House vacation rentals in Highlands

4.9 out of 5 average rating, 614 reviews

Walk to everything • Quiet, Private, and Cozy

Tucked along a quiet, tree-lined street in Louisville’s Original Highlands neighborhood, you’ll find a cozy, private retreat filled with character and unique decor. Featuring a large master bedroom with king Sleep Number bed, a spacious living/dining room area, 2 full bathrooms, and a cozy full sized guest room. Walk to the best restaurants, boutiques, and coffee shops. Explore the nearby parks or unwind in your peaceful, historic hideaway. 1 mile from NULU 2 from downtown 5 from the Downs

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The living room features a comfortable grey sectional couch and an accent chair positioned around a decorative fireplace with a stone surround. A flat-screen TV is mounted above the mantle, while natural light enters through large windows adorned with soft curtains.

4.98 out of 5 average rating, 106 reviews

Spacious Highlands Home-King Bed, Fire Pit & Yard

Tucked in the beautiful, historic Highlands, this spacious, pet-friendly 3-bedroom, 2-story home is minutes from the action! Grab a quick Uber to some of the most popular spots, such as the Bourbon Trail, coffee shops, or Nulu, then return to your relaxing, fully-fenced backyard oasis. Perfect for groups exploring the city by day and relaxing by the fire pit at night! Enjoy the best of both worlds with fast WiFi and a dedicated workspace if you need to log on remotely! Sleeps 8 and a king bed.

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4.94 out of 5 average rating, 226 reviews

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

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

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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.

4.95 out of 5 average rating, 122 reviews

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

Experience the best of Louisville from the heart of the Highlands on iconic Bardstown Road! 3/4 Bedrooms • 3.5 Baths Bonus Lounge with Queen Sleeper Sofa Private Balcony & Wet Bar Perfect for Bourbon Tours, Concerts, Bachelor/Bachelorette Trips & Group Getaways Off-Street Parking Walk to Louisville's best restaurants, bars, breweries, coffee shops, and nightlife. Minutes from downtown, distilleries, Churchill Downs, and the airport. Stylish, spacious and designed for memorable stays!

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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.

4.92 out of 5 average rating, 184 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*

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4.98 out of 5 average rating, 372 reviews

A bright living area features a red sofa styled with decorative pillows, accompanied by two white accent stools. A uniquely designed coffee table with colorful artwork is positioned in the center. Hardwood floors and a patterned wall art enhance the welcoming space.

Home in Louisville

Velo Studio Flat / Paristown / Highlands /

Next to the The Highlands, this bike friendly house is in Paristown with great restaurants, Louisville Stoneware & an easy walk to Baxter & Bardstown Rd for nightlife. A clean, comfortable & stylish home in a quiet area. Five bicycles to access scenery nearby with a relaxing screened porch to unwind. Perfect for athletes, couples, families or business travelers. Cherokee Park is close with plenty of woods with trails for biking & hiking. Downtown, Big 4 Bridge & waterfront just 2 mi.

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The living area features a comfortable sofa adorned with decorative cushions, set against a backdrop of large windows with colorful stained glass accents. A contemporary television is mounted on the wall, while a rustic coffee table sits atop an ornate area rug, accompanied by a cozy armchair.

4.91 out of 5 average rating, 199 reviews

Historic Hideaway w/Free Parking

Situated in the heart of a vibrant neighborhood, you'll find an array of exciting options for dining, drinks, coffee, and shopping right at your doorstep. With numerous restaurants serving diverse cuisines, trendy breweries offering craft beers, cozy coffee shops brewing aromatic blends, and chic boutiques showcasing local fashion and artisanal goods, you'll have plenty of choices to explore and indulge in the local scene. You'll be spoiled for choice with the plethora of options.

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A welcoming living area features a large flat-screen TV mounted above an ornate fireplace. Two comfortable leather sofas are arranged around a glass coffee table on a patterned area rug. The space is illuminated by a modern chandelier, with natural light filtering through sheer curtains.

4.95 out of 5 average rating, 314 reviews

Eclectic Historic House in the Highlands

Situated in the Highlands neighborhood, our large 1900 Victorian duplex is the perfect retreat for you and your group during your next visit to the Derby City! Our home sits on a quiet street, just a few minutes’ walk away from Baxter Ave/Bardstown Rd, which offers ample bars, restaurants, and night clubs. Our home is also just a short drive to downtown/waterfront, UoL's campus/Churchill downs, the airport, and other great Louisville neighborhoods. We can’t wait to have you!

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4.89 out of 5 average rating, 199 reviews

Home in Germantown

Spacious unit near Downtown and Bourbon Trail!

Discover Louisville’s charm in this renovated brick building, perfectly located near downtown, Paristown Hall, the Expo Center, airport, NuLu, and the Highlands. This cozy 2nd-floor flat offers privacy with a private entrance, fenced yard, and self check-in. Ideal for Bourbon Trail adventurers, families, or business travelers, it features high-speed Wi-Fi, a fully equipped kitchen, and free parking. Minutes from Churchill Downs, perfect for the Derby festivities!

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5.0 out of 5 average rating, 146 reviews

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.

Home in Louisville

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.

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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.

4.89 out of 5 average rating, 290 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.

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