Holiday rentals with outdoor seating in Louisville

Bourbon Trail Spacious Backyard NEW HotTub Grill!

The Burnt Barrel, discover your vibrant Louisville getaway! Perfect for couples, business travelers, or event visitors, this cozy home offers high-speed Wi-Fi and a dedicated workspace, fully equipped kitchen, and a NEW hot tub and grill for you to enjoy! Guests rave about its comfort, walkable location, and modern amenities. Enjoy nearby bars and restaurants all just minutes from downtown, UofL Health, and the Convention Center. Experience true Louisville charm and convenience! Book a stay now!

2 br home, walking distance to much entertainment

Home located in the historic Irish Hill neighborhood, just a short walk to popular Baxter Ave and Bardstown Rd, famous for its restaurants, coffee shops and nightlife. Downtown and Nulu are a very short drive away, many great bars and distilleries are walking distance. Home built in 1879, entirely renovated with a modern kitchen, fully fenced backyard, private parking and fire pit.Master bedroom has a king size bed and it’s own bathroom with jetted tub. We look forward to your visit, thank you!

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.

The House with the Orange Door

Located near Churchill Downs, UofL, downtown, the Convention Center and Fairgrounds, and a short distance to restaurants, bars and coffee shops. This single family home offers two bedrooms with queen beds and a pull-out couch in the living room. Enjoy coffee or a relaxing evening cocktail 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.

4th Street Suites - Beautiful King Bed Suite

Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

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.

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

Charming Penthouse/Rooftop Patio/Downtown

Unwind and enjoy sweeping river views on the rooftop patio while staying in this private 5th floor Penthouse apartment. Intentionally designed and decorated. Features include: a full upscale kitchen, open concept living and dining area, cozy King bed, large plush bathroom, and laundry in the suite. Whether visiting for work or pleasure, this spacious urban suite is located on The Bourbon Trail and within walking distance to Louisville's most popular venues!

Historic Derby Carriage House

Historic Carriage House- 2 BR, 1.5 BA Oasis situated 10 mins to downtown, a 10 min walk to restaurants, shops, and groceries, and a 15 min drive to Churchill Downs. Right across the street from two parks and bike trails for a pleasant escape close to the bustle of Louisville nightlife. Free Parking, Wifi and Smart TV access accommodation as well as spa bathroom with soaking tub, jetted shower, and heated towel rack. Down the street from Cherokee Art Festival.

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.