Family-friendly vacation rentals in Shelby County

4.95 out of 5 average rating, 291 reviews

Apartment in Louisville

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

4.96 out of 5 average rating, 271 reviews

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

4.97 out of 5 average rating, 334 reviews

Cabin in Henryville

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

4.93 out of 5 average rating, 255 reviews

Home in Harrodsburg

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

4.95 out of 5 average rating, 171 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

4.99 out of 5 average rating, 250 reviews

St. Matthews Haven - Near State Fair Fun, Hot Tub

* 3 Bedrooms, 5 Beds, 2 Living Rooms. * 2 1/2 Baths * 2,500 sq ft (235sqm) * Private patio * (2) 60” Smart TV's w/Bluetooth speaker * Attached garage * Fully equipped Kitchen, upgraded appliances & sink * Flat screen TV in each bedroom & cable * Safe neighborhood * Close to local spots shopping malls in Louisville, gym, and St. Matthews *Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required*

4.94 out of 5 average rating, 143 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

4.99 out of 5 average rating, 140 reviews

Farm stay in Pendleton

Fossil Creek Woodlands...Rustic, Private, Retreat

Fossil Creek provides a rustic relaxing environment for family and friends to escape the hustle and bustle of every day life and enjoy beautiful Kentucky woodlands. Our home is situated at the base of 65 wooded acres in Oldham County Kentucky. Its name comes from the plethora of fossils that can be seen in the creek that runs along the front of the property. Our place is great for couples, families, reunions, retreats and church groups.

Apartment in Mount Washington

4.95 out of 5 average rating, 204 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

4.98 out of 5 average rating, 337 reviews

Farm stay in Goshen

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

4.99 out of 5 average rating, 135 reviews

Loft in Shelbyville

Urban Loft Sleeps 16 and close to Buffalo Trace

"The biggest and best rental option in downtown Shelbyville, Urban Loft is the best place to stay in town. It’s an absolutely breathtaking space with enough sleeping space for well over a dozen guests to comfortably cohabitate, but the space is so absolutely picture perfect and secluded that you might have trouble coaxing all your traveling companions to ever leave." - Bourbon Review Magazine