Holiday 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, 250 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.

4.98 out of 5 average rating, 147 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.

4.98 out of 5 average rating, 304 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 image captures a cozy living area featuring two glasses of wine on a coffee table. A four-poster bed with white sheer curtains is visible in the background, creating a charming focal point. Bookshelves line the wall, adding a touch of warmth and character to the space.

4.9 out of 5 average rating, 682 reviews

Limerick Carriage Company

The Carriage House is ready for you and some-bunny special! Our Carriage House is warm and inviting to guests from all over. We are located close to downtown, Central Park, UofL, & the Bardstown Road corridor. There are many unique shops, restaurants, bars, & places to visit close by - some are walkable in warmer weather. The Carriage House has undergone a complete renovation - we hope you love it as much as we do! Don’t let the outside fool you - the inside of our home is the treasure!

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.

4.9 out of 5 average rating, 335 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.

4.94 out of 5 average rating, 119 reviews

A cozy living area features wooden walls and a stone fireplace, creating a rustic ambiance. Comfortable seating includes a couch and two armchairs, with a coffee table placed centrally. Natural light enters through a window, highlighting decorative elements and a soft area rug on the floor.

Cabin in New Albany

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!

4.92 out of 5 average rating, 123 reviews

A spacious and uniquely decorated studio features hardwood floors and warm yellow walls. A cozy bed is positioned against a wall adorned with artwork, while a vintage wardrobe and eclectic furniture pieces add character to the space. Natural light filters in from a nearby window.

Flat in Louisville

Heart of the Highlands- Derby Weekend available.

The whole group will be comfortable in the spacious and unique space. You will be staying in a working photography studio. Decorated with eclectic furniture, hardwood floors and beautiful photographs. The studio offers a full kitchen, spacious living area, deck and shared fenced backyard. The Highlands is charming neighborhood with wonderful restaurants and shops. I love the atmosphere in my neighborhood, you will find vintage clothes, vinyl records, and local breweries.

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 out of 5 average rating, 140 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.

Guest suite in Louisville

The inviting bedroom features a spacious bed with white linens and a soft green throw. A mounted projector is positioned on the ceiling, with greenery-patterned wallpaper creating a serene ambiance. Two bedside tables with lamps and a bench at the foot of the bed enhance functionality.

4.99 out of 5 average rating, 228 reviews

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.

4.98 out of 5 average rating, 249 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.

An open concept living area is displayed, featuring a large comfortable sofa complemented by an area rug. Exposed brick is visible on an interior pillar, while a television hangs on the wall opposite. Floor-to-ceiling windows allow natural light to fill the space.

4.88 out of 5 average rating, 134 reviews

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.