Holiday rentals with a pool in Central Business District

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, 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.

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, 186 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, 119 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!

4.88 out of 5 average rating, 59 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 Water-front studio is your perfect home for your Family or Business trip. Great place for The Kentucky DERBY, Thunder, Bourbon & Beyond. Walking distance to restaurants, Big four station, walking bridge to Louisville Downtown, great Bars,and nightlife. It’s just a short drive to Concert Venues, KFC YUM Center, EXPO center, Amusement Parks, hiking trails and the Bourbon trail. Make this your home for an Amazing Stay in Kentuckiana!

4.89 out of 5 average rating, 73 reviews

Flat in Prospect

Cozy Cottage in Smithsonian's of American Gardens!

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.

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

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

*Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required* Germantown is a unique blend of past and present. Restaurants and local attractions including Monnik Beer Company and historic Nords Bakery just blocks away from the home, there is something for everyone. Conveniently located within reach of several desirable destinations - The University of Louisville, Churchill Downs, downtown Louisville and the NuLu district nearby.

4.95 out of 5 average rating, 21 reviews

Home in Schnitzelburg

Germantown Gem - 3BR/2BA Home with Stock Tank Pool

This 3BR/2BA fully renovated home is in the heart of Germantown and close to the Highlands, KY Expo Center, Churchill Downs, UL, and Downtown Louisville! Ask about monthly discounts! • 3 Queen Beds • 2 Full Baths • Office with Monitor/Printer • Smart TV in Living Room and Projector with Apple TV in Primary Suite • Stock Tank Pool and Fire Pit in Backyard • Walk/Bike Score 75 ('Very Walkable/Bike able') • Fully Equipped Kitchen • Washer/Dryer • Coffee Shops, Restaurants, and Bars Walkable

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.

4.85 out of 5 average rating, 110 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 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, 145 reviews

Chic Apt – Pool, Hot Tub, Gym & Golf Simulator!

Live in luxury while being in the heart of it all! This centrally located space has all of the amenities and ambiance for a lavish getaway! Enjoy a peaceful nights sleep on a king bed, and wake up to a complementary cup of coffee! Get a workout in at our state-of-the-art gym, or explore everything Louisville has to offer right from your doorstep! With tons of bars, restaurants, live music, and other activities within a block, you'll never be bored! Book your stay with us today!

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.

4.91 out of 5 average rating, 195 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!

5 out of 5 average rating, 47 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.

Superhost

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.

Guest house in Louisville

4.76 out of 5 average rating, 25 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!

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.

Home in Louisville

4.67 out of 5 average rating, 57 reviews

Louisville KY Home w/Hot Tub & Pool

Superhost

Home in Louisville

New place to stay

The Ville Getaway! Centrally Located

5 out of 5 average rating, 5 reviews

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, 35 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.

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

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.

Home in Louisville

4.69 out of 5 average rating, 87 reviews

Spacious 5BR Getaway – Pool, Patios & Fun

5 out of 5 average rating, 43 reviews

A spacious outdoor area is equipped with a large dining table surrounded by woven chairs, offering a comfortable setting for meals. The deck provides a view of the neighborhood, with cars parked below and homes in the background. Natural light creates an inviting space for relaxation.

Home in Prospect

NEW Bourbon Trail, Downtown, Modern, Pets, Shops

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, 135 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, 255 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, 148 reviews

Downtown Apt – King Bed, Hot Tub, Pool & Parking!

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, 116 reviews

Elegant Apt – King Bed, Heated Pool, Gym + 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.

4.95 out of 5 average rating, 132 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.

4.91 out of 5 average rating, 272 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.

4.9 out of 5 average rating, 293 reviews

4th Street Suites - Deluxe King Bed Suite

Superhost

A spacious living area is depicted, featuring a comfortable gray sofa with decorative pillows positioned next to a side table. A modern kitchen with sleek cabinetry and stainless steel appliances is visible in the background. Large windows allow for ample natural light, illuminating the wood-style flooring.