Holiday rentals with a pool in Jeffersonville

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 (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.

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.

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!

Cozy Cottage in Smithsonian's of American Gardens!

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.

4th Street Suites - Stunning King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

Germantown Gem - 3BR/2BA Home with Stock Tank Pool

This 3BR/2BA fully renovated home is in the heart of Germantown and close to the Highlands, KY Expo Center, Churchill Downs, UL, and Downtown Louisville! Ask about monthly discounts! • 3 Queen Beds • 2 Full Baths • Office with Monitor/Printer • Smart TV in Living Room and Projector with Apple TV in Primary Suite • Stock Tank Pool and Fire Pit in Backyard • Walk/Bike Score 75 ('Very Walkable/Bike able') • Fully Equipped Kitchen • Washer/Dryer • Coffee Shops, Restaurants, and Bars Walkable

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

Modern Downtown Apt – Pool, Hot Tub & Golf Sim!

Live in splendor on your visit to the 'Ville as you stay in this spacious one-bedroom apartment in the heart of downtown and all of the fun that Louisville has to offer! Wake up to a complementary cup of delicious coffee before enjoying a workout in our state-of-the-art gym or hit the town right from your doorstep, with tons of great restaurants, bars, live music at 4th St. Live, and plenty of other activities all within walking distance! Book your stay with us today!

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.

5 Baths• King Beds• Hot Tub • Expo & Bourbon Trail

• Spacious 5BR, 5BA home—great for groups • 1st floor: king bedroom + full bath in hallway • 2nd floor: two king en-suites + queen w/ hall bath • Walkout basement: two king beds w/ privacy curtains, full bath + living room • Hot tub • Fast Wi-Fi • Easy street parking • Minutes to Expo Center, Churchill Downs & Downtown • Derby, Bourbon & Beyond & Louder Than Life guests must inquire first, strict cancellation policy required. • Rental agreement + damage deposit required

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.