House vacation rentals in Shelby County

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Top-rated house rentals in Shelby County

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Top guest favorite

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

Home in Lawrenceburg

4.98 out of 5 average rating, 133 reviews

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Superhost

Home in Finchville

4.91 out of 5 average rating, 114 reviews

Thoroughbred Horse Farm Cabin-located on Lamb Lake

Beautiful cabin located on a working horse farm just miles from Louisville, Frankfort and Lexington! Take in the farm scenery from our porch bed swing, or large patio with fire pit. Play a round of Air hockey, foosball, basketball shootout, corn hole, or bucket golf during your stay! Several Bourbon Distilleries are within a 30 minute drive of the property. The Cabin is 4 miles from the Outlet Shoppes of the Bluegrass, 15 miles from Taylorsville Lake, and 13 miles from Valhalla Golf Course.

Top guest favorite

The exterior of the home presents a charming facade with white siding and brown shutters framing two windows. A green door welcomes guests, flanked by small evergreen shrubs. Stone steps lead to the entrance, surrounded by seasonal foliage.

Home in Shelbyville

5 out of 5 average rating, 8 reviews

WillHelpFloodVictims | DerbyDiscount | WelcomeTreat

Cozy 750 sqft home designed for convenience and comfort 1 bdrm w/ comfy queen bed, 1 bath and a pull out couch Stocked w/ snacks, toiletries, and coffee & tea options Outside enjoy the fire pit (wood provided) or fire up the grill for a burgers or steak Located across from the fairgrounds in safe, charming downtown Shelbyville, you'll have easy access to local events, dining, and shopping Whether you're here to explore the Bourbon Trail or just unwind this spot offers everything

Top guest favorite

The exterior of a charming house features a red front door framed by large windows. A wooden deck with railings leads to the entrance, complemented by surrounding greenery and decorative elements. A pathway invites guests to explore further, with a glimpse of the lake visible nearby.

Home in Shelbyville

5 out of 5 average rating, 24 reviews

Bourbon by the Lake

Peaceful, Beautiful 4 bedroom, 2 bathroom house sitting on Guist Creek Lake in Shelbyville, KY located very close to the Bulleit Bourbon Distillery. Lake view from two of the four bedrooms. Perfect for bird watching. Guist Creek Lake is a great kayaking and fishing lake. Patio off the main living room with patio table and chairs. Two comfortable living room spaces with smart TVs, games, and books. Beautiful sunroom overlooking the lake. Nice patio space. Lake access with boat dock.

Top guest favorite

The farmhouse features a welcoming front porch shaded by large trees. A spacious hot tub is visible on the back deck, and a game table for poker is set up in the hangout room. Yard games are arranged outside, inviting leisure and enjoyment.

Home in Bagdad

4.95 out of 5 average rating, 40 reviews

Stylish House Near Lou Lex | Hot Tub | Games

Nestled in the heart of Kentucky’s Bourbon Trail, our spacious farmhouse is the perfect sanctuary for large groups to relax. Enjoy stunning sunrises from the front porch, soak in the hot tub, and make memories in the game room. Conveniently located just a short drive from the Bourbon Trail, this home sits in the serene countryside between Louisville and Lexington, offering the perfect blend of convenience and Southern charm. Book For Lasting Memories Bagdad—See Details Below!

Top guest favorite

A charming brick home is set against a backdrop of lush greenery and open fields. The house features a welcoming front porch with seating and a large lawn that provides ample outdoor space for relaxation. Clear skies above enhance the rural setting.

Home in Pleasureville

5 out of 5 average rating, 97 reviews

Pleasureville - The name says it ALL

This location is a Pleasure! Cozy Kentucky home off the beaten path, but close to attractions. Imagine after a full day on the bourbon trail enjoying your own piece of Kentucky with a drink in your hand. Access to 25+ acres of beautiful farmland and super clean, fully stocked private home. Close to the Outlet Shoppes of the Bluegrass making it a perfect ladies weekend get away. Additional meeting/event space available in the renovated on site barn. Reminder No Pets allowed.

Top guest favorite

The historic home is depicted in a serene landscape, featuring a combination of warm colors. A welcoming porch stretches across the front, complemented by multiple windows and a distinctive roofline. Lush greenery surrounds the property, enhancing its inviting presence.

