House vacation rentals in Original Highlands, Louisville

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Top-rated house rentals in Original Highlands, Louisville

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Top guest favorite

Home in New Albany

5 out of 5 average rating, 366 reviews

Welcome to the Bough House!

Listed on the National Registry of Historic Places, this beautifully renovated home offers vintage charm with modern amenities. Located just across the Ohio River from Louisville, only 6.6 miles from the Kentucky International Convention Center, 7 miles from the KFC YUM! Center, 12 miles from Churchill Downs, and one mile from shops and restaurants in historic downtown New Albany, IN, the Bough House is close to everything the Louisville region offers, with the peace of a quiet historic street.

Guest favorite

The exterior of a newly renovated river house is presented, featuring a large covered deck and a wraparound porch that offers views of the Ohio River. Lush greenery surrounds the property, enhancing its tranquil atmosphere.

Home in Elizabeth

4.86 out of 5 average rating, 183 reviews

Relaxing River House Retreat-Sleeps 10-12

Cozy newly renovated river house with ample entertainment space inside and out. Large covered deck with wrap around porch and a beautiful view of the Ohio River. 1 mile from Horseshoe Casino, just minutes from entertainment and amenities of downtown New Albany, IN and Louisville, KY. Less than 10 minutes from a local winery, 2 breweries, and Chariot Run Golf Course. Perfect for large groups or a romantic weekend getaway! Additional detached bonus bedroom. $100 extra per stay at guest's request.

Superhost

A charming single-story house features a light grey exterior with dark shutters framing the windows. A mint green front door serves as a focal point, while a wooden railing and low-maintenance landscaping enhance the welcoming entrance.

Home in Louisville

4.87 out of 5 average rating, 334 reviews

Designed for Families • Peaceful Neighborhood

Perfect for Families - We love hosting families! We have a little kids, so we know how nice it is to stay in a home with essentials for the littles. The kids’ room includes a pack 'n play, highchair, chalkboard wall, and a variety of books and toys. Enjoy family movie time with Disney+. Safe & Central Location – Situated in a quiet, centrally located neighborhood with easy access to top attractions, all within a 10-minute drive. We're Legally Registered - illegal listings may be shut down.

Top guest favorite

An open-concept living area features contemporary furnishings, including two lounging chairs and a couch. A sleek coffee table sits in the center, while a bright kitchen is visible in the background. Large windows frame scenic views of the water, filling the space with natural light.

Home in Louisville

4.95 out of 5 average rating, 171 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Guest favorite

A charming house features a classic facade with tall white columns and a wide staircase leading to the entrance. Large windows are framed with flowing curtains, allowing natural light to enhance the inviting atmosphere under the leafy canopy of surrounding trees.

Home in Louisville

4.87 out of 5 average rating, 172 reviews

Prime Highlands Location - 500ft fro. Midcity Mall

Formerly known as Breslin House, this well-loved Airbnb (126 five stars reviews) is under a new host. We are confident you'll love it as much as everyone did before! Our house is located on a quiet street, but steps away from restaurants, bars, boutiques, and cafes on Bardstown Rd. It's perfectly situated in the heart of the Highlands so you can walk to almost everywhere. Our home is very spacious with 3 large bedrooms, so you'll have plenty of privacy even with a large group.

Guest favorite

A spacious outdoor living area features a covered patio with comfortable seating and decorative plants. The area includes a ceiling fan and is bordered by wooden fencing, providing an inviting atmosphere for relaxation. A textured rug lies on the gravel surface.

Home in Louisville

4.96 out of 5 average rating, 224 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

Guest favorite

A living and dining area is presented with a glass dining table surrounded by four upholstered chairs. A comfortable blue sofa and decorative armchair provide seating options. A flat-screen television is mounted on the wall above a gas fireplace, with natural light filtering through the nearby windows.

