Holiday rentals with outdoor seating in Jefferson County

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

River City Loft - Free downtown parking!

If this loft is booked, please check out my other listings.. www.airbnb.com/h/derby-city-loft www.airbnb.com/h/river-city-loft www.airbnb.com/h/falls-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! Located 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

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.

Bourbon Trail Spacious Backyard NEW HotTub Grill!

The Burnt Barrel – Your vibrant Louisville getaway in the historic Shelby Park neighborhood! Perfect for couples, business travelers, or event visitors. Enjoy high-speed Wi-Fi, a dedicated workspace, fully equipped kitchen, & a NEW hot tub & grill. Just minutes from Whiskey Row, the Urban Bourbon Trail, Churchill Downs, NuLu, UofL Health, and the Convention Center. Explore iconic spots like Old Forester, Angel's Envy, & Evan Williams — all within 10–15 minutes. True Louisville charm awaits!

The Writer’s Den

Take it easy at this unique and tranquil cabin getaway. Nestled on a wooded hillside overlooking the Louisville skyline, The Writer’s Den is a great place to call home. Located just off interstate 64 and 10 minutes from downtown Louisville, the cabin gives peaceful seclusion and location convenience for those looking to explore the area. With a screened in porch, back deck lounge, loft space and all the comfort amenities, you’ll be on your way to writing the next great novel!

An Unhurried Stay in Butchertown · Steps from NuLu

Some places just make you feel held. This is one of them. A Jaclyn Journey Hospitality stay - set inside a 19th-century building on the edge of Louisville's Butchertown & NuLu neighborhoods. This apartment has been designed with the kind of care that's hard to put your finger on but impossible to miss. Every detail - from the original fireplaces to the lime-washed bedroom walls - has been chosen to make you feel genuinely at ease, not just comfortable.

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

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.

Stay in Historic Butchertown, Blocks From NuLu

With its prime location at 1025 E Main St at the intersection of Louisville's Butchertown and NuLu neighborhoods, you'll be blocks away from the city's most vibrant and exciting districts. With this beautifully renovated, designer-curated home as your base, walk to the area's trendiest shops and restaurants, sample local craft beers at one of the nearby breweries, or enjoy tastings on one of the many bourbon tours that the city is famous for.

Luxury 1BR Apt w King Bed near Louisville KY

Stylish 1BR apartment in the heart of Downtown New Albany Indiana. This apartment is centrally located to great shops and fantastic dining in downtown New Albany all within walking distance, 10 minutes to Downtown Louisville and the KFC Yum Center, and a short drive to Caesar's Casino. With a beautiful view of the downtown area from the living room, this apartment comes fully stocked with every amenity for your short or long-term stay.

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.