Holiday houses in Jefferson County

4.99 out of 5 average rating, 107 reviews

An inviting outdoor space features a spacious in-ground pool surrounded by a decorative fence. Lush green trees provide shade, while the backdrop showcases a sunset sky with soft purple hues. Comfortable lounge chairs are positioned near the water, enhancing the area's relaxing ambiance.

Home in Mount Washington

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

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The front entrance is showcased with a vibrant orange door framed by a decorative glass panel. The wooden steps are complemented by stylish railings, surrounded by green leaves and landscaping. The inviting entry indicates easy access to the home.

4.91 out of 5 average rating, 493 reviews

The House with the Orange Door

Near Churchill Downs (7mins) UofL (5mins) downtown (10mins) Convention Center (10mins) Fairgrounds (4mins), and close to restaurants, bars and coffee shops. The home offers two bedrooms with queen beds and a pull-out couch in the living room. Enjoy coffee or a relaxing evening on the back deck. The kitchen is fully equipped and the open living space provides a great area for socializing. Locally made art and decor is on display, adding to the uniqueness of the space. No local bookings please!

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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, 262 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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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, 258 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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A single-story brick home is featured, surrounded by well-maintained landscaping. A paved driveway leads to a two-car garage, and a basketball hoop is positioned on the right. The yard offers a grassy area with neatly trimmed bushes and trees providing light shade.

4.89 out of 5 average rating, 225 reviews

Lilly's Pad

Relax and unwind in between all your Louisville activities. We are close (4.4miles) from SDF airport ,and I65 and the Gene Snyder Freeway are less than 8miles away. There are a plethora of activities from shopping to entertainment venues such as horse racing at historic Churchill Downs, Louisville Zoo, Kentucky Kingdom amusement park, Muhammad Ali museum and childhood home, Louisville Slugger Museum, Valhalla golf club, and 36 Bourbon Distilleries as well as cave exploring and fishing.

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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 fenced backyard features a circular stone fire pit surrounded by four Adirondack chairs. A hammock hangs invitingly between two trees, with string lights softly illuminating the area. The lush grass complements the warm ambiance created as the sun sets in the background.

4.96 out of 5 average rating, 189 reviews

Lumos Stays: 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 (~317mbps), 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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4.96 out of 5 average rating, 49 reviews

Derby City Luxury Home! Spacious! Location!

Your Louisville respite awaits! Whether you're seeking accommodations for Derby weekend, sipping the Bourbon Trail, or simply visiting our beloved city - look no further. Stay in this fully renovated, yet historic, home within a short distance from Churchill Downs, the Kentucky Exposition Center, Downtown, and all of the local favorites. This 4-bed-2-bath home is equipped with a fully stocked kitchen, coffee bar, and entertainment center. We hope you enjoy your stay. Cheers!

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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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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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A comfortable living area features a light grey sofa and two matching armchairs, arranged around a circular coffee table on a textured area rug. A ceiling fan hangs above, and natural light filters through the large window, illuminating black and white framed photographs on the walls.