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 Louisville

4.94 out of 5 average rating, 285 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 welcoming entrance is highlighted by a set of stone steps leading to a covered porch. Vibrant flowers enhance the greenery, while elegant architectural details are seen on the house. The porch features a decorative railing and a couple of seating areas for relaxation.

Apartment in Louisville

4.83 out of 5 average rating, 129 reviews

Highlands Harmony House - Near Cherokee Park

Upstairs; full sized Studio Apartment with large bedroom, kitchen, separated bath, private, big screened porch! The PRIVATE bathrooms are in the hall -3 feet from your bedroom/hidden behind privacy screens. "Yes, you can run to the bathroom in your 'all-together!" You'll love the kitchen and comfortable queen bed. Very cozy! Private screened porch overlooks our artistic/wooded backyard! Located on a quiet dead end street. Stroll our shady sidewalks to local bars coffee shops, restaurants etc.

Top guest favorite

A modern entrance is showcased with a sleek black door featuring decorative panels. Lush greenery and blooming hydrangeas frame the stone pathway, which leads towards the door. Subtle outdoor lighting enhances the welcoming atmosphere as the pathway is bordered by neatly arranged stones.

Guest suite in Louisville

4.97 out of 5 average rating, 137 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Guest favorite

A modern ceiling fan is featured with a circular design and multiple wooden blades. The fan's central light fixture provides illumination, while the sleek, black frame complements the rustic wooden accents.

Home in Louisville

4.94 out of 5 average rating, 152 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

4.93 out of 5 average rating, 171 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 deck area is featured, furnished with two comfortable chairs and a small table. Decorative cushions with floral patterns are placed on the chairs. A rug with a geometric design enhances the space, which is surrounded by wooden railing and overlooks a green yard.

Home in Original Highlands

4.91 out of 5 average rating, 180 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 welcoming display is situated within an alcove, featuring a black letter board that reads 'Welcome to Ruby, Louisville KY, Have Fun!' A small potted plant adds a touch of greenery. Nearby, a plush throw pillow and modern seating are partially visible.

Apartment in Original Highlands

4.91 out of 5 average rating, 155 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

Apartment in Louisville

4.95 out of 5 average rating, 129 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

Condo in Butchertown

4.98 out of 5 average rating, 101 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 close-up view of a modern electronic door lock is presented on a wooden door. The keyless entry system features a keypad with numbered buttons, ensuring secure access to the space.

Apartment in Louisville

4.96 out of 5 average rating, 139 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. .

Guest favorite

A winding road is lined with lush, green trees casting dappled shadows. The asphalt has a double yellow line, guiding the way through a tranquil, wooded area. Sunlight filters through the foliage, creating a serene ambiance.

Apartment in Original Highlands

4.88 out of 5 average rating, 161 reviews

Walk to Bars & Restaurants | 1BR Highlands Stay

Prime Location in Louisville’s Most Walkable Area! Just 7 minutes to the KFC Yum! Center with dedicated parking and steps from hundreds of shops, bars, and restaurants. This comfortable, well-equipped home offers exceptional value for your stay. Enjoy: •Easy self check-in with keypad •Photo-guided check-in instructions •Stocked kitchen for cooking •Roku TV & free Wi-Fi

Guest favorite

The exterior of a newly renovated two-story home is highlighted, featuring a blue facade and multiple large windows. Warm light emanates from within, illuminating the entrance. A neatly landscaped pathway leads to the front door, bordered by small bushes and plants in the front yard.

Apartment in Louisville

4.93 out of 5 average rating, 265 reviews

The Highlands Original Condo

Our brand new renovated 1BR condo is located in a famous Highlands' neighborhood. Conveniently located about 5-8 minutes from Churchill Downs, KFC Yum Center, Cardinal Stadium, Convention Center, Center for the Arts, Downtown Distilleries, NuLu&Germantown areas, 12 minus from the airport. Walking distance to many great restaurants, bars, shops, and parks.