Home in Highlands

4.92 out of 5 average rating, 214 reviews

Walk to All! 2 Kings, 2.5 baths, washer/dryer

3 story townhouse in city's best location. 1/2 block to great restaurants, cafes, shops and Cave Hill. Parking for 2 cars. Sleeps 8 in two king bedrooms and 2 sleeper sofas. 3 bathrooms (2 full and a 1/2) Wifi, gas fireplace, cable, lux linens, washer/dryer (with detergent/dryer sheets), fully equipped kitchen and more! Great local coffee just across street. Two of Louisville's best restaurants with 2 blocks. Half dozen fun nightspots within a 2 minute walk.

Guest favorite

A stylish living area is presented with a green, tufted sofa adorned with decorative pillows. A wooden coffee table sits in front, featuring a remote control and a magazine. The walls are decorated with a variety of framed artwork and hanging plants, enhancing the space's charm.

Home in New Albany

4.95 out of 5 average rating, 213 reviews

The Green House in Downtown

Newly renovated 1920s shotgun house in Downtown New albany. Perfect for those who want the convenience of being in the middle of it all, but still want an authentic and stylish oasis to relax in. Comes with all the amenities you would expect for a convenient stay including fully equipped kitchen, private back yard, off street parking, and self check-in. Walk or Bike your way to many local restaurants, shops, or take the byway to enjoy the scenic Ohio River.

Guest favorite

The home's welcoming facade features a covered front porch with seating arrangements. A set of stairs leads to the entrance, framed by decorative railings. Fresh landscaping, including small shrubs and mulch, enhances the outdoor space, while trees provide partial shade.

Home in Louisville

4.91 out of 5 average rating, 157 reviews

New Signature Highlands Home- steps away from…

Welcome to our new to AirBNB Highlands home. Recently redecorated and updated, this home is steps away from many incredible local restaurants, bars, and shops. Less then one mile to Cherokee Park. Less then five miles to Churchill Downs, NULU, and the airport. You simply can’t beat this location. Safe, family friendly neighborhood with swing-set in the back yard (high chair, pack and play, toys, and more available upon request).

Guest favorite

The exterior of a recently renovated shotgun-style house features a welcoming blue front door and a small porch with a black railing. Light gray brick accents are complemented by traditional white trim. Nearby trees provide natural shade in the front yard.

Home in Germantown

4.94 out of 5 average rating, 120 reviews

Spruced-Up Shotgun, Steps to Logan St Market

Recently renovated full 2 bed/2 bath house in historic Germantown. Guest will enjoy a full kitchen with all utensils and appliances provided. Living room has 55' TV with plenty seating and light. Each bedroom has double bed with linens, dressers, nightstand, and closet. Full bathroom connected to each bedroom with towels and toiletries. Front and back door uses coded Yale locks. Security cameras on front and back doors.

Guest favorite

A cozy living room is depicted, featuring a mix of seating options including a patterned chair, a dark upholstered chair, and a grey sofa. A round wooden coffee table occupies the center, while a softly lit lamp and wall art add warmth to the space.

Home in New Albany

4.95 out of 5 average rating, 147 reviews

king bed and oasis backyard with hot tub

11 miles to Derby. Come enjoy our newly decorated house with a hot tub, gazebo outdoor fun area and lounge furniture and wood burning fire pit. The idea is to both indoor and outdoor give you a great experience that not everyone offers! We sleep 4 adults comfortably in our 1 KING size bedroom and 1 QUEEN size bedroom. We're located in a quiet neighborhood with a fully fenced in backyard and we're Pet Friendly with a fee!

Top guest favorite

A living room invites relaxation with vibrant green chairs paired with a plush blue sofa. A decorative coffee table sits on an ornate area rug, while a chandelier hangs from a deep blue ceiling above. Bright natural light is allowed to enter through the door framing.

Home in East Market District

5 out of 5 average rating, 140 reviews

Walkable+5 King Beds+Firepit+Bourbon Trail

Welcome to Washington Landing! From here, you will be perfectly poised to enjoy all the shops, breweries, restaurants, distilleries, waterfront concerts and the professional soccer stadium all within WALKING DISTANCE of this newly remodeled 4 bed/2 bath historic home. You would be hard pressed to find a better location! No locals No Parties - only registered guests