Holiday rentals with a pool in Louisville

Cherokee Park Oasis with Pool and Hot Tub

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.

Luxury Retreat with Hot Tub

Welcome to Four Seasons Cottage on the Bourbon Trail! This charming property is located in a peaceful vacation community, just a short walk from the seasonal pool. Featuring 2 bedrooms, a fully equipped kitchen, and cozy living room with a fireplace, this cottage is perfect for a family getaway or a couples retreat. Enjoy the large deck with a hot tub and BBQ, as well as access to nearby hiking trails and attractions. Cottage 37 sits on a ridge that overlooks the 3,050-acre Taylorsville Lake.

LUX Riverfront Studio Louisville/Jeffersonville

Location! VIEW! ! DERBY! This Newly renovated, Luxurious Waterfront Studio is the perfect home for your Family or Business trip. Ideal for The KENTUCKY DERBY, Thunder, and Bourbon & Beyond. Enjoy walking distance to restaurants, Big Four Station, the bridge to Downtown Louisville, bars, and nightlife. It’s also a short drive to Concert Venues, the KFC YUM Center, KY EXPO Center, Amusement Parks, Hiking Trails, and the Bourbon Trail. Make this your home for an Amazing Stay in Kentuckiana!

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

Explore Jeffersonville & Louisville/Book for Derby

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 our photos & read the descriptions under them. You’ll love our home because we are close to downtown Louisville & Jeffersonville yet tucked away enough for a peaceful, relaxing stay. No early check-ins allowed.

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!

Sleeps 16, Heated Pool , Hot tub, Close to Dwtn

5000 square foot house set on a beautiful lot backed to a nature reserve park. Total of six bedrooms, three and half bathrooms. 5 large bedrooms with 5 queen beds each, 3 singles on the second floor and a mother-in-law suite with a king size bed and a single bed on the first floor. pool and hot tub. Pool is open from May 15 to October 15 and will be heated from Sep 15 to Oct. 15. Inflatable Water Slide is upon request. Gas grill on the deck and propane tank is available.

6 BR Highlands- King Beds- 2 Kitchens-Walkable

• 6 King Beds, 1 Queen & 2 twin pullouts • 2 Fully equipped + stocked kitchens • Onsite, secured parking 6+ vehicles • 2 Living Rooms • 5 Bathrooms • 1/2 acre backyard 12min drive to downtown Louisville 10min drive to Churchill downs and Kentucky Derby Strictly no outdoor deck use/noise after 10pm *Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required* *All guests required to to sign a rental agreement*

No Guest Fees, Pet Friendly, Bourbon, Downtown

Your perfect retreat in Norton Commons, Prospect, KY! This home is steps from Glen Oaks Country Club and offers easy access to the Bourbon Trail, horse farms, and local dining. Enjoy community amenities like parks, live entertainment, and the YMCA with its gym and indoor pool. With 4 bedrooms, 2 baths, and proximity to distilleries, horse farms, and golf courses, this home is ideal for families and groups. Your Kentucky adventure starts here—book now!

Louisville KY Home w/Hot Tub & Pool

Come celebrate the holidays Kentucky style! Bring the whole family to our beautiful 4-bedroom - We can even host your family holidays! (One room in basement with no egress), 3-bathroom Louisville retreat with a Pool (open May-Oct), Jacuzzi Spa (Year round), Mini Gym with Dumbbells, and Recreation room with other amenities. The entire house is open for your experience. Kid and Family friendly, this guest favorite home is what you've been looking for.

Heated Saltwater Pool Estate, Hot tub, Games

For families who want a private resort, not just a place to sleep. A 3.75-acre estate with a heated pool and safety cover, two game rooms, and space for everyone to be together & apart—thanks to two wings. Sleeps 12. Five king beds. No one compromises. Just 25 min to Louisville and the Bourbon Trail. Scroll down—karaoke, night swimming under the lights, and a quiet piece of Kentucky history tucked into the property you won't find anywhere else!

Chic Escape • King Bed, Pool, 24/7 Gym + Hot Tub

Experience Louisville in style from this upscale apartment, perfect for up to 4 guests. Sleep easy on a plush king memory-foam bed or queen memory-foam sleeper sofa, then start your morning with complimentary coffee. Step outside to walkable dining, entertainment, and 4th St. Live! Wind down with virtual golf, the 24/7 gym, or a movie night with Hulu and Disney+. Comfort, convenience, and a true city experience book your stay with us today!