Apartment holiday rentals in Southern Indiana

The Main St. Oasis - Heart of Downtown Madison

Welcome to the Main St. Oasis in the heart of Historic Downtown Madison! We're steps away from Lanthier Winery, shopping, fine dining, the Ohio River, have a coffee shop right across the street, and a flower shop beneath you! Close to Clifty Falls State Park (3 min) & Hanover College (9 min). Enjoy a unique retro-western theme, with games & luxuries for all ages. Perfect for couples, families, or small groups. Ideal for exploring Madison’s top attractions or relaxing in comfort right on Main St!

Value · Location · Pets

French Lick, Luxury Downtown Suite 315

This cozy, newly remodeled townhouse apartment is perfect for a family getaway, bachelorette/bachelor parties, or even your next golf trip. Centrally located in downtown in French Lick, IN. Directly across the street from the French Lick Resort & Casino! Accessible parking, within walking distance to shops, restaurants, and bars. Stay with us and receive 10% off your meal at Legendz Sports Bar & Grill, open seven days a week and features live music/karaoke and DJ every Friday & Saturday night.

Location · Value · Check-in

Stablemaster’s Quarters/ Best downtown location!

Come see why the city awarded us with the “Stellar Award”, Best Place To Stay in Madison! The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, laundry room & a furnished white kitchen will all be appreciated. Yet, historic charm remains. You will soon see why the entire building has won multiple awards. Come see why US Today awarded Madison “ Best Small Town in the Midwest”.

Value · Family · Wi-Fi

Urban Bourbon Stay - Nulu 2 BR * 2 Full Bath

Beautifully renovated historic 2 bedroom 2 full bath apartment in Louisville's hip Nulu neighborhood. Huge 1,500 sq ft space to relax in after enjoying all the shops and restaurants in the Nulu area. This apartment is just a few blocks east of downtown. It's a great area to kickoff your Louisville adventures. This apartment is above a boutique wine and bourbon shop and within walking distance of several distilleries, so you don't have far to go to sample some of Kentucky's legendary bourbon.

Value · Location · Checkout

Luxe speakeasy-inspired condo in the heart of NuLu

Welcome to Luxe Louis! Our home is a stylish art deco retreat with a moody and eclectic speakeasy vibe, sleeping 4 and perfectly situated for an unforgettable Louisville experience. A short walk from Whiskey Row, the Louisville Slugger Museum, and UofL, with Churchill Downs a quick ride away. Located in the vibrant East Market District (NuLu), enjoy unique art galleries, specialty stores, antique shops, and a renowned culinary scene. Embrace the spirit of Louisville in style at Luxe Louis!

Family · Location · Checkout

Lil BUB's Really Nice Apartment - EAST

We are conveniently located within walking distance of Downtown, Bryan Park, and The B-Line Trail, 1 mile to IU Campus, 1.8 miles to Assembly Hall, and 3.5 miles to IU Hospital. Our beloved luxury apartment is one of the nicest places to stay in town. It underwent a ground-up bespoke renovation with white oak hardwood floors, quartz countertops and premium appliances, rivaling a premium suite at a boutique hotel with the added privacy, charm, and amenities of a home for a great price.

Family · Value · TV

Ellie's Escape - In Historic Corydon, IN

Ellie's Escape is named for our oldest daughter who loves to travel. She has traveled with us since she was an infant and will pick up in a moment's notice to hit the road. This completely renovated and updated 1 Bedroom ground floor apartment is part of a historic home built in 1900. At nearly 1,000 square feet, it is much larger and certainly more comfortable than your typical hotel room. Located in the downtown historic district, it is walking distance to shops, restaurants and more.

Family · Value · Getting around

The Bardstown-Louisville Nightlife

This spacious unit provides a front row seat to watch and experience Louisville from the comfort of your own private retreat in the middle of the best street in Louisville. Feet from many restaurant , bars and boutiques. During your stay spend time walking the neighborhood filled with boutiques, restaurants, bars, distilleries and art galleries. Start the bourbon trail or walk to the famous Cave Hills Cemetery. Private gatherings are allowed but house rules must be followed.

Value · Family · Pets

Luxury Downtown Apt: 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.

Value · Family · Access

Steps to Whiskey Row | Historic Corner Loft

Immerse yourself in the heart of Louisville's celebrated bourbon culture with a stay at a beautifully restored historic loft located on the iconic Whiskey Row. Perfectly positioned on West Main Street, this spot is an ideal base for both relaxation and adventure. Just steps from Louisville's major event centers and distilleries, blocks from Museum Row, and less than a mile from the trendy NuLu Arts District, there's no shortage of entertainment for any traveler.

Location · Value · Walkability

Location! Corner downtown condo!

Welcome to your stylish urban retreat in the heart of downtown Louisville! This studio corner unit condo boasts modern amenities and stunning city views through floor-to-ceiling windows. With an updated bathroom and kitchen, plus a location within walking distance to the KFC YUM Center, shops, and restaurants, this condo offers the perfect blend of comfort and convenience for your stay in Louisville. Book now and experience the best of Louisville living!

Location · Value · Laundry

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful trees. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Family · Value · Decor