Holiday rentals with a pool in Jefferson County

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.

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 Condo in Louisville/Jeff

Location! Waterfront! Amazing Views! This newly renovated, Luxurious Riverfront condo is the perfect spot for your Family or Business trip. Ideal for the Kentucky DERBY, Thunder, and Bourbon & Beyond. Walk to restaurants, Big Four Station, the bridge to Downtown Louisville, great bars, and nightlife. A short drive to major venues, the KFC YUM! Center, EXPO Center, amusement parks, hiking trails, and The Bourbon Trail. Make this your home for an Elevated Stay in beautiful, vibrant 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.

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

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.

Downtown Getaway • King Bed, Heated Pool + Hot Tub

Stay in style and comfort while enjoying everything this apartment has to offer. Rest easy on a comfortable mattress, then start your morning with a complimentary cup of coffee. Work out in the gym , relax on the rooftop, or step outside to explore downtown just moments away. With dining, entertainment, and activities all around you, there’s always something to do. Wind down with a glass of wine and a movie on Hulu or Disney+, then book your stay and enjoy it all.

Peaceful Hillside Guest Suite - Private Entrance

Discover a secluded countryside escape, 15 minutes from the city of Louisville. The lower level walkout guest unit features a private entrance, an open-plan living area, a kitchen and bar, large patio, and access to the pool. Amenities include: • 65” TV in living room area with streaming services • Laundry Room with washer & dryer • Queen size sofa sleeper with memory foam mattress • Stovetop, refrigerator, microwave, toaster oven with air fryer • Ping Pong Table

Cozy & fun Studio Near Churchill Downs/Fairgrounds

✨ Kick back in our bright and comfy studio on a peaceful 3-acre property! Just minutes from Churchill Downs, the Fairgrounds (perfect for concerts!), Iroquois Park, and downtown Louisville. Enjoy beautiful views, pool access, and even free training at our fitness gym. Ideal for event-goers, concert lovers, or anyone looking for a laid-back, unique stay. ☕ Grab a coffee on the back patio in the morning — you might spot our friendly family of deer wandering by!