Villa holiday rentals in Southern Indiana

Historic Estate Pool/Hot Tub, Louisville Retreat

Explore the renowned KY Bourbon Trail or the excitement of the Louisville KY Derby, only 45 minutes away. An ideal retreat for adventure & relaxation. Nestled on 2.1 picturesque acres near the Ohio River, this elegant historical home harmonizes classic charm & modern luxury. Prime location, adjacent to the River Walk boat launch, offers convenient access to water activities. Outdoor enthusiast will appreciate nearby hiking & biking trails at Buttermilk Falls & Otter Creek. Private Pool/Hot Tub.

Bourbon Trail Firepit Hot Tub River Road Picnic

After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trail, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

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

The Tulip Tree Villa with Loft | Pet Friendly

Welcome to Lake Monroe Getaway! 🏡 This peaceful and charming villa nestled in Lake Monroe Village — just minutes from Indiana University. Surrounded by nature and tranquil scenery, this cozy retreat is the perfect place to relax, recharge, and admire the beauty of the outdoors. ✨ What You’ll Love • Private deck with comfy outdoor seating • Short drive to Lake Monroe & IU • Peaceful neighborhood ideal for long-term stays Your Bloomington nature escape awaits — book your stay today! 🌅

Bourbon Villa at Daynabrook Farm, Hot Tub-2

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm, Hot Tub-1

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm, Hot Tub-4

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm, Hot Tub-6

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm, Hot Tub-3

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm, Hot Tub-5

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Luxury Villa with Gym & Trails - Pets Welcome!

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!

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!