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/Jefferson

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.

4th Street Suites - Ali 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!

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.

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!

Stylish DT Apt • King Bed, 24/7Gym, Pool + Hot Tub

This stylish, luxury apartment is ideal for couples, families, and small groups. Step inside to modern finishes, updated appliances, and thoughtfully designed décor with everything you need for a comfortable stay. Rest easy on a plush bed, then head out to explore Louisville top attractions, dining, and entertainment are just steps away. Prefer to stay in? Enjoy on-site amenities including a gym, rooftop access, and a golf simulator. Book your stay today.

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!