Vacation rentals in Original Highlands, Louisville

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.

4.94 out of 5 average rating, 288 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.

Condo in East Market District

A modern kitchen island features a dark countertop and sleek stainless steel appliances. Wooden cabinetry complements the hardwood flooring. A circular mirror reflects light, enhancing the spacious feel. A wooden bench is positioned nearby, providing additional seating in the inviting area.

4.99 out of 5 average rating, 140 reviews

Downtown Apt in NuLu | King Bed w/ parking

This spacious NULU apartment combines modern furnishings with unique Louisville designs. You'll be staying in true urban style! This place is great for groups looking for a comfortable space to sleep and relax while being in the heart of NULU and just a quick ride to Louisville's major tourist destinations. You'll be steps away from bourbon distilleries, breweries, local restaurants, shopping, and Louisville's thriving nightlife. Includes free parking, work-friendly space, and high-speed wifi.

Condo in Original Highlands

4.93 out of 5 average rating, 199 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.

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.

4.94 out of 5 average rating, 156 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!

A kitchen corner features two wooden shelves adorned with plates, glassware, and decorative items against a vibrant floral wallpaper. A white coffee maker and a glass jar filled with ice sit on the marble countertop, contributing to a functional and inviting cooking space.

4.93 out of 5 average rating, 179 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

Home in Original Highlands

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.

4.9 out of 5 average rating, 184 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.

Apartment in Original Highlands

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.

4.91 out of 5 average rating, 156 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.

Loft in Central Business District

A cozy outdoor seating area is visible through large glass doors. The space features a comfortable dark wicker sofa set against a textured brick wall, accompanied by decorative wall plants. A soft area rug lies beneath, adding warmth to the inviting atmosphere.

4.97 out of 5 average rating, 834 reviews

Bourbon City Loft - Free downtown parking!

If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

4.98 out of 5 average rating, 107 reviews

Condo in Butchertown

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.

Apartment in Original Highlands

4.93 out of 5 average rating, 176 reviews

Cozy Studio close to Music Hall, Food, & Shops!

Come stay in our cozy & comfortable renovated 800 sq ft upstairs studio apartment of our historic Victorian home! Because of our close proximity to Louisville’s vibrant nightlife, the eclectic dining scene & shopping it’s no wonder visitors flock here to get a taste of something amazing! Walk down to the hottest Arts & Entertainment music hall- Old Forester Paristown Hall! Perfect Home base! Don’t forget about the Bourbon tours! We are the Napa Valley of Bourbon!

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.

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. .

Apartment in East Market District

A well-organized kitchen corner features open shelving adorned with various plates, glasses, and decorative items. Below, a white stove and microwave are accