Holiday rentals with a pool in Jeffersonville

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, 407 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.

FamilyLocationComfort

4.89 out of 5 average rating, 70 reviews

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.

Flat in Jeffersonville

Lux Riverfront Condo in Louisville/Jeffersonville

Riverfront! Luxury! Skyline Views!!! This newly Renovated Luxury Riverfront Condo 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!

FamilyValueSleep quality

4.94 out of 5 average rating, 35 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

LocationFamilyCondition

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, 114 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 just blocks from the area’s newest restaurant corridor. We are dog friendly, and boast a large side-yard and sidewalks throughout. Also enjoy the neighborhood’s paved walking trail with a lake view.

ValueLocationAmenities

4.88 out of 5 average rating, 96 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.

Flat 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.

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Flat in Central Business District

4.96 out of 5 average rating, 158 reviews

Downtown | Walk to Restaurants, Free Parking

Experience Louisville like a boutique hotel stay in the heart of downtown. This luxury apartment sleeps up to 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 golf simulator, gym, a seasonal dip in the heated pool and hot tub, or a cozy movie night. Elevated comfort, prime location book your stay with us today.

LocationFamilyView

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.

LocationFamilyParks

Flat in Central Business District

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.

4.92 out of 5 average rating, 350 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!

FamilyValueQuiet

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.

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.

LocationFamilyTV

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, 69 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.

FamilyLocationNearby

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!

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Apartment in Jeffersonville

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.

4.88 out of 5 average rating, 50 reviews

BEST View of Louisville

Sip on a glass of bourbon/wine while enjoying the scenic view of the Louisville skyline on the private outdoor balcony. This stylish 2 bedroom/2 bath condo offers accommodations for 6 with all the amenities of home. Minutes away from horse racing, bourbon distilleries, hiking/biking trails, and nightlife. Churchill Downs- 13mins Louisville Airport- 12mins KFC Yum Center- 5mins Big Four Bridge- 2mins

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Popular amenities for Jeffersonville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.67 out of 5 average rating, 3 reviews

DERBY! The Ville Getaway! Centrally Located

LocationHospitalityPool

4.25 out of 5 average rating, 12 reviews

Rock & Roll Riverhouse | Pool | Mins to Louisville

LocationFamilyCheck-in

4.97 out of 5 average rating, 130 reviews

Louisville Getaway. Memories made here!

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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.

4.67 out of 5 average rating, 105 reviews

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

FamilyLocationComfort

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

LocationFamilyLong stay

5.0 out of 5 average rating, 12 reviews

Perennial Paradise

LocationFamilyNearby

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.

5.0 out of 5 average rating, 5 reviews

Derby Winner 4 bedrooms/3 baths Pool/Hot Tub

BathroomHospitalityCleanliness

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.

4.62 out of 5 average rating, 29 reviews

Home near Downtown Louisville

ValueLocationQuiet

Other holiday rentals with a pool

4.94 out of 5 average rating, 35 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!

FamilyLocationCondition

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.

4.81 out of 5 average rating, 32 reviews

Cozy & fun Studio Near Churchill Downs/Fairgrounds

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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.

4.83 out of 5 average rating, 118 reviews

Spacious Riverfront Condo Minutes from Downtown!

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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

LocationAccessComfort

Flat in Jeffersonville

4.67 out of 5 average rating, 6 reviews

Downtown Park Front Retreat | Walk Everywhere

ValueLocationPool

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

Flat in East Market District

4.63 out of 5 average rating, 8 reviews

Modern Nulu 2BR CozySuites 08

LocationValueSleep quality

A bright blue front door adorned with a cheerful 'hello' sign welcomes guests. Flanking the door are two large, round planters filled with green plants and colorful flowers. The natural stone wall adds texture to the entryway.