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, 395 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.

Apartment in Jeffersonville

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.

4.87 out of 5 average rating, 61 reviews

Lux Riverfront Condo in Louisville/Jeffersonville

Location! Waterfront! Amazing Views! This newly renovated, Luxurious Riverfront condo is the perfect spot for your Family or Business trip. Ideal for the KENTUCKY DERBY, Thunder, and 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!

4.87 out of 5 average rating, 23 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

The Boathouse is located at the back of Tartan's Landing Marina off of the Ohio River. It sleeps up 7 people (1 king bed, 2 queen beds, 1 XL twin bed) has full kitchen and 2 full baths. Enjoy the infinity edge pool (open May-Oct), hot tub, outdoor fire pit, pickle ball area & private boat ramp (ARRANGEMENTS MUST BE MADE AHEAD OF TIME FOR A BOAT.) Heating the pool is optional for additional charge per day. All seasons are beautiful from the Boathouse located 30 min from downtown Louisville.

4.87 out of 5 average rating, 92 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.

5 out of 5 average rating, 125 reviews

An outdoor seating area is displayed, featuring two white armchairs and a stone-top coffee table, arranged on a green and white striped rug. String lights illuminate the space, which is bordered by tall green shrubs and a wooden fence.

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 !

Guest suite in Jeffersonville

4.94 out of 5 average rating, 189 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.

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.

4.92 out of 5 average rating, 250 reviews

4th Street Suites - Beautiful 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!

4.97 out of 5 average rating, 271 reviews

Home in Schnitzelburg

5BR w/ 6 King Beds + Hot Tub

• 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

A bright living space features a cozy beige sofa adorned with vibrant cushions. A round coffee table with decorative items sits in front. Natural light streams through large windows, illuminating the dining area with a simple table set for four, complemented by a colorful floral arrangement.

4.94 out of 5 average rating, 172 reviews

Downtown King Bed | Rooftop Views · Pool · 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.

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.

4.75 out of 5 average rating, 95 reviews

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

🚨3/4/25 Pool is open year round and can get as hot as a hot tub! This historical beauty has many stories to tell but even more memories for guests to make. Less than 8 minutes away from downtown Louisville. The 3 bedroom 2 bath layout works is ideal for a traveling families or mid-size groups. The heated pool and fire table in the backyard provides endless entertain. Please note the pool heat is a $60/day charge and requires a weeks notice to schedule

4.93 out of 5 average rating, 29 reviews

A charming brick building is shown with multiple balconies. The façade features large windows and doors, including red and green entryways. An outdoor seating area is visible, enhancing the welcoming appearance of this inviting rental.

Apartment in Prospect

Cozy City Condo in Norton Commons

Norton Commons – Your Perfect Getaway! This beautifully designed short-term rental combines modern comfort with timeless charm, offering an ideal stay for both leisure and business travelers. Whether you’re here for a weekend escape, a family visit, or a work trip, 9440 Norton Commons Blvd offers the perfect blend of style, comfort, and convenience. Book now and experience the best of Prospect, KY!

4.93 out of 5 average rating, 42 reviews

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.

Condo in Jeffersonville

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

Popular amenities for Jeffersonville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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.

4.7 out of 5 average rating, 63 reviews

Louisville KY Home w/Hot Tub & 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

Superhost

DERBY! The Ville Getaway! Centrally Located

The exterior of a two-story brick house is displayed, featuring white shutters and a welcoming entrance. A manicured lawn stretches in front, complemented by landscaped shrubs and trees. Blue skies with scattered clouds provide a bright backdrop to the home.

5 out of 5 average rating, 10 reviews

Home Baby Home

4.98 out of 5 average rating, 58 reviews

A colorful living area features a striking red ceiling and vibrant wall art depicting a circus theme. Seating includes a gray sofa, a round dining table, and unique patterned chairs. Large windows allow natural light to fill the space, enhancing the playful decor.

Home in Prospect

CIRCO LOCO - uNCommon Stay

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.

5 out of 5 average rating, 4 reviews

Welcome To KY!

A shaded patio area features a large wooden table surrounded by several black chairs. In the background, a heated saltwater pool is visible, framed by lush greenery and a serene atmosphere.

4.69 out of 5 average rating, 87 reviews

Spacious 5BR Getaway – Pool, Patios & Fun

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.

4.94 out of 5 average rating, 107 reviews

Cozy Neighborhood Home - 10 min to Louisville!

Other holiday rentals with a pool

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, 302 reviews

4th Street Suites - Luxury King Bed Suite

New place to stay

Backyard Paradise

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.

Apartment 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.

Apartment 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

Apartment in New Albany

Spacious 3 bedroom 2 full bath

A light-filled living area features a comfortable sofa adorned with soft throw pillows and a cozy blanket. A modern coffee table displays a decorative arrangement of flowers, while a colorful artwork of a tree enhances the inviting atmosphere. Large windows provide views of the surrounding buildings.

4.96 out of 5 average rating, 159 reviews

Relax & Recharge | King · Golf Sim · Pool · Lou