Family-friendly vacation rentals in Shepherdsville

4.94 out of 5 average rating, 289 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.

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Home in Brandenburg

4.94 out of 5 average rating, 273 reviews

Luxury lakehouse retreat with picturesque views

Recently renovated lake house with rustic contemporary decor. Gourmet kitchen includes dishes, cookware and small appliances as well as a deluxe espresso/cappuccino maker. House is located in a gated, private community with a 320 acre lake up to 70 ft deep. Only pontoon boats and fishing boats permitted, ensuring a quiet lake experience and wake-free dock sitting. Two kayaks, canoe, paddle board and some basic fishing equipment for guest use. Pontoon rental by owner - separate contract.

4.87 out of 5 average rating, 351 reviews

☆ .9 Miles to Expo Center ☆ Large Backyard

• Central Location - 0.9 miles to KY Expo Center - 15 min drive to downtown (great access to the interstate) - Churchhill downs = 4.0 mi - University of Louisville = 3.1 mi - Kentucky Kingdom = 2.2 mi - Downtown Bourbon Distilleries - 5mi • Fenced-in backyard (1/2 acre) with gas grill and shaded deck • Secured parking for 4-5 cars • Fully equipped + stocked kitchen • Quiet & safe neighborhood • High-speed internet (100mbps) + Netflix included • Onsite washer + dryer No locals, please

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!

4.98 out of 5 average rating, 135 reviews

Home in Elizabeth

Cabin on Lake Close to Louisville Ky

Welcome to Little Cedar Lodge, our little slice of heaven near the town of Elizabeth, Indiana. Enjoy the peace and solitude overlooking the quiet private lake (wake speed only), yet close to Caesar’s Casino, golf, wineries, and the city of Louisville with all its activities and nightlife. Great for a romantic getaway for two, or for your entire family. It would also be great for a small church or business retreat. We can accommodate up to 10 if you double up in some beds.

4.99 out of 5 average rating, 250 reviews

NEW Hot Tub, Walk 2 Park, Whole Foods, Movies Mall

* 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*

4.93 out of 5 average rating, 229 reviews

Cabin in Springfield

Cozy Cabin on the Bourbon Trail

Our place is close to the Bourbon Trail. You’ll love our cabin because of the warm interior and amazing outdoor space. Our place is good for couples, solo adventurers, business travelers, and families. This cabin located in the country on our 100 acre farm, but you are 3 miles from restaurants, groceries, pharmacies and shops. The location is also central to the distilleries: 15mi to Maker's Mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington, and Louisville

4.96 out of 5 average rating, 304 reviews

Apartment in Louisville

Seneca View

Open, airy space with modern amenities. Plz, NO smoking, toking , vaping, or any drug use in/on property-- $300 fine. Convenient location in a quiet, sought-after neighborhood, yet within a few minutes of a bustling, busy Bardstown Road with lots of places to eat, shop and browse. Easy access from all major interstates: I-71, I-65 and I-64. Come stay for a week on business (work desk is set up) or use for a fun, getaway weekend.

4.96 out of 5 average rating, 126 reviews

Derby City Oasis

Welcome to your cozy getaway in Louisville! This charming Cape Cod home in the Beechmont neighborhood is just 1.5 miles from Churchill Downs and 2 minutes from the airport. With 3 bedrooms, 2 full baths, and a full-size futon, it’s perfect for families or small groups. Essentials like gas, groceries, and liquor stores are right around the corner. Enjoy a relaxing stay in this inviting home—your perfect base for exploring the city!

4.95 out of 5 average rating, 171 reviews

Cottage in Louisville

2 BD 1 BA Serene Setting Retreat House

Carriage home is located on beautiful Arnoldtown Rd. 15 min. from Churchill Downs and 20 min. from downtown Lou. We are 15 minutes from Freedom Hall or the Fairgrounds and 22 miles from Fort Knox. It sits in a natural setting on 5 beautifully landscaped acres. There is a large parking area for those who may need to bring a trailer. Bathroom and bedrooms are on the 2nd floor. Peaceful..in a rural setting but inside the city.

Apartment in Mount Washington

4.95 out of 5 average rating, 203 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.