern 1-Bedroom High Rise Condo

Guest favourite
A modern studio apartment features a cozy king bed with vibrant red and black bedding. A stylish sofa adorned with decorative pillows is positioned in front of the bed. A fully equipped kitchenette is visible in the background, along with warm overhead lighting that enhances the inviting atmosphere.
Flat in Louisville
4.91 out of 5 average rating, 270 reviews

4th Street Suites - Ali King Bed Suite

A charming pink house with multiple levels is featured, presenting a classic architectural design. A spacious porch, framed by white railings, invites gatherings. A sign labeled 'Pink Castle' is positioned nearby, and the vibrant exterior is complemented by lush green grass and a clear blue sky.
Home in Jeffersonville

Pink Castle Babe’cation of Indiana!

Superhost
A spacious living area is depicted, featuring a comfortable gray sofa with decorative pillows positioned next to a side table. A modern kitchen with sleek cabinetry and stainless steel appliances is visible in the background. Large windows allow for ample natural light, illuminating the wood-style flooring.
Flat in Louisville
4.9 out of 5 average rating, 274 reviews

4th Street Suites - Opulent King Bed Suite

A spacious finished basement is shown, featuring a light-colored bed with decorative pillows. A dining table with chairs is seen in the background, alongside a kitchenette. Ceiling lights provide ample illumination, enhancing the inviting atmosphere of the area.
Home in Louisville

Cozy Private Finished Basement

Destinations to explore