Holiday rentals with a pool in Clarksville

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, 68 reviews

An inviting outdoor space features a spacious in-ground pool surrounded by a decorative fence. Lush green trees provide shade, while the backdrop showcases a sunset sky with soft purple hues. Comfortable lounge chairs are positioned near the water, enhancing the area's relaxing ambiance.

Home in Mount Washington

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

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, 71 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.

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

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 and cabana with wet bar. 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.

Flat in Central Business District

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, 270 reviews

4th Street Suites - Ali 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.

Flat in Central Business District

A cozy living area is featured with a large light-colored sofa adorned with various decorative cushions. Two lamps sit on either side of a wooden coffee table, which displays a decorative "hello" sign. Three wall art pieces showcasing plant designs are displayed above the sofa.

4.95 out of 5 average rating, 120 reviews

Chic Apt – Heated Pool & Hot Tub Near 4th St Live!

Enjoy all of what Louisville has to offer with this luxury apartment perfect for 4! With a king memory foam bed and a queen 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!

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.

Home in Jeffersonville

4.75 out of 5 average rating, 88 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

Popular amenities for Clarksville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A split-level home is displayed, featuring a combination of brick and siding. A well-maintained garden with vibrant flowers lines the front. A mature tree provides shade, and the house is accented with dark shutters beside the windows. A welcoming sign is visible in the yard.

4.96 out of 5 average rating, 24 reviews

The Getaway!

Superhost

New place to stay

The Ville Getaway! Centrally Located

4.96 out of 5 average rating, 23 reviews

The living area features plush seating arranged around a round wooden coffee table. Light streams through multiple windows covered with sheer curtains, highlighting the warm tones of the decor. A large flat-screen television is mounted on the wall, providing modern entertainment options.

Home in Prospect

NEW Pet Friendly, Shops, Downtown, Norton Commons

A modern kitchen area displays a wooden counter with storage drawers beneath. Above, a reclaimed wood shelf houses an assortment of books and decorative items. Two mini-fridges are positioned under the counter, enhancing functionality. A potted plant adds a touch of greenery to the space.

5 out of 5 average rating, 56 reviews

Countryside Getaway

4.95 out of 5 average rating, 21 reviews

A welcoming exterior of a home features a covered front porch with two chairs and potted plants. Decorative shrubs and trees provide greenery, while the gray siding and white trim present a classic appearance. The front door is framed by large windows, enhancing natural light.

Home in Schnitzelburg

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

4.86 out of 5 average rating, 21 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

4.99 out of 5 average rating, 74 reviews

A serene river view is captured at sunset, showcasing a vibrant sky with purple and orange hues reflected in the calm water. Lush green foliage borders the riverbank, creating a peaceful natural setting.

Home in Goshen

Relaxing River Retreat with 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

Other holiday rentals with a pool

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.

Flat in Prospect

Acadia II Apt. in the Commons

The exterior of the two-story home presents a wooden deck with stairs leading to a grassy yard. The light-colored siding and large windows create an inviting appearance. Red outdoor chairs are positioned nearby, contributing to the outdoor space's usability and charm.

Home in Beechmont

4.5 out of 5 average rating, 6 reviews

Rye Retreat | Churchill | Expo

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

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.

Flat in Central Business District

Luxury, Modern 1-Bedroom High Rise Condo

5 out of 5 average rating, 13 reviews

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

Charming & Cozy Cottage in Quiet Neighborhood

A spacious house is set on a well-maintained grassy area, framed by trees in the background. A circular driveway leads to the entrance, where manicured shrubs and flower beds provide a natural touch. The home's neutral façade and stone accents blend harmoniously with the surroundings.

5 out of 5 average rating, 4 reviews

Southerland Vacation Home

A charming pink house with multiple levels is featured, presenting a classic architectural design. A spacious porch, framed by white railings, invites gatherings. A sign labeled 'Pink Castle' is positioned nearby, and the vibrant exterior is complemented by lush green grass and a clear blue sky.

Home in Jeffersonville

Pink Castle Babe’cation of Indiana!

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.