Vacation rentals in Original Highlands, Louisville

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Top-rated vacation rentals in Original Highlands, Louisville

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Guest favorite

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 Cherokee Triangle

4.94 out of 5 average rating, 289 reviews

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.

Guest favorite

A bright living room is furnished with a gray sofa and two blue armchairs. A glass coffee table is centered on a colorful area rug. A flat-screen TV sits on a wooden console, and a bookshelf is visible, filled with various books. Natural light enters through multiple windows.

Cottage in Germantown

4.86 out of 5 average rating, 319 reviews

Tyler Park Cottage in the Highlands

Adorable, light-filled cottage in the beloved Highlands neighborhood. An easy ten minute walk in one direction will put you on Bardstown Road, full of dining and bars, while a 15 minute walk in the other will land you in the hip Germantown-Schnitzelburg neighborhood. A short (6 minute) drive to downtown, 11 minutes to Churchill Downs. You'll find wireless internet, clean towels and sheets, basic kitchen and bathroom amenities, coffee maker, a flat screen TV with Apple TV, and keyless entry.

Top guest favorite

A comfortable living area features a gray sofa adorned with decorative pillows, alongside a matching armchair. A wooden coffee table sits in the center, complemented by a cowhide rug. The open layout showcases a dining area with a round table, and a fully equipped kitchen is visible in the background.

Apartment in Germantown

4.93 out of 5 average rating, 125 reviews

Vintage yet Modern Highlands home! Walk to venues!

Spacious 1st floor apartment in a Victorian duplex home in the heart of the Highlands/Germantown. We are ready to host for short, mid & long term! Because of our close proximity to Louisville’s vibrant nightlife, eclectic dining scene & shopping it’s no wonder visitors flock here to get a taste of something amazing! Perfect place for your Ky Derby home base! Walk down to the hottest Arts & Music venue in town- Old Forester Paristown Hall! Don’t forget about the Bourbon tours and new breweries!

Guest favorite

A modern living area is depicted, featuring a white built-in shelf surrounding a gas fireplace. Above the fireplace, a flat-screen television displays various streaming options. The shelves are adorned with decorative items and storage baskets, adding organization to the space.

Condo in Original Highlands

4.93 out of 5 average rating, 201 reviews

Large Townhouse, Walk to All! King beds, 2.5 baths

Large, 3 story townhouse sleeps 6 in 1600 sq. ft. Step out the door to best walking neighborhood in Louisville. Great coffee shop 150 ft. away, with a dozen places to eat, from fancy to casual, within the block. Parks, movies, live music are 10 minute walk or less away. 2 King bedrooms, each with full bath, 1 queen and 1 twin daybed w/ trundle. Fully equipped kitchen, 3 large smart tvs, wifi and cable! Kitchen fully equipped, from quality appliances to pots/pans/plates/cutlery/glasses/etc.

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 Cherokee Triangle

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

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 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.

Apartment in Original Highlands

4.91 out of 5 average rating, 157 reviews

Highlands Midcentury Getaway w/ Firepit & King Bed

NEW LISTING! 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.

Top guest favorite

A unique hanging chair with plush cushions sits beside a glass coffee table. The table is adorned with orange dishware holding lit candles and crystals. Colorful reflections are cast across the room, highlighting the vibrant decor and inviting atmosphere.

Apartment in Louisville

4.95 out of 5 average rating, 132 reviews

Highlands Zen Oasis • Comfy, Clean & Cozy

Awesome Sweet Spot of a Louisville Location! This PRIVATE APT. with SELF CHECK IN + FREE PARKING is in a beautiful, safe neighborhood in the historic Highlands. Quick 2-min walk to magnificent Cherokee Park OR charming Bardstown Road - a multitude of eclectic galleries, bars, restaurants & shops to explore! Conveniently (5-10 min) located to Churchill Downs, Downtown Louisville, Louisville Seminary, NuLu, UofL, Bellarmine, Fair & Expo Center, Yum Center, Waterfront & the Airport⚜️

Top guest favorite

A well-equipped kitchen showcases light cabinetry against a black ceiling. A dining table with four chairs is positioned by a window, while open shelves display dishware and cooking essentials. An industrial-style light fixture hangs above the room, enhancing its bright and functional layout.

Condo in Clifton

4.98 out of 5 average rating, 108 reviews

The Hilltop Hideaway

Come hunker down at The Hilltop Hideaway, a centrally-located historic 19th-century shotgun style cottage perched atop Clifton’s hills. Perfect for a couple’s getaway, a friends’ rendezvous, or a creative’s retreat, you may find yourself not wanting to leave. But the location couldn’t be better, with Frankfort Ave’s restaurants, coffee shops, and bars all within walking distance, and nearby entertainment options plentiful with Butchertown and NULU only minutes away.

Guest favorite

A modern kitchen features navy blue cabinetry paired with white tiled backsplashes. Stainless steel appliances, including an oven and microwave, are complemented by a gold faucet. A large window allows natural light, reflecting off the light countertops and showcasing the organized space.

Tiny home in Louisville

4.96 out of 5 average rating, 170 reviews

Trendy Tiny Home w/ King Bed Loft

Unique experience in style! Enjoy a weekend or an extended stay at this charming carriage house just walking distance to popular restaurants, breweries and local shops. The location is perfect! Inside you'll find a fully equipped kitchen, bathroom, living room with a 55" smart tv, a dedicated work space/desk and a king sized bed in the loft. Guests will have privacy with self-check in smart locks and a dedicated parking space. We can't wait to host you!

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

A spacious studio is illuminated by natural light from multiple windows. Wood flooring adds warmth to the space. A cozy sleeping area features a bed, while a stylish kitchen with a central island and modern appliances is visible. A ceiling fan provides added comfort.

Apartment in Louisville

4.96 out of 5 average rating, 140 reviews

Sun-filled Phoenix Hill Studio

Located in the Phoenix Hill neighborhood, it's a short 11 minute walk to East Market District restaurants and attractions or a 15 minute walk to Gravely and other Original Highlands destinations. 11 minute drive to Churchill Downs 5 minute drive to the Highlands 4 minute drive to East Market restaurants and shopping. Ample Lyft and Uber drivers in this neighborhood to take you anywhere you want to go. .