Vacation rentals with a pool in Oldham County

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. Please also note home is on 3 levels and requires going up and down stairs.

Location · Value · Long stay

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.

Location · Family · Laundry

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.

Family · Value · Check-in

4BR Farm~Bourbon Trail~private heated 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. Saltwater Pool May thru Oct. heated 85*. Wifi is NOT fast here

Family · Location · Grill

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.)

Family · Location · Quiet

Acadia II Apt. in the Commons

The Acadia II apartment is a 2,125 sf BRAND NEW second floor apartment with a terrace that overlooks the charming Norton Commons community in Louisville, KY. The apartment includes ALL new furniture, appliances, bedding, towels and kitchenware to make your stay comfortable and easy. Norton Commons is a mixed-used community featuring parks, use of pool (in season), special events and 100 walkable businesses including award-winning restaurants, bars, retail shops, and services.

Location · Cleanliness · Nearby

The Waterfall Walkout AND The Overlook Studio!

The Waterfall Walkout (Sleeps 10+) + The Overlook 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 on a 35+ acre estate setting, up close to a waterfall. Perfect for groups, family vacations, or just a simple getaway! Welcome to Oldham County We look forward to hosting your stay!

Location · Value · Parking

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.

Value · Family · Bathroom

Lux 3BR apt*Location

Welcome to this stylish 3 bedroom, 2 full bath luxury apartment centrally located in the highly sought after Crestwood area. Located just off I-71, this apartment is spacious and fully appointed. The kitchen is fully stocked and also offers coffee as well as creamers. 2 bedrooms have king beds; 1 king bedroom is an en-suite and 1 shares the full hall bathroom with the queen bedroom. This apartment is located on the 2nd floor of the building.

Family · Location · Amenities

Pet-Friendly Manor on Bourbon Trail, Pools, Golf

Escape to Norton Commons, Prospect, KY, and immerse yourself in bourbon culture, horse country, and golf! This 4-bedroom home is steps from Glen Oaks Country Club and offers easy access to community pools, distilleries, horse farms, and local dining. Enjoy community amenities like pools, parks, live entertainment, and the YMCA. Perfect for families and groups, this retreat is your base for an unforgettable Kentucky experience—book today!

Family · Location · Nearby

Norton Commons 4BR | Bourbon Lounge | Sleeps 10

Stay in the heart of Norton Commons at Delphinium Haus, a spacious four-bedroom retreat for up to 10 guests. Walk to neighborhood restaurants, coffee shops, and parks, then unwind in the private lower-level Bourbon Lounge with an 85-inch TV, Xbox, bar setup, and board games. A chef’s kitchen, multiple gathering spaces, and a main-floor king suite make the home ideal for family stays, wedding groups, and Bourbon Trail getaways.

Location · Family · Hospitality

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.

Value · Location · Pool