House vacation rentals in Original Highlands, Louisville

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Top-rated house rentals in Original Highlands, Louisville

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Guest favorite

A modern living area features a plush gray sofa and clear coffee table, complementing the warm wooden floor. Natural light enters through large windows, illuminating the space. Two white accent chairs are positioned nearby, while a sleek flat-screen television is mounted above a decorative fireplace.

Home in Germantown

4.95 out of 5 average rating, 171 reviews

Best for Bourbon Trail and Beyond!

NOTE SPECIAL CANCELLATION POLICY FOR DERBY AND BOURBON AND BEYOND BOOKINGS! Original charm with a modern twist. Reno'd 1900s shotgun home perched on the Kentucky Bourbon Trail. Enjoy a comfortable stay near Louisville's best spots in the historic Highlands/Germantown neighborhood. Notice that we have THREE full baths. Swan Haus is luxuriously spacious for 2, perfect for 4, and very comfortable for 6 guests who plan to be out and about enjoying the city. Swan Haus is the place to stay anytime!

Top guest favorite

A two-story building is framed by lush greenery and a well-maintained exterior. The ground-level white porch is furnished with bright red chairs, flanked by steps leading to the entrance. A welcoming pathway runs between manicured bushes and trees, enhancing the inviting façade.

Home in Original Highlands

4.98 out of 5 average rating, 102 reviews

Highlands Lookout-3BR 3.5BA-Walk to Tons +Parking

Welcome to Highlands Lookout, your ultimate spot for a good time on Bardstown Road in the lively Highlands of Louisville! 3 Huge bedrooms plus 3.5 Baths. Perfect for guys' or girls' weekends, concerts, and conventions. Immerse yourself in the vibrant atmosphere of "Keeping It Weird." Unwind on our balcony or mix up a cocktail at our wet bar. Close to distilleries, bars with rare bourbons, downtown, racetrack, and the airport. Your gateway to a thrilling Louisville adventure! Off street Parking!

Guest favorite

The kitchen features warm wooden cabinetry and modern appliances, including a black refrigerator and microwave. A central island provides additional prep space, complemented by metal stools. Natural light fills the room through the windows, enhancing the spacious layout, while a doorway leads to another area of the home.

Home in Original Highlands

4.94 out of 5 average rating, 225 reviews

Cheerful Highlands Home with Parking*Cherokee*NuLu

A Modern 1900s Bungalow in the Prime Location for a true Louisville experience. This 3bed/2bath home is thoughtfully & comfortably furnished to make your stay memorable. A gracious front porch & patio for relaxing. Walkable to nearby pubs and restaurants. Off street parking. A wonderful place to stay! 0.6miles to Paristown Pointe 4min to Angels Envy 7min to ConventionCenter 8min to YUM Center 14min to Louisville SDF Airport 14min to Kentucky Exposition Center 13min to Churchill Downs Track

Guest favorite

A spacious living area is presented, featuring a large flat-screen television mounted above a decorative fireplace. A sleek leather sofa and two green armchairs are arranged around a central coffee table. Light-colored walls and hardwood floors contribute to a bright and welcoming environment.

Home in Louisville

4.94 out of 5 average rating, 157 reviews

2 br home, walking distance to much entertainment

Home is 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 is a quick drive away, lots of bars and distilleries are walking distance. Home built in 1879, entirely renovated with a modern kitchen, fully fenced backyard, private parking and a lovely fire pit. You will have a master bedroom with a king size bed and your own bathroom with jetted tub, very relaxing. Thank you!

Guest favorite

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.

Home in Germantown

4.92 out of 5 average rating, 176 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!

Guest favorite

A modern living area features a soft pink sofa embellished with decorative floral pillows. A glass coffee table is centered on a multi-colored area rug. Light enters from large windows outfitted with sheer curtains, creating a bright and inviting space. Artwork adorns the nearby walls.

