Villa holiday rentals in Southern Indiana

5 out of 5 average rating, 19 reviews

Villa in Brandenburg

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.

5 out of 5 average rating, 5 reviews

A modern kitchen features sleek stainless steel appliances, including a refrigerator and a gas stove. White cabinetry contrasts with dark accents, while marble countertops add elegance. Natural light is allowed through sliding glass doors, which lead to an outdoor space that can be seen in the background.

Villa in Indianapolis

Broad Ripple Villa (1 block to strip)

Welcome to the Broad Ripple Villa in the Village located in the HEART of Broad Ripple Village in Indianapolis; 1 block from some of the city's best pubs, restaurants, and local shops and 2 blocks to the Monon Trail. Plus with its central location you are less than 30 minutes from nearly all Indianapolis area events & attractions including the Convention Center, Lucas Oil Stadium, Gainsbridge Fieldhouse, The Children's Museum, & more. And don't miss the private swimming pool in the summer months!

4.95 out of 5 average rating, 242 reviews

The exterior of the villa features a rich burgundy facade and a welcoming porch with white railings. Lush green lawns and well-maintained landscaping surround the property. The charming architecture showcases multiple stories and large windows, enhancing the inviting curb appeal.

Villa in Indianapolis

Spacious Luxe Villa • Central • Up to 25 Guests

✨ Your Private Victorian Villa – Sleeps Up to 25 ✨ Renovated 1872 Villa on a quiet, tree-lined street in one of Indy’s top neighborhoods. 3 stories • 3 master bedrooms • 5 bedrooms • 4,000 sq ft • 4.5 baths • Chef’s kitchen Walk to Mass Ave, cafés & top-rated restaurants Perfect for family reunions, wedding stays, or retreats. Sip coffee on the porch, unwind in style—every corner crafted for comfort, space & peace. 🌟 Peaceful, central, and truly one of a kind—your perfect Indy stay begins here.

4.93 out of 5 average rating, 128 reviews

Villa in Prospect

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.

4.94 out of 5 average rating, 65 reviews

The exterior of Harmony House is showcased, featuring a historic Victorian design with bright yellow siding and intricate trim. A welcoming front porch is adorned with potted plants, while the unique round turret creates an eye-catching architectural detail. A sign identifying the property is visible in the foreground.

Villa in Aurora

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

A charming villa exterior is displayed, featuring a light-colored facade with multiple windows and a front porch. The surrounding greenery enhances the peaceful setting, while a white fence lines the front. A small storage shed can be seen on one side of the property.

Villa in Bloomington

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! 🌅

4.97 out of 5 average rating, 63 reviews

An open-concept living space is highlighted by natural light. A comfortable leather sofa faces a wooden shelving unit and a rustic sliding door. The kitchen area features a large island with seating for four, accentuated by light wood shelves adorned with decorative items.

Villa in Bloomington

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!

A modern cabin exterior is viewed from the front, featuring a large covered porch with two bright yellow chairs. The structure showcases a prominent peaked roof with wooden beams. Clear skies and green grass surround the home, enhancing its welcoming appearance.

4.92 out of 5 average rating, 91 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-2

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.

A newly constructed villa features a triangular roof and a front porch with wooden railings. Large windows are visible on the upper section, allowing natural light to illuminate the inviting entrance. The surrounding landscape appears lush and green under a clear blue sky.

4.96 out of 5 average rating, 85 reviews

Bourbon Villa at Daynabrook Farm-HOT TUB-1

Superhost

The exterior of a newly constructed villa is showcased, featuring a large front porch with wooden railings and two inviting chairs. The triangular roof design emphasizes the structure's height, complemented by a front door located centrally beneath an overhang.

4.88 out of 5 average rating, 78 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-6

A modern A-frame cabin is depicted, showcasing a welcoming porch with two wooden chairs. The structure features a dark exterior complemented by large windows and a distinctive peaked roof. The front door, painted in a soft orange hue, adds a pop of color to the facade.

4.9 out of 5 average rating, 93 reviews

Villa On the Bourbon Trail with HOT TUB-3