Family-friendly holiday rentals in Jefferson County

A spacious living area features a comfortable sectional sofa and a large, cozy bean bag styled cushion. Decorative lighting provides a warm glow, and a stone fireplace is centered on a light blue wall. A patterned area rug adds color, while large windows invite natural light.

4.99 out of 5 average rating, 169 reviews

Cozy cottage open for Bourbon and beyond

This secluded mid century cottage is just minutes to downtown and other amenities. Located in Clifton Heights, this three bedroom, bath and a half home is inviting and cozy. Located 6 miles from two large malls, 1 mile from the new walking bridge over the Ohio River, and one and a half miles to unique shopping, nightlife and restaurants. Also, the home is only a short distance to I 71 and I 64. This makes everything convenient and accessible from this private location. The home has vintage charm with renovations for convenience. Each Bedroom has a flatscreen TV as well as a 56 inch flatscreen in the living room. There is a private front yard with gardens, seating, and a grill. There are 6-7 spaces for off street parking. The eat-in kitchen seats six, with a double oven microwave, full-size fridge, gas stove and a dishwasher. There is service for 12 including Louisville Hadley Pottery.

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A spacious living area features a comfortable gray sectional sofa, accented by decorative pillows. A round coffee table sits at the center on a striped rug. Tall windows allow natural light to fill the room, while a brick fireplace adds warmth, complemented by wall decor.

4.95 out of 5 average rating, 102 reviews

Spacious 4 BD Home | 5 min to Airport • 6 min Expo

Your Louisville home base! Nestled in the highly desirable Upper Highlands this stylish retreat offers convenience, comfort, and charm for families, business travelers, events, and weekend explorers.Whether you're here for the Kentucky Expo, flight at SDF, downtown adventure, or a fam getaway Prime Location: 5 minutes from Louisville Muhammad Ali International Airport Around 6 min to the Kentucky Exposition Center & Freedom Hall Easy drive to downtown’s Bourbon District, Yum! Center, and more

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A modern kitchen space features white cabinetry and open shelving, displaying neatly arranged dishes and plants. A breakfast bar with four metal stools offers a casual dining area, complemented by a window that allows natural light to brighten the room.

4.97 out of 5 average rating, 263 reviews

502 House @ Progress Park w/ Game Room

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The 502 house combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

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4.98 out of 5 average rating, 320 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

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A cozy living space features a brown sectional sofa adorned with a cushion displaying the phrase 'CALL ME OLD FASHIONED.' Green plants are positioned beside the couch, while patterned wall art and a decorative sign contribute to the inviting decor.

4.99 out of 5 average rating, 259 reviews

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!

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The exterior view of the red-themed house is shown, emphasizing the sloped roof and welcoming front porch. A spacious deck features seating options and a grill. Lush greenery surrounds the area, contributing to a peaceful outdoor environment.

4.99 out of 5 average rating, 124 reviews

Colonial Hideout | Close to fairgrounds!

Ready for a relaxing stay in Louisville, Kentucky?! Welcome to a wonderfully homey stay minutes away from the KY Expo Center & Kentucky Fair Grounds. Perfect for hitting the Kentucky Bourbon Trail, heading to one of Louisville's many events, or heading to a game at the KFC Yum! Center. The property & driveway can easily manage horse trailers and car trailers if you’ve got a lot to haul. We look forward to hosting you! Family Ready: Pack n Play, High Chair, Plastic Plates & Cups

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A bright living room features a dark tufted sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, and a large flat-screen TV is mounted above a white mantel. Two armchairs are positioned near a window, with natural light flowing into the space.

4.94 out of 5 average rating, 463 reviews

DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT

- 3 min drive to U of Louisville - 5 min drive to KY Expo Center - 7 min drive to Louisville Zoo This gorgeous 3-bed, 2-bath house is less than 4 miles from downtown Louisville. With its fully-equipped kitchen, spacious rooms & completely renovated kitchen, the house is the perfect base for large groups wanting to explore the city. Enjoy the wide variety of shops, restaurants, & bars nearby. Kentucky Derby fans love the close proximity to Churchill Downs. No Locals Please

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The living area features a comfortable dark gray couch, an accent coffee table with a vintage trunk design, and two bright orange chairs. Natural light filters through large windows, accentuated by soft blue curtains. A colorful area rug adds warmth, with decorative wall art enhancing the space.

4.9 out of 5 average rating, 178 reviews

The Jungalow: 65" 4K TV, memory foam, kid-friendly

Michael and Ashley (Lumos Stays) welcome you to Louisville, home of bourbon! Centrally located, minutes from the interstate, and close to downtown and the bourbon trail, this is your home base for adventure. Enjoy the 65" 4K Roku TV, fast wifi (~387mbps), green tea memory foam mattresses, modern kitchen, kid-friendly amenities… and did you see that outdoor space? Solo Stove fire pit, hammock, propane grill, and games. Enjoy the private fenced-in backyard and large driveway!

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Superhost

The exterior showcases a historic building with large windows allowing natural light. A welcoming entrance leads to additional outdoor seating. An indoor game area features a shuffleboard table and playful décor. A cozy outdoor space is highlighted by a fire pit, surrounded by modern seating.

4.92 out of 5 average rating, 298 reviews

Best Location in the City-2 Story Patio & Hot Tub

The Saddle Inn has everything you need for your upcoming stay. Situated in the heart of the city and walking distance to the best restaurants and bars in town, you are booking convenience when you book our home. This house has vintage Kentucky flare with modern furnishings & updates. It boasts 3 bedrooms, a 2 story patio, hot tub, fire pit, ping-pong table, shuffleboard, and all the bourbon barrels one can hope for in Kentucky. There's no better location than this one.

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4.98 out of 5 average rating, 263 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

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4.99 out of 5 average rating, 137 reviews

Cottage in Prospect

Cozy Cottage on Famous Kentucky Farm

Curl up by a wood-burning fireplace in a charming 2-bedroom cottage on Foxhollow Farm - Kentucky's most beloved farm stay, featured on Bravo's Top Chef. Perfect holiday escape: 1,300 rolling acres, horse views from the porch, private nature trail, and Thanksgiving/Christmas/New Year's availability. Just 20 min from Louisville's holiday events, bourbon trail, and Churchill Downs. Book your winter retreat now, holiday weekends fill fast!

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