Holiday rentals with a pool in Jeffersonville

A comfortable living area is furnished with a leather recliner and a wooden coffee table. A television is mounted on the wall opposite the open kitchen, where light cabinetry and seating at the counter are visible. Natural light enters the room, creating a warm ambiance.

4.95 out of 5 average rating, 113 reviews

Cozy Neighborhood Home - 10 min to Louisville!

Relax just 10 minutes from downtown Louisville at this beautiful patio home in a newly built community. Perfect for a weekend trip, business travelers, those with pets, travel nurses, and others! Quick, easy access to River City via I-65 or East End Bridge from a quiet, charming neighborhood. Equipped with an office space and fast fiber optic wifi for those working remotely. Grocery and restaurant options just 0.5 miles away. Also enjoy the neighborhood’s paved walking trail with a lake view.

ValueLocationWalkability

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, 404 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.

FamilyLocationBackyard

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.

4.91 out of 5 average rating, 77 reviews

LUX Riverfront Studio Louisville/Jeffersonville

Riverfront! Luxury! Skyline Views!! This newly renovated Luxury Riverfront studio is the perfect stay for your Family or Business trip. Now Ideal for walk downtown concerts, Thunder & Bourbon & Beyond. Walk to restaurants, Big Four Station, the bridge to Downtown Louisville, great bars, and nightlife. A short drive to major venues, the KFC YUM! Center, EXPO Center, amusement parks, hiking trails, and The Bourbon Trail. Make this your home for an Elevated stay in beautiful, vibrant Kentuckiana!

FamilyValueParking

4.94 out of 5 average rating, 33 reviews

Stable 6 | Fire Pits, Mini Golf, Games, Walkable

Barrel Proof Stays welcomes you to The Stables on Baxter – Stable #6, a 140-year-old converted horse stable in the heart of Louisville. Just ½ block from the Bardstown Rd/Baxter Ave corridor and minutes to NuLu, downtown, and Bourbon Trail distilleries. Enjoy beautiful design, shuffleboard, board games, and spacious living areas, plus a lively courtyard with mini golf, fire pits, grills, and outdoor seating. Walk to restaurants, bars, and shops. Additional Stables available for larger group

LocationFamilyCleanliness

4.87 out of 5 average rating, 94 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.

ValueLocationWalkability

5.0 out of 5 average rating, 130 reviews

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

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 !

FamilyLocationBackyard

Guest suite in Jeffersonville

4.94 out of 5 average rating, 191 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.

FamilyValueQuiet

Apartment in Central Business District

An expansive outdoor pool area is surrounded by lounge chairs, featuring a pristine swimming pool. Tall windows of the adjacent building reflect the sunny sky, while neatly trimmed greenery adds to the relaxing ambiance.

4.92 out of 5 average rating, 231 reviews

4th Street Suites - Extravagant 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!

LocationValueLaundry

4.97 out of 5 average rating, 275 reviews

6 Kings + Hot Tub | Near Expo, Track & Downtown

• 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

LocationFamilyBathroom

5.0 out of 5 average rating, 67 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.

FamilyValueIndoor spaces

Apartment in Central Business District

A rooftop pool area features a spacious swimming pool with a shallow section and an adjacent hot tub. Surrounding the pool, multiple lounge chairs are arranged for relaxation. Lush greenery adds a natural element to the setting, enhancing the tranquility of the outdoor space.

4.94 out of 5 average rating, 186 reviews

Downtown | Pool, Rooftop, gym & Free Parking

Enjoy an elevated stay in this spacious one-bedroom apartment in the heart of downtown, just steps from everything Louisville has to offer. Start your morning with complimentary coffee, then hit the state-of-the-art gym or head out to explore. Walk to top restaurants, bars, live music, and entertainment including 4th Street Live! all right outside your door. Comfort, convenience, and location come together for a stay that’s easy and memorable. Book today.

LocationValueAccess

4.58 out of 5 average rating, 48 reviews

Entire Home with Indoor Spa & Pool

Escape to Hot Tub Hideaway, a private 3-bedroom Louisville retreat just 10 minutes from downtown. This single-level home comfortably fits 6 guests and features a private indoor hot tub, a seasonal pool, and a fully equipped kitchen. Perfect for families or groups seeking a resort-style getaway with the comforts of home, complete with a fire pit, fast Wi-Fi, and a dedicated workspace. Your ideal base for exploring Louisville!

LocationFamilyHospitality

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.

4.72 out of 5 average rating, 68 reviews

Louisville KY Home w/Hot Tub & Pool

LocationValueCheck-in

4.98 out of 5 average rating, 53 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

Pet-Friendly Manor on Bourbon Trail, Pools, Golf

FamilyLocationHospitality

4.3 out of 5 average rating, 10 reviews

Rock & Roll Riverhouse | Pool | Mins to Louisville

LocationFamilyPool

DERBY! The Ville Getaway! Centrally Located

Pool

4.97 out of 5 average rating, 128 reviews

Louisville Getaway. Memories made here!

LocationValueBarbecue

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.

4.88 out of 5 average rating, 172 reviews

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

ValueLocationParking

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.

4.68 out of 5 average rating, 103 reviews

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

LocationValueHospitality

The exterior of a single-story brick house is displayed under a bright blue sky. Lush green grass surrounds the home, with contrasting shaped hedges and a nearby tree adding visual interest. The entrance is framed by a stone accent and adorned with two large windows.

5.0 out of 5 average rating, 7 reviews

Beautiful house in suburban neighborhood

LocationValueGetting around

Other holiday rentals with a pool

4.94 out of 5 average rating, 34 reviews

A cozy living room is featured, showcasing a large sectional couch and a flat-screen TV on a sleek stand. Built-in shelves with colorful items provide visual interest, while a fireplace offers warmth. Natural light illuminates the soft carpeted floor, enhancing the space's inviting feel.

Townhouse in Louisville

Safe, scenic, convenient. Bordering a State Park!

ValueFamilyBathroom

4.81 out of 5 average rating, 32 reviews

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.

Guesthouse in Louisville

Cozy & fun Studio Near Churchill Downs/Fairgrounds

ValueLocationAccess

4.83 out of 5 average rating, 118 reviews

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

Spacious Riverfront Condo Minutes from Downtown!

LocationFamilyLong stay

Guest suite in Louisville

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.

5.0 out of 5 average rating, 5 reviews

Charming Private In-Law Suite w/ separate entrance

LocationCleanlinessHospitality

A serene outdoor space is highlighted by a swimming pool surrounded by lush greenery. Two reclining chairs are positioned near the pool, complemented by flowering plants, creating a peaceful setting for relaxation.

Loft in Louisville

5.0 out of 5 average rating, 3 reviews

Charming Cottage & Pool near Churchill Downs

LocationCleanlinessHospitality

Apartment in Jeffersonville

4.67 out of 5 average rating, 6 reviews

Downtown Park Front Retreat | Walk Everywhere

ValueLocationAccess

The exterior of a single-story brick house is showcased, featuring a spacious driveway leading to a two-car garage. Lush green grass and a variety of trees surround the property, with a well-maintained landscape adding to the home's curb appeal.