Apartment holiday rentals in Southern Indiana

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Derby Weekend Retreat | Designer Curated Stay

A thoughtfully curated stay by Jaclyn Journey Hospitality, designed with intention so you feel cared for while away from home. Set within a historic 19th-century building, the space celebrates character & charm while offering beautifully considered comforts throughout. Featured in Architectural Digest, DOMINO Magazine, Apartment Therapy, & more. Every detail has been hand-selected to delight the senses. The apartment is also shoppable, inviting you to take home a favorite piece of your stay.

Stylish groovy condo minutes from Churchill Downs

Welcome to Groovy Louis, a funky and eclectic condo in Louisville’s vibrant NuLu district. Sleeping up to 4 guests, this stylish retreat is just a short walk from Whiskey Row, the Louisville Slugger Museum, UofL, and a quick ride to Churchill Downs. Explore art galleries, antique shops, specialty stores, and one of the city’s top culinary scenes right outside your door. With modern amenities and unique charm, Groovy Louis offers the perfect blend of comfort, culture, and convenience. Book now!

Falls City Loft - Free parking!

If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft https://www.airbnb.com/h/bourbon-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Convention Center, and 10 minutes from Churchill Downs! Free parking in a secured parking garage.

Downtown Nashville's Hidden Gem!

This location cannot be beat! Downtown Nashville, Indiana above all the shopping you will find this modern 2nd floor apartment that is truly a hidden gem. Minutes away from the Brown County Music venue. You will feel at home with a full size kitchen, a balcony with scenic views, gas grill, and a private entrance. The entire floor is yours to enjoy. Best feature may be the oversized master suite w/ private seating. The living room also offers a futon style sofa so bring a friend or two!

Studio Apartment w/ Beautiful View!

Come and stay a while in this charming and unique studio apartment. Located in the heart of historical Aurora, IN, you can walk to all the shops, parks and restaurants! Step out onto your private patio and enjoy your view of the Ohio River! It’s the perfect romantic getaway. We are also pet friendly so if you want to bring your furry friends we are happy to host them as well, just be aware that there is a $100 fee that covers our additional cost. Just add them with your guests at checkout.

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

Ruby's Retreat- In Historic Downtown Corydon, IN

Ruby's Retreat, named for our younger daughter, is a NEWLY RENOVATED 2 Bedroom, 1 Bathroom upper level apartment. It's perfect for small groups, couples, or business travelers. It's much larger and certainly more comfortable than your typical hotel room. Located in the downtown historic district, it's walking distance to dining, shopping, and more! As avid travelers, we strive to offer THE BEST experiences for short and long-term stays. We look forward to hosting you! 

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!

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 hills of Kentucky. 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.

Hidden Cottage on Main over Ooey Gooey Café

You'll love staying just out of the center of town for a peaceful retreat with easy key code check-in. Walk anywhere in town, taking advantage of all the restaurants and shopping. Wake up to the smell of the Ooey-Gooey cinnamon roll cafe downstairs. With a 2-night stay, enjoy a cinnamon roll on us (closed Monday and Tuesday) Explore beautiful Brown County and have a comfortable bed to come home to at the end of the day, just how vacation should be.

Sun-filled Phoenix Hill Studio

Located in the Phoenix Hill neighborhood, it's a short 11 minute walk to East Market District restaurants and attractions or a 15 minute walk to Gravely and other Original Highlands destinations. 11 minute drive to Churchill Downs 5 minute drive to the Highlands 4 minute drive to East Market restaurants and shopping. Ample Lyft and Uber drivers in this neighborhood to take you anywhere you want to go. .