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.

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!

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 space designed for comfort, beauty, and ease. 🌟 Peaceful, central, and truly one of a kind—your perfect Indy stay begins here

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.

National historical home in the Heart of Lexington

Timeless Elegance in the Heart of Lexington Stunning 5bdrm, 3ba historical home located in downtown Lexington, Ky. Perfect for large groups, families, or friends looking for a memorable stay in this luxurious property combines charming historical details with modern amenities for the ultimate getaway. Just steps away from the iconic Rupp Arena. Whether you're attending an event, enjoying a day at Keeneland, or exploring distilleries, you’ll be in the ideal spot for it all. Listing ID15068130-1

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! 🌅

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!

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.

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!

Zestlife-HeatedPool-LuxeEscp-ThemedRooms-GameRoom

Experience an ultimate luxurious retreat in Indianapolis boasting unique and stylish decor with a refreshing touch of lemon zest and beach vibes! Delightful Disney-inspired themed spaces, a one-of-a-kind theatre room, a spacious backyard oasis with a Heated Pool, Spa, and modern resort amenities will charm guests of all ages. It's truly everything you could want for an unforgettable magical vacation! ✔ 25min Indy downtown, 15min Geist Reservoir, 35min Airport ✔ Safe & upscale location

Suburban paradise in Liberty TWP

Relax in total comfort with your family, and let your group enjoy a nice private backyard oasis with a deck and pool. This property has a crystal clear pool, furnished deck, furnished patio, newly renovated interior, fully equipped laundry, and more. A blend of comfort, style, and convenience greets you as soon as you enter our newly built open-concept home. While decorating this inviting retreat, we have worked hard to create a home away from home feeling for you and your guests.