Vacation rentals in Highlands

4.95 out of 5 average rating, 331 reviews

A modern kitchen features dark cabinetry and a large island with seating for two. Natural light pours in through a window, illuminating the white subway tile backsplash and stainless steel appliances. Wooden ceiling beams add character to the airy space.

Apartment in Louisville

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

ValueFamilyComfort

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

ValueFamilyCheck-in

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.

ValueLocationIndoor spaces

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!

FamilyLocationLayout

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*

LocationFamilyComfort

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.

FamilyValueHospitality

Superhost

A well-lit living area features a gray sectional sofa and a mounted television. Natural light enters through large windows lined with sheer curtains. A dining table is positioned in the background, complemented by chairs and a glimpse of the kitchen area.

4.78 out of 5 average rating, 125 reviews

The Bardstown-Louisville Nightlife

This spacious unit provides a front row seat to watch and experience Louisville from the comfort of your own private retreat in the middle of the best street in Louisville. Feet from many restaurant , bars and boutiques. During your stay spend time walking the neighborhood filled with boutiques, restaurants, bars, distilleries and art galleries. Start the bourbon trail or walk to the famous Cave Hills Cemetery. Private gatherings are allowed but house rules must be followed.

LocationFamilyParking

4.98 out of 5 average rating, 336 reviews

A charming balcony features a wooden table surrounded by four slatted chairs. A potted fern hangs gracefully from the angled ceiling, with views of lush greenery visible beyond the railing, creating a serene outdoor space.

Guesthouse in Louisville

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

ValueFamilyCheckout

Superhost

A comfortable living area showcases a large sectional couch in a soft blue hue, complemented by colorful cushions and artwork hanging on the wall. Plush rugs add warmth underfoot, while a table with books sits at the center, inviting relaxation.

4.83 out of 5 average rating, 199 reviews

Highlands Midcentury Getaway w/ Firepit & King Bed

Welcome to "Ruby"- the coolest, most conveniently located home in the city. From head to toe, Ruby is decked out with all the ingredients for a fun, relaxing Louisville stay. Occupying the first floor of a beautiful Victorian home, Ruby is walking distance to restaurants and the urban bourbon trail, as well as hospitals and downtown businesses. The location truly can't be beat! Drive or Uber to the Yum center, NULU, Lynn Family Stadium, and the waterfront in no time.

FamilyLocationBathroom

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.

ValueLocationLayout

A modern living area is highlighted by a spacious grey sofa adorned with patterned cushions. A simple coffee table is placed on a textured rug, while an art piece and soft lighting from pendant fixtures enhance the ambiance. Green chairs invite relaxation, complementing the overall decor.

4.9 out of 5 average rating, 116 reviews

Private Highlands Apt • Free Parking • Walkable

Enjoy a stay in a beautiful modern apartment right in the heart of Highlands. Located on lively Baxter Avenue, you’re steps from top local restaurants, bars, and charming mom-and-pop shops. Walk everywhere, grab amazing food, and enjoy the nightlife. Downtown and 4th Street Live are just a few minute drive away. End the night unwinding with complimentary movie streaming in a cozy, stylish space.

LocationValueKitchen

A cozy living area features a comfortable sofa adorned with decorative pillows. A sleek coffee table sits in the center, complemented by two dark armchairs. Artworks hang on the wall above, while a statement light fixture and a decorative mirror add elegance to the space.