Holiday rentals with a pool in Jeffersonville

Guest suite in Jeffersonville

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.

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.

A modern living area features a light gray sofa adorned with decorative pillows and a plaid throw blanket. Two red armchairs complement the space, which is anchored by a dark coffee table. A colorful piece of wall art and large windows allow natural light to fill the room.

4.99 out of 5 average rating, 138 reviews

Downtown Apt – King Bed, Hot Tub, Pool & Parking!

Stay in splendor as you enjoy the endless amenities and stylish touches this apartment has to offer! Enjoy a peaceful night's sleep on a comfortable mattress, and start your day with a complementary cup of coffee. Get a workout in the gym, hang out at the rooftop or walk around downtown. Being in the heart of downtown, the opportunities and activities are endless! To end the night, relax with a glass of wine and watch a movie on Hulu or Disney plus! Don't wait! Book your stay with us today!

5 out of 5 average rating, 119 reviews

A well-arranged bed features a neutral-toned knitted throw and decorative pillows with unique shapes. A wicker tray in the center holds a bottle of champagne and four glasses, accompanied by two plates and napkins, creating an inviting setting.

Home in Prospect

Peppermint Cottage Norton Commons Walk, Eat & Shop

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!

4.88 out of 5 average rating, 58 reviews

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

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!

4.97 out of 5 average rating, 260 reviews

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 Schnitzelburg

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.

Apartment in Jeffersonville

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.

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

5 out of 5 average rating, 41 reviews

A spacious outdoor area is equipped with a large dining table surrounded by woven chairs, offering a comfortable setting for meals. The deck provides a view of the neighborhood, with cars parked below and homes in the background. Natural light creates an inviting space for relaxation.

Home in Prospect

Norton, PetFriendly, Bourbon, WiFi, Downtown, Shop

Step into your fall retreat in the heart of Norton Commons! Watch Hill Manor is your gateway to exploring downtown Louisville, Bourbon Trail, and rolling horse country. Enjoy crisp autumn days with a stroll to downtown local shops, great local dining, and community events right outside your door. The location also provides easy access to bourbon distilleries, scenic horse farms, golf courses, and seasonal activities like festivals and foliage tours. Book your Kentucky getaway today!

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, 387 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.

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.

4.91 out of 5 average rating, 266 reviews

4th Street Suites - Ali 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, 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.

5 out of 5 average rating, 47 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.

Flat 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.

Guest house in Louisville

A vibrant mural of horse racing creates a dynamic focal point on the wall of the cozy sleeping area. A spacious bed with blue bedding sits opposite a wall-mounted television, complemented by a small table on one side, enhancing the room's charm.

4.75 out of 5 average rating, 24 reviews

Cozy & fun Studio Near Churchill Downs/Fairgrounds

✨ Kick back in our bright and comfy studio on a peaceful 3-acre property! Just minutes from Churchill Downs, the Fairgrounds (perfect for concerts!), Iroquois Park, and downtown Louisville. Enjoy beautiful views, pool access, and even free training at our fitness gym. Ideal for event-goers, concert lovers, or anyone looking for a laid-back, unique stay. ☕ Grab a coffee on the back patio in the morning — you might spot our friendly family of deer wandering by!

Popular amenities for Jeffersonville 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.

4.66 out of 5 average rating, 56 reviews

Louisville KY Home w/Hot Tub & Pool

4.9 out of 5 average rating, 10 reviews

An aerial view of a spacious lakefront home is displayed, featuring a well-maintained infinity pool surrounded by a landscaped yard. The structure includes multiple peaked roofs, expansive decks, and lush green trees providing natural shade.

Home in Floyds Knobs

Luxury Retreat in Floyds Knobs

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.

Home in Jeffersonville

5 out of 5 average rating, 4 reviews

4 bedrooms/3 baths

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.

4.96 out of 5 average rating, 23 reviews

The Getaway!

New place to stay

The Ville Getaway! Centrally Located

5 out of 5 average rating, 5 reviews

Home

Beautiful house in suburban neighborhood

4.95 out of 5 average rating, 20 reviews

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 Schnitzelburg

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

4.86 out of 5 average rating, 21 reviews

An aerial view of the outdoor space reveals an infinity edge pool surrounded by illuminated stonework. Comfortable lounge chairs and a fire pit are positioned on the spacious patio, framed by lush greenery and flower beds, creating an inviting environment for relaxation.

Home in Goshen

The Boathouse: A Peaceful Paradise

Other holiday rentals with a pool

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.

4.91 out of 5 average rating, 188 reviews

4th Street Suites - Beautiful King Bed Suite

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.

4.88 out of 5 average rating, 248 reviews

4th Street Suites - Luxury King Bed Suite

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.

4.91 out of 5 average rating, 130 reviews

4th Street Suites - Comfortable King Bed Suite

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.

Luxury, Modern 1-Bedroom High Rise Condo

A living area features a dark leather sofa and two tufted chairs positioned around a circular wooden coffee table. A large piece of wall art and patterned curtains add visual interest. Natural light enters through the window and door leading to a small balcony.

4.95 out of 5 average rating, 129 reviews

4th Street Suites - Stunning 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!

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.