Holiday 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 favourite
Home in Prospect
5 out of 5 average rating, 118 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!

Guest favourite
Home in Goshen
4.99 out of 5 average rating, 73 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. Please also note home is on 3 levels and requires going up and down stairs.

Guest favourite
Home in Goshen
4.86 out of 5 average rating, 21 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.

Guest favourite
Townhouse in Louisville
5 out of 5 average rating, 26 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.)

Top guest favourite
Home in Prospect
5 out of 5 average rating, 40 reviews

NEW Golf, Horse, Bourbon, Shops, Downtown, Pets

Welcome to your fall escape in the heart of Norton Commons! Watch Hill Manor is the perfect gateway to explore downtown Louisville, the Bourbon Trail, and rolling horse country. Enjoy crisp autumn days with a stroll to local shops, great dining, and community events right outside your door. The location also provides easy access to distilleries, scenic horse farms, golf courses, and seasonal activities like festivals and foliage tours. Book your memorable Kentucky getaway today!

Top guest favourite
Farm stay in Simpsonville
5 out of 5 average rating, 42 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 May thru Oct. heated 85*. Horse boarding available.

Flat in Prospect
New place to stay

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.

Top guest favourite
Flat in Prospect
5 out of 5 average rating, 47 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.

Guest favourite
Flat in Prospect
4.94 out of 5 average rating, 16 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 favourite
Home in Prospect
5 out of 5 average rating, 31 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.

Home in Louisville
5 out of 5 average rating, 10 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.

Guest favourite
Guest suite in Oldham County
4.79 out of 5 average rating, 78 reviews

WATERFALL WALKOUT HILLTOP SLEEPS 10+, 4 BR 2BA

Our Waterfall Retreat is an adorable 4 bedroom, 2 bath Hilltop Getaway Located only 35 minutes from downtown Louisville and Madison, Indiana. Relax in a country setting with serene nature! Perfect for individual travels, couples, family vacations, or just a simple get away! Welcome to Oldham County, KY. We look forward to hosting your stay!

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