Holiday rentals with a pool in Jeffersonville

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.

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!

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!

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!

Farmers Market, Brewery, Bardstown 2 Decks & Porch

*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* • 5 King Beds, 2 Queen pullout, 3 twin beds • 2 Fully equipped + stocked kitchens • Onsite, secured parking 6+ vehicles • 2 - 65" TV's + 5 smaller TV's • 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

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

Norton, Bourbon Trail, Shops, Golf, Pets, Downtown

Experience Kentucky’s charm this fall from your Norton Commons retreat. Just minutes from downtown Louisville, explore the legendary Bourbon Trail, visit Churchill Downs, and tour scenic horse farms. From October 2 to November 2, stroll through the glowing Jack O'Lantern Spectacular at Iroquois Park. End your day with dinner at local restaurants just downstairs or relax in cozy comfort surrounded by vibrant autumn colors and friendly neighborhood energy. Book your autumn retreat now!

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.

4th Street Suites - Deluxe 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.

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.

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!