Vacation rentals with a pool in Central Business District

Guest suite in Louisville

4.96 out of 5 average rating, 390 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.

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, 187 reviews

Explore Jeffersonville & Louisville/Book for Derby

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.

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.

4.89 out of 5 average rating, 62 reviews

LUX Riverfront Studio Louisville/Jeffersonville

Location! VIEW! ! KY DERBY! This newly renovated, luxurious Waterfront Studio is the perfect home for your Family or Business trip. Ideal for The Kentucky DERBY, Thunder, and Bourbon & Beyond. Enjoy walking distance to restaurants, Big Four Station, the bridge to Downtown Louisville, bars, and nightlife. It’s also a short drive to Concert Venues, the KFC YUM Center, KY EXPO Center, Amusement Parks, hiking trails, and the Bourbon Trail. Make this your home for an amazing Stay in Kentuckiana!

4.9 out of 5 average rating, 78 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.

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.

4.96 out of 5 average rating, 152 reviews

4th Street Suites - Stunning King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

5 out of 5 average rating, 123 reviews

A cozy living area is highlighted by a fireplace and large windows allowing natural light. A round coffee table is positioned at the center of a comfortable seating arrangement that includes a sectional sofa and armchairs. Potted plants add a touch of greenery.

Home in Prospect

Peppermint Cottage Norton Commons w Breakfast

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 !

4.8 out of 5 average rating, 76 reviews

An inviting inground pool features a gentle fountain and a volleyball net. Surrounding lounge chairs offer relaxation by the water, and a vibrant green lawn enhances the outdoor area. A boundary fence provides privacy, while a sunny sky completes the serene atmosphere.

Home in New Albany

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/

➤Your perfect stay awaits at our spacious pad that sleeps 14: 1 King, 8 Queens, and 3 baths ➤Dive into Relaxation: Unwind in the heated inground pool or slide into the 6 person hot tub. An outdoor shower offers a refreshing touch after a dip. ➤Endless Entertainment: Let the good times roll in the game room, equipped for hours of fun. Yard games and outdoor entertainment. Channel your inner master chef on the 8 burner Weber grill. ➤Conveniently located for easy access to distilleries.

4.91 out of 5 average rating, 162 reviews

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.

Home in Louisville

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.

4.97 out of 5 average rating, 262 reviews

A cozy living area is furnished with a navy blue sectional sofa and two red chairs. Natural light enters through large windows adorned with teal curtains. A round wicker coffee table sits at the center, accompanied by a potted plant, while art is displayed on the walls.

Home in Schnitzelburg

Hot Tub | 5BR/5BA | King Beds | Expo

• Spacious 5BR, 5BA home—great for groups • 1st floor: king bedroom + full bath in hallway • 2nd floor: two king en-suites + queen 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

5 out of 5 average rating, 51 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.

4.77 out of 5 average rating, 26 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

✨ 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!

A modern living area features a gray sofa adorned with navy blue and white cushions. A light coffee table sits on a patterned rug, complementing the space. Behind, a dining area with a table and chairs is visible, along with a well-equipped kitchen showcasing stainless steel appliances.

4.94 out of 5 average rating, 150 reviews

Downtown Apt • Pool, Gym, Hot Tub + Golf Simulator

Experience Louisville like a boutique hotel stay in the heart of downtown.This luxury apartment sleeps up to 2 with a king memory-foam bed for a restful night. Enjoy complimentary coffee and courtyard views from your apartment. Walk to dining, nightlife, and 4th Street Live!, then unwind with the heated pool, hot tub, golf simulator, gym, or a cozy movie night. Elevated comfort, prime location book your stay with us today.

Popular amenities for Central Business District rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Jeffersonville

4.5 out of 5 average rating, 4 reviews

Home in Jeffersonville IN

4.68 out of 5 average rating, 60 reviews

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.

Home in Louisville

Louisville KY Home w/Hot Tub & Pool

5 out of 5 average rating, 5 reviews

Home in Louisville

DERBY! The Ville Getaway! Centrally Located

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.

Home in Jeffersonville

Beautiful house in suburban neighborhood

5 out of 5 average rating, 43 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

Home in Cherokee Triangle

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, 33 reviews

Entire House in The Highlands. Private Pool.

East End Bungalow

Home in Jeffersonville

5 out of 5 average rating, 7 reviews

Urban Lakeside 3BR Retreat w/ Private Pool

Other vacation rentals with a pool

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.

4.92 out of 5 average rating, 155 reviews

4th Street Suites - Comfortable King Bed Suite

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, 219 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.

4.89 out of 5 average rating, 272 reviews

4th Street Suites - Luxury 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.

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

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, 293 reviews

4th Street Suites - Ali King Bed Suite

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.