Vacation rentals with a pool in Oldham County

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Top-rated rentals with a pool in Oldham County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A well-arranged bed features a neutral-toned knitted throw and decorative pillows with unique shapes. A wicker tray in the center holds a bottle of champagne and four glasses, accompanied by two plates and napkins, creating an inviting setting.

Home in Prospect

5 out of 5 average rating, 109 reviews

Stay@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!

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

4.75 out of 5 average rating, 12 reviews

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.

Top guest favorite

An aerial view captures the spacious property surrounded by lush greenery, featuring a heated saltwater pool and an inviting firepit area. The home presents a modern façade, complemented by soft evening light as the sun sets, creating a serene outdoor retreat.

Home in La Grange

4.98 out of 5 average rating, 57 reviews

Fall Escape: Heated Pool, Hot Tub, Fire Pit, Pets

✨ 8 ft. deep-end saltwater pool, safety autocover, and optional *heat; ✨ Outdoor paradise: 6 lux lounge chairs, al fresco dining for 12, charcoal grill, hammock, cornhole, bucket golf, space to play ✨ Hot tub, Karaoke, Fire pit, garage games (pool, foosball, poker), basement arcade games, board games & outdoor games ✨ Four bedrooms, 5 king beds, and a 🛋 sofa sleeper in speakeasy (sleeps 12 total) 🐾 Pet Friendly ✨ 5 Minutes to grocery & Gas ✨ Stocked chef's kitchen ✨ 10 min to DT La Grange

Top guest favorite

An aerial view showcases a spacious house surrounded by greenery, with a swimming pool in the foreground. The pool is set in a concrete deck area, complemented by neatly kept lawns and trees. The clear blue sky adds to the serene atmosphere.

Farm stay in Simpsonville

5 out of 5 average rating, 33 reviews

4BR Farm~Bourbon Trail~private pool~horses

Sabre Hill Farm house rental is the perfect place to immerse yourself in the relaxing sounds of nature. On the 25 acres you will find all the comforts of home on a farm with horses, goats and mules. It is ideally positioned as home base for both indoor & outdoor activities including Derby & Horse Events, group gatherings &/or bourbon tours. Between activities unwind on the veranda or pool overlooking the horse paddocks. Pool includes May thru Oct. Horse boarding and arena use options.

Top guest favorite

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

5 out of 5 average rating, 27 reviews

NEW Golf, Horse, Bourbon, Pool, Downtown, Pets

*Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required* Find your ultimate spring retreat at Norton Commons! This charming home connects you to downtown Louisville, Bourbon Trail, horse country, and nearby attractions. Great for families or groups, relish dining downstairs, walk around & browse boutique shops, & dive into community perks. Steps from distilleries, and stunning horse farms! Book today for a Kentucky trip you’ll treasure!

Guest favorite

A cozy living room is featured, showcasing a large sectional couch and a flat-screen TV on a sleek stand. Built-in shelves with colorful items provide visual interest, while a fireplace offers warmth. Natural light illuminates the soft carpeted floor, enhancing the space's inviting feel.

Townhouse in Louisville

5 out of 5 average rating, 25 reviews

Safe, scenic, convenient. Bordering a State Park!

Located in one of the safest parts of Louisville, this place is conveniently located by shops, restaurants, parks, and a movie theater, and only a few minutes from a major highway. Walk right out to the beautiful Tom Sawyer Park. Park features free to use nationally recognized BMX bike track, 6 tennis courts, 16 pickleball courts, a playground, an archery range, walking trails, shelters, and even an Olympic size pool with a splash ground (small entrance fee for pool and splash ground.)

Guest favorite

A circular outdoor pool is surrounded by a spacious deck and bordered by lush green trees. A slide is visible at one side, and several pink lounge chairs are arranged nearby, offering a relaxing spot to enjoy the serene landscape.

Guesthouse in Pendleton

4.88 out of 5 average rating, 72 reviews

The Waterfall Place, Suite and Walkout!

Get the double deal! The Waterfall Walkout (Sleeps 10+) + The Waterfall Studio Suite! (Sleeps 4+) PLEASE NOTE: This is a listing for the Walkout and Suite ONLY. It does not include the upper floor or the rest of the middle floor. Located only 35 minutes from downtown Louisville and Madison, Indiana. Relax in a country setting with serene nature! Perfect for LARGE groups, family vacations, or just a simple getaway! Welcome to Oldham County We look forward to hosting your stay!

Guest favorite

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

5 out of 5 average rating, 39 reviews

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.

Top guest favorite

A serene view captures a shimmering private pool surrounded by lush landscaping. The tranquil river flows gently in the background, dotted with trees and open fields under a partly cloudy sky. Comfortable lounge chairs are positioned by the pool for relaxation.

Home in Goshen

5 out of 5 average rating, 68 reviews

Relaxing River Retreat with Private Pool

Beautiful river front vacation-like home with sparkling private pool and gorgeous landscaping for enjoying Oldham County's natural beauty. Pool has plenty of space to splash while enjoying the river view (pool is open from April through October, and is not heated). NOTE: This is NOT a party house. Parties are not allowed. Home is protected with ring cameras. Must be 25 years old to rent, per Oldham County regulations.

Top guest favorite

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

5 out of 5 average rating, 8 reviews

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!

Top guest favorite

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

5 out of 5 average rating, 22 reviews

CIRCO LOCO - uNCommon Stay

Circo Loco is a fun getaway where any idea is welcome, there is not one too wild. Circo Loco invites you to come embark on a circus adventure of a lifetime. With free access to beautiful community pools, countless parks, and an endless number of unique opportunities in the Norton Commons & Louisville area- we promise you won't be disappointed staying here. This unique place has a style all its own.

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.

Home in Louisville

5 out of 5 average rating, 9 reviews

Home Baby Home

5 bedroom, 3.5 bath, finished basement. Huge open backyard with screened in porch. Dog Friendly. Enjoy the big backyard that has a trampoline, basketball hoop, large fire-pit area & screened in porch that has ring toss, cable tv with sitting area & granite high top table to play games around or dine together. Plenty to do inside as well including pop-a-shot, theater room & tons of board games.