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, 403 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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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, 112 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.

FamilyValueHiking

4.91 out of 5 average rating, 76 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

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!

LocationValueGetting around

4.87 out of 5 average rating, 93 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.

ValueFamilyKitchen

Flat in Central Business District

A stylish bedroom features a spacious bed with crisp white linens, complemented by decorative pillows. The geometric accent wall incorporates shades of gold, gray, and white. Two bedside lamps provide soft lighting, while a potted plant adds a touch of greenery. Natural light streams through the window.

4.88 out of 5 average rating, 121 reviews

Urban Oasis: Pool, Golf Sim & Hot Tub Downtown

Enjoy everything Louisville has to offer from this luxury apartment, perfect for up to 4 guests. Rest easy on a comfortable king bed or memory-foam sleeper sofa, then wake up to complimentary coffee and sunrise city skyline views. Walk to top restaurants and entertainment , including 4th St. Live!. End your day with a virtual golf game, a workout in the 24/7 gym, a soak in the hot tub, or a relaxing movie night. Comfort, location, and amenities come together book your stay with us today!

FamilyValueOutdoor spaces

5 out of 5 average rating, 129 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 !

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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.

LocationValueHot tub

Flat in Central Business District

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, 322 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!

FamilyValueCleanliness

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

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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

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.

FamilyLocationHot tub

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!

ValueFamilyOutdoor spaces

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, 49 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

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 out of 5 average rating, 5 reviews

Derby Winner 4 bedrooms/3 baths Pool/Hot Tub

Sleep qualityBack gardenPool

DERBY! The Ville Getaway! Centrally Located

4.97 out of 5 average rating, 29 reviews

A well-maintained amphitheater sits beside a tranquil pond, surrounded by lush green grass. Stone steps lead up to the stage, which is supported by wooden beams. The sky transitions from deep blue to warm orange as the sun sets in the background.

Home in Prospect

Pet Friendly, Pool, Shops, Downtown, Bourbon, Golf

LocationFamilyAccess

5 out of 5 average rating, 8 reviews

Perennial Paradise

LocationFamilyPool

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 out of 5 average rating, 7 reviews

Beautiful house in suburban neighborhood

FamilyValueOutdoor spaces

4.3 out of 5 average rating, 10 reviews

Rock & Roll Riverhouse | Pool | Mins to Louisville

LocationFamilyPool

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.

4.72 out of 5 average rating, 102 reviews

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

FamilyLocationCheckout

4.83 out of 5 average rating, 6 reviews

The Bourbon Belle House

LocationParkingSleep quality

Other holiday rentals with a pool

Flat in East Market District

4.73 out of 5 average rating, 11 reviews

Bold Nulu 1BR CozySuites 03

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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 out of 5 average rating, 5 reviews

Charming Private In-Law Suite w/ separate entrance

LocationViewComfort

A cozy cottage exterior is seen, featuring a stone facade and a welcoming porch. The porch hosts rocking chairs, and the yard is surrounded by greenery. A sloped metal roof adds character, while trees provide a natural backdrop under a clear sky.

Home in Middletown

5 out of 5 average rating, 13 reviews

Charming & Cozy Cottage in Quiet Neighborhood

FamilyValuePool

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!

LocationFamilyCleanliness

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.

5 out of 5 average rating, 35 reviews

Entire House in The Highlands. Private Pool.

LocationFamilyKitchen

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, 117 reviews

Spacious Riverfront Condo Minutes from Downtown!

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