Home in Louisville

4.93 out of 5 average rating, 182 reviews

Highlands Bishop Cottage-Walkable

Walkable Highlands Cottage in the Irish Hills neighborhood. Newly renovated with charm! Close to NULU (.5 mi), Butchertown (.6 mi), downtown (1 mi). Just 4 mi to the Yum Center, 5 mi to the Expo Center, 5.2 mi to Churchhill Downs, and 5.7 mi to the airport. Walkable to breweries, restaurants, parks and Cave hill Cemetery. You can even view the bridge over Ohio River from the end of the street. 1 on property small parking spot off alleyway with additional street parking on side streets

Top guest favorite

The living room features a spacious gray sectional sofa accompanied by a cozy throw. A decorative coffee table sits in the center, with a television mounted on the wall and a small side table with a lamp nearby. An ornate fireplace adds character to the space.

Home in Original Highlands

4.91 out of 5 average rating, 152 reviews

The Highland Fling - restaurant row, walk to all!

- ABSOLUTE BEST LOCATION!! LOUISVILLE'S RESTAURANT ROW!! - Sterilized Property - Superhost Property! - Charming house in Historic Highlands - 1 Block from Bardstown Rd - Restaurant Row - Walk to local shops and the BEST restaurants - Great backyard -1 full bath on first floor, one up -living room with sleeper sofa - Street parking for this residence - Fully stocked kitchen - 6.3 Miles to Churchill Downs - 2.8 Miles to Downtown/Convention Center - >1 Mile to Cherokee Park *NO locals*

Guest favorite

The home's inviting facade features white clapboard siding and large front windows adorned with classic trim. A welcoming entrance is highlighted by a beautiful door, surrounded by potted flowers and greenery. The well-maintained yard includes a small walkway that leads to the entrance.

Home in Original Highlands

4.9 out of 5 average rating, 185 reviews

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

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, 177 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 modern living area features a comfortable seating arrangement with plush couches beside a sleek glass coffee table. A flat-screen television is mounted above a gas fireplace, providing warmth and ambiance. Light floods the space through large windows, highlighting the stylish decor.

Home in Original Highlands

4.92 out of 5 average rating, 218 reviews

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

POSSIBLE CONSTRUCTION NOISE 5/15-6/15 MON-FRI 830AM-530PM Lux 3 story townhouse in city's best location. 1/2 block to great restaurants, cafes, shops and Cave Hill. Parking for 2 cars. 2 king bedrooms and 2 sleeper sofas. 3 bathrooms (2 full and a 1/2) Wifi, gas fireplace, cable, lux linens, washer/dryer, 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 min. walk.

Guest favorite

The exterior of a charming historic home is displayed, featuring a stone pathway and flower beds filled with colorful blooms. Two white curtains adorn the windows, while a wooden front door with a welcoming staircase is highlighted. An American flag gently sways above the entrance.

Home in Original Highlands

4.9 out of 5 average rating, 273 reviews

Urban Enclave! Convenient 1800s brick shotgun.

Tasteful and comfortable historic shotgun-style home in the Original Highlands, a dynamic and convenient neighborhood. Great location for the Urban Bourbon Trail, and cultural venues including Yum Center, Center for the Arts, Paristown Point, Fair Grounds, Lynn Family Stadium, Ballet, Symphony, and Opera. Downtown, NULU, and Butchertown are adjacent. Smoke-free, naturist home. Please read all information regarding the space and guest access.

Guest favorite

An inviting living area showcases two gray sofas positioned around a decorative area rug. Natural light fills the space through large windows with blue curtains. A brick accent wall complements modern appliances, and framed artwork adds a subtle touch of personality.

Home in Germantown

4.93 out of 5 average rating, 106 reviews

Cozy Two Bedroom Home in the Heart of Germantown

This beautifully renovated 2 bedroom home is conveniently located in the heart of Germantown near many of Louisville’s main attractions. Walking distance to Atrium Brewing Co., Trouble Bar, Logan Street Market, Full Stop Coffee Shop, and many other delicious eateries and bars. Short commute (5-10 minutes) to other attractions, including Churchill Downs, University of Louisville, KY Expo Center, downtown distilleries, and Bardstown Road.