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.

Lake Refuge near Louisville & Bourbon Trail #52

Cottage 52 is a bright and comfy 3 bedroom/3 bath cottage, fully equipped and furnished with extras and a hot tub on the rear deck. This cottage offers a new hot tub, HD tv, and DirecTV with 200 HD channels. Cottage 52 sleeps up to 8 people and stocked with everything you will need to recharge. Escape the commotion and routine of the city, and immerse yourself in a new environment, surrounded by nature and wildlife. This lakeside cottage will have you forgetting about your worries in no time .

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 !

The Gathering Place

The Gathering Place is the perfect place to get away and gather with family and friends. The resort is located conveniently between Bardstown, Louisville, and Frankfort on the Bourbon Trail. Offseason hiking, fireplace, and hot tub make a great peaceful getaway or work from "home" experience. Enjoy fishing, boating, kayaking, hiking, bird/deer watching and relaxing. The owners have been Resort guests for years and now own a cottage to enjoy and share with family, friends, and guests.

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 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 - 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.

5BR w/ 6 King Beds + Hot Tub

• Spacious 5BR, 5BA home—great for groups • 1st floor: king bedroom + full bath in hallway • 2nd floor: two king en-suites + king 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

4th St Live | King · Pool · Hot Tub · Free Parking

Experience Louisville like a boutique hotel stay in the heart of downtown. This luxury apartment sleeps upto 4 with a king memory-foam bed and a queen memory-foam sleeper sofa for a restful night. Enjoy complimentary coffee and skyline views from your private balcony. Walk to dining, nightlife, and 4th Street Live!, then unwind with the heated pool, hot tub, golf simulator, gym, or a cozy movie night. Elevated comfort, prime location book your stay with us today.

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

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!