Holiday houses in Jefferson County

4.99 out of 5 average rating, 104 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!

The open living area showcases hardwood floors and features natural light from large windows. A leather couch is positioned beside a wooden coffee table. The modern kitchen includes a spacious island with bar seating for six, complemented by white cabinetry and stainless steel appliances.

4.98 out of 5 average rating, 296 reviews

The Lakehouse at Progress Park in Derby City

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The Lake 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.

4.98 out of 5 average rating, 318 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.

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, 256 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!

5.0 out of 5 average rating, 89 reviews

A cozy living area features a comfortable seating arrangement with plush armchairs and a spacious sectional sofa. A modern coffee table sits at the center, while a large flat-screen TV is mounted on the wall opposite. Natural light filters through sheer curtains.

Home in Germantown

~Modern~Luxury 3BR~Walkable~Patio heater

Discover unparalleled comfort at our new 3-bedroom retreat, nestled in the vibrant Germantown neighborhood. This chic and tastefully designed space is ideal for families or groups of friends seeking a luxurious getaway. ~ Patio heater, outdoor seating with fire pit/grill ~ Fully equipped kitchen ~ Bar with cocktail shaker set and ice maker ~ Board games ~ 65” Smart ROKU TVs ~ Laundry near bedrooms ~ High chair/pack ‘n play with mattress/gates ~ Ring security system ~ Hi-speed WiFi

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, 122 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

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, 461 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

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, 296 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.

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.

5.0 out of 5 average rating, 146 reviews

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

4.98 out of 5 average rating, 259 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.

A large wooden dining table is centered in the room, surrounded by wooden chairs. Two framed vintage world maps hang on the walls, adding an earthy tone to the space. A simple vase with greenery sits atop the table, enhancing the natural decor.

4.98 out of 5 average rating, 210 reviews

"The Brook" - Louisville

Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!