Home in Crestwood

4.96 out of 5 average rating, 24 reviews

The Yellow House @ Floydsburg

This Historic Home sits on 2.5 acres of a gorgeous park like setting in a convenient location! Your travel group will be comfortable in this spacious and unique property. Perfect for family vacations or guests coming in town for weddings as this property is close to many different wedding venues in the area, including Duncan Memorial Chapel, Bradshaw Duncan House, & Yew Dell Gardens, and only 25 minutes to downtown Louisville. Come relax & enjoy your Home Away from Home!

Guest favorite

The exterior of a two-story colonial home is displayed, featuring a red brick facade, white columns, and green shutters. A spacious lawn surrounds the house, complemented by well-maintained landscaping, with a screened porch visible on the right side and a tree to the left.

Home in Shelbyville

4.94 out of 5 average rating, 66 reviews

B on the Bourbon Trail with pub, pool and hot tub

Discover Kentucky's Finest - B on the Bourbon Trail. With a saltwater pool, hot tub, fire pit, and Pub B, this historic colonial estate on 3 acres is near over 30 renowned distilleries, 35 minutes from the iconic Churchill Downs, and just an hour away from the prestigious Keeneland racecourse, B On The Bourbon Trail offers unparalleled access to Kentucky's most treasured attractions and promises an unforgettable experience in the heart of Kentucky's bourbon country.

Guest favorite

An outdoor seating area features cushioned furniture arranged around a central fire pit. Soft string lights are visible above, creating a warm ambiance. Surrounding trees provide a lush backdrop, while a patterned rug adds a cozy touch to the deck.

Home in Bagdad

4.97 out of 5 average rating, 34 reviews

SALE! *Pet-Friendly * LUX Hot Tub

🥃TRAILSIDE COUNTRY HAVEN🥃 in Bagdad, KY. ★★★★★ · 3 BR · 5 Beds · 2.5 Baths Welcome to TRAILSIDE COUNTRY HAVEN, A BEAUTIFUL HOME professionally managed by Excellent Vacay Stays. This home is nestled IN THE HEART OF the countryside along THE BOURBON TRAIL in Shelby County. As your host, Iris, I'm excited to share this picturesque haven that offers a serene and private wooded area. Discover why our guests love the multiple decks and patios for outdoor enjoyment!

Superhost

A modern living area features a green sectional sofa arranged around a circular coffee table on a patterned rug. Large windows allow natural light to fill the space, while a decorative shelf with various items adds to the room's aesthetic. A potted plant complements the seating area.

Home in Shelbyville

4.81 out of 5 average rating, 32 reviews

Quiet Downtown Maple Cottage Gem

Welcome to our charming Maple Cottage in the heart of a peaceful downtown neighborhood. This 3-bedroom, 1-bathroom home has undergone a complete remodel, ensuring a cozy and comfortable stay in Shelbyville. Whether you're here for a weekend getaway or an extended stay, this cottage offers all the amenities you need. The fully fenced backyard offers privacy and space for relaxation and smores over the fire pit. Your Shelbyville adventure begins here!

Superhost

A graciously restored house features a distinctive green exterior with white trim and a covered porch. Columns support the balcony above, while the entryway is framed by a symmetrical arrangement of windows. Lush greenery surrounds the entrance, enhancing the inviting appearance.

Home in Shelbyville

4.79 out of 5 average rating, 107 reviews

2 Bed/2.5 Bath Restored Beauty - Pistachio Palace

Built 1904 and recently lovingly restored. Just 2 blocks off historical Main Street in Shelbyville with great antique and coffee shops, as well as some favorite pubs and restaurants. In the middle of the Bourbon trail and Horse country, short drive to the new Convention Center and the Outlet Mall. This neighborhood is in the midst of gentrification. 2 Queen Beds, one Roll-away, pack-n-play & high chair. Absolutely no pets, including service dogs.

Guest favorite

A spacious living area features two light-colored sofas arranged around a wooden coffee table, complemented by a large area rug. A ceiling fan provides comfort, while the open layout connects seamlessly to the kitchen, which is visible in the background.

Home in Louisville

4.88 out of 5 average rating, 8 reviews

Charming Louisville Home Perfect for Derby

Charming Louisville Home Perfect for Derby, minutes from Valhalla Golf Club and the Bourbon Trail Welcome to your home away from home! This is our personal house nestled in the serene neighborhood of Persimmon Ridge, this exclusive home is a perfect retreat for people in town for Derby, golf enthusiasts, bourbon trail adventurers, or anyone seeking a peaceful getaway. Just minutes from Valhalla Golf Club and the Bourbon Trail.