Vacation rentals with outdoor seating in Jefferson County

Guest suite in Jeffersonville

An outdoor fire pit is surrounded by several wooden chairs, providing a gathering space for relaxation. The calm waters of the Ohio River reflect the night sky, with soft lights from boats creating a serene atmosphere. Low greenery and gentle clouds frame the scene.

4.95 out of 5 average rating, 236 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Superhost

4.9 out of 5 average rating, 138 reviews

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!

4.99 out of 5 average rating, 107 reviews

A welcoming exterior view of a stylish house features a covered front porch with seating and decorative elements. The spacious interior showcases a cozy living area with comfortable seating and art on the walls. A well-maintained outdoor space includes a putting green. Natural light brightens the rooms.

Home in Jeffersonville

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.

4.95 out of 5 average rating, 351 reviews

A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.

Cabin in Louisville

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.

A modern kitchen is showcased, featuring sleek cabinetry and an island with seating for four. Three pendant lights hang above, providing warm illumination. The stainless steel appliances include a refrigerator and a microwave. Natural light enters through large windows, adding brightness to the space.

4.91 out of 5 average rating, 199 reviews

Private Parking in GTownWalk to Coffee,Shops,Bars!

Shotgun Rye is ready to host your stay in Louisville! Located close to everything cool in Germantown and Highlands area! People visit for Bourbon Tours, Ky Derby, Conventions, Expo Ctr, UL graduations and sporting events, live music and so much more! Completely remodeled with all the modern conveniences & a comfortable, casual touch. But with so much to see and do in Louisville you’ll load up your itinerary with unforgettable experiences. Great location walk to bars, restaurants and shopping!

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, 210 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!!

4.98 out of 5 average rating, 256 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.

The exterior of a charming single-story house is shown, featuring a covered porch and stone columns. Lush green bushes frame the entrance, and two seats are visible on the porch. A modest yard surrounds the house, with a clear sky above.

4.91 out of 5 average rating, 296 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

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, 409 reviews

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.

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.

4.96 out of 5 average rating, 243 reviews

502 House @ Progress Park w/ Game Room

Welcome to Progress Park! A true getaway for fun! Located on a 12 acre Airstream Glamping resort w/ a 2 acre swimming pond. Sleeps 8 comfortably in the beds with 2 leather futons. Enjoy all the luxuries of home w/ added amenities such as a custom game room & luxurious backyard with TV, firepit & grill. Relax, unplug and reconnect in our little slice of heaven. Progress Park has 8 total units on site. 2 houses, 5 airstreams & a bunk house. *DERBY IS A MIN THURS-SUN REQUIRED

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.

4.95 out of 5 average rating, 159 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!

The kitchen features a warm wood countertop complemented by white cabinets and shelves. A stainless steel sink and dishwasher are visible, along with a Keurig coffee maker. Natural light filters through the window, illuminating neatly arranged dishes and kitchen supplies.