Holiday rentals with a pool in Central Business District

Guest suite in Louisville

4.96 out of 5 average rating, 388 reviews

Cherokee Park Oasis with Private Entrance

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.

An outdoor courtyard space features colorful murals on a black brick wall. Comfortable seating areas with modern benches surround fire pits. A cowboy pool and hot tub are positioned alongside a basketball court, with vibrant green grass completing the inviting, communal atmosphere.

4.91 out of 5 average rating, 69 reviews

ꕥEntire Triple CrownꕥSlps 18, HOT TUB, POOL, firpt

Triple Crown Building ⦾Crafted for the 'gram -Murals, amenities, style ⦾2 Floors, 6 bedrooms, 6 bathrooms -Master King ensuites, tiled bathrooms, modern kitchens, spacious common areas Entertainment courtyard ⦾HOT TUB, Cowboy POOL, Sauna, Outdoor bar & Firepits seating for 12 each, Grill, BB court, outdoor rainfall shower, putt putt, shuffle board, trash pong! Best location in the city! ⦾Between Highlands, 4th St Live, & NULU ⦾ 1.5 miles from YUM Center, Whiskey Row, hospitals ⦾ Free Parking

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

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 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.

5 out of 5 average rating, 120 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

Peppermint Cottage Norton Commons w Breakfast

Step into Peppermint Cottage and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville's excitement, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, and YMCA with pool. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and Friday food truck festivities. Your ideal Louisville adventure awaits at Peppermint Cottage!

4.89 out of 5 average rating, 62 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

Location! VIEW! LUXURY! POOL! 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!

A living area is characterized by a vibrant blue wall adorned with gold accents. A brown sofa is complemented by two armchairs, and a round table sits atop a colorful area rug featuring swirling patterns. Natural light enters through large windows, enhancing the space.

4.93 out of 5 average rating, 162 reviews

4th Street Suites - Splash 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!

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.

4.82 out of 5 average rating, 111 reviews

Spacious Riverfront Condo Minutes from Downtown!

Condo 12 minutes from Churchhill Downs, Perfect for Derby! 2-story townhome at The Harbours Condominiums directly across from Louisville overlooking downtown & the Ohio River! Indoor & outdoor pools & gym. Short walk to dozens of restaurants or take an easy stroll across the nearby walking bridge to downtown Louisville. 8.1 mi. to SDF Airport 6.7 mi. to Kentucky Expo Center 1.6 mi. to YUM Center 5.9 mi. Kentucky Fairgrounds/KY Kingdom 2.3 mi. to Louisville Bats Stadium 10 mi. to Zoo

A bright living area features a contemporary design with a light sofa adorned with decorative pillows, complemented by two stylish lamps. A geometric mural in black and gold accents the wall, while a round coffee table sits atop a patterned rug, enhancing the inviting space.

4.97 out of 5 average rating, 104 reviews

Chic Escape • King Bed, Pool, 24/7 Gym + Hot Tub

Enjoy all of what Louisville has to offer with this luxury apartment perfect for 4 guests! With a comfortable memory foam king size bed and a memory foam sleeper sofa, you can enjoy a peaceful nights sleep and wake up to complementary coffee and a sunrise over the city skyline! Enjoy the plethora of activities and restaurants all within walking distance, including 4th St. Live! End the day with a virtual golf game, hit the gym, or relax with a movie. Book your stay with us today!

4.97 out of 5 average rating, 260 reviews

A spacious backyard is illuminated by string lights at dusk, featuring a hot tub and multiple seating areas around a fire pit. The well-maintained lawn and patio area create a welcoming outdoor space for relaxation and gatherings.

Home in Schnitzelburg

5 Baths• King Beds• Hot Tub • Expo & Bourbon Trail

• 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.

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.

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.

4.77 out of 5 average rating, 26 reviews

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!

4.9 out of 5 average rating, 21 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.

Flat 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!

Popular amenities for Central Business District 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.

4.68 out of 5 average rating, 59 reviews

Louisville KY Home w/Hot Tub & Pool

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

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.

5 out of 5 average rating, 7 reviews

A serene backyard features a chemical-free pool bordered by lush greenery and walking paths. Two lounge chairs provide seating areas for relaxation. The home’s exterior is visible in the background, complemented by a cloudy blue sky and clear sunlight.

Home in Jeffersonville

Urban Lakeside 3BR Retreat w/ Private Pool

Home in Jeffersonville

New place to stay

Rock & Roll Riverhouse | Pool | Mins to Louisville

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

5 out of 5 average rating, 46 reviews

A charming fountain features a statue atop its structure, surrounded by gently flowing water that creates a serene atmosphere. In the background, a modern brick building is visible, with well-lit windows and landscaped greenery, enhancing the inviting ambiance of the area.

Home in Prospect

No Guests Fees, NEW, Bourbon, Horses, Golf Nearby

Other holiday 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.

4.91 out of 5 average rating, 145 reviews

4th Street Suites - Comfortable 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, 265 reviews

4th Street Suites - Luxury King Bed Suite

A modern living area features a light gray sofa adorned with decorative pillows and a plaid throw blanket. Two red armchairs complement the space, which is anchored by a dark coffee table. A colorful piece of wall art and large windows allow natural light to fill the room.

4.98 out of 5 average rating, 158 reviews

Downtown Getaway • King Bed, Heated Pool + Hot Tub

A bright bedroom features a spacious bed with a red throw blanket and neatly rolled towels. Two bedside tables with stylish lamps flank the bed. Three abstract art pieces hang on the wall above, while large windows provide natural light and a view of the outside.

4.92 out of 5 average rating, 121 reviews

Modern Apartment• King Bed, Heated Pool + Hot Tub!

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, 141 reviews

4th Street Suites - Stunning King Bed Suite

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, 286 reviews

4th Street Suites - Ali King Bed Suite

A modern bedroom features a cozy king bed with soft linens, a comfortable sofa, and a patterned area rug. Natural light filters through the large windows, with a green plant adding a touch of nature. Soft lamps provide additional lighting, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 303 reviews

4th Street Suites - Deluxe King Bed Suite

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.