Villa holiday rentals in Southern Indiana

The Harmony House Aurora

Harmony House is a historic Victorian villa in Aurora, Indiana where people can find lodging and gathering space for family trips, retreats, and special occasions. It is a place of peace, warmth and welcome where folks can come to experience rest, reflection and renewal where family, friends and neighbors can gather to enjoy time together and build community; where outoftown guests can come to explore the quaint river town of Aurora as well as attractions in Cincinnati, northern Kentucky area

Industrial Elegance-Mass Ave-Free Parking-Events

In the heart of the Mass Ave cultural district, this impressive home offers a refined high-end design and city feel. Take in the grandness with natural light from the second-story sidelights, gorgeous exposed woods, and beautiful heated Italian tile floors. The large scale great room encompasses living, dining, and an open contemporary kitchen. The grand hall leads to two large bedrooms with private bathrooms. Complete with a charming private courtyard. Luxury you may never want to leave!

Secluded & Luxury Haven ~ Trails ~ Gym ~ Pets OK!

Indulge in this luxurious 4BR 2.5Bath villa nestled on a secluded 50+acre plot near Bloomington and Nashville, IN. This spacious property offers the perfect retreat from bustling crowds with its trendy design, high-end comforts, contemporary amenities, and scenic views from the magical pergola. ✔ 4 Comfortable Bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Movie/Game Room ✔ Gym ✔ Workspace ✔ Outdoors (Pergola, Fire Pit, Lawn) ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking Learn more below!

Villa On the Bourbon Trail with HOT TUB-3

Escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail, nestled on a private farm, perfect for making memories that will last a lifetime. Featuring A king and queen bed Full kitchen for effortless in-cabin dining Private hot tubs to soak in after a day exploring distilleries Scenic views of the countryside from your private back porch Convenient location to Lexington, Louisville, Frankfort, and Danville and a short 20 minute drive to Bluegrass Airport.

Bourbon Villa at Daynabrook Farm with HOT TUB-5

Escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail, nestled on a private farm, perfect for making memories that will last a lifetime. Featuring A king and queen bed Full kitchen for effortless in-cabin dining Private hot tubs to soak in after a day exploring distilleries Scenic views of the countryside from your private back porch Convenient location to Lexington, Louisville, Frankfort, and Danville and a short 20 minute drive to Bluegrass Airport.

Modern 3 BD/3.5 BA Newer Construction!

Enjoy a stylish experience at our modern new construction home. Every detail was masterfully thought out during construction to ensure each bedroom was accompanied with its own bathroom and spaces were maximized for comfort. Our beautiful home is just blocks away from some of the best bars, restaurants, and entertainment hubs in the city! Grab a scooter to jet around town or take a peaceful morning walk along the riverfront or across the walking bridge. Our Derby City Escape has it all!

12acre Villa right by Keeneland-Keene Creek Estate

10,000sqft Villa on 12 acres of gorgeous Kentucky countryside! Located less than a mile from Keeneland with access to Back Gate Drive. The estate is surrounded by horse farms and has nearly 300yds of creek frontage, a forested preserve, and rolling green pastures. We allow 8 vehicles and up to 19 guests. Please note we are only allowed to host up to 4 unrelated individuals at a time, as per Fayette County rules. So, this property is great for large family get togethers!

Historic Briar Rose Estate | Sleeps 16 |

Briar Rose Estate: An Opulent Getaway in the Heart of Shelbyville, KY Welcome to Briar Rose Estate, where luxury, serenity, and timeless beauty converge. Nestled on 50 acres of Kentucky’s rolling green hills, our meticulously restored estate offers a peaceful escape from the ordinary. Whether you're seeking a relaxing retreat, a cozy family getaway, or a special place to celebrate life's moments, Briar Rose Estate provides the ideal backdrop for unforgettable memories.

The Retreat - Private Pool-Spa-Firepit-Gameroom

The Retreat! Newly remodeled, peaceful and spacious place to unwind & create memories despite being amidst the city with families & friends. ✔ 17min to Indy downtown, 7min to Greenwood mall, 23min to Airport, 27min to Speedway ✔ Upscale, safe and quiet location ✔ Modern furnishings; one of a kind kids play room; Rec room for adults ✔ Resort living with private pool, hot tub, fire pit, BBQ ✔ 6 Smart TVs ✔ Fully stocked kitchen -baths ✔ Highchair, stroller, Pack N Play