Holiday rentals with a pool in Jeffersonville

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.

Relaxing River Retreat with Private Pool

Beautiful river front vacation-like home with sparkling private pool and gorgeous landscaping for enjoying Oldham County's natural beauty. Pool has plenty of space to splash while enjoying the river view (pool is open from April through October, and is not heated). NOTE: This is NOT a party house. Parties are not allowed. Home is protected with ring cameras. Must be 25 years old to rent, per Oldham County regulations. Please also note home is on 3 levels and requires going up and down stairs.

Lux Riverfront Condo in Louisville/Jeffersonville

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!

The Boathouse: A Peaceful Paradise

The Boathouse is located at the back of Tartan's Landing Marina off of the Ohio River. It sleeps up 7 people (1 king bed, 2 queen beds, 1 XL twin bed) has full kitchen and 2 full baths. Enjoy the infinity edge pool (open May-Oct), hot tub, outdoor fire pit, pickle ball area & private boat ramp (ARRANGEMENTS MUST BE MADE AHEAD OF TIME FOR A BOAT.) Heating the pool is optional for additional charge per day. All seasons are beautiful from the Boathouse located 30 min from downtown Louisville.

Exclusive Farmhouse w/ a Romantic Garden View!

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.

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 !

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 - Extravagant 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.

8 Min to Bourbon Fest | 6 Kings + Hot Tub

• 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

Modern DT Apt – Gym, Pool, Hot Tub & Golf Sim

Enjoy an elevated stay in this spacious one-bedroom apartment in the heart of downtown, just steps from everything Louisville has to offer. Start your morning with complimentary coffee, then hit the state-of-the-art gym or head out to explore. Walk to top restaurants, bars, live music, and entertainment including 4th Street Live! all right outside your door. Comfort, convenience, and location come together for a stay that’s easy and memorable. Book today.

Downtown->Heated Pool, Firepit, Bikes, Grill, Pets

🚨3/4/25 Pool is open year round and can get as hot as a hot tub! This historical beauty has many stories to tell but even more memories for guests to make. Less than 8 minutes away from downtown Louisville. The 3 bedroom 2 bath layout works is ideal for a traveling families or mid-size groups. The heated pool and fire table in the backyard provides endless entertain. Please note the pool heat is a $60/day charge and requires a weeks notice to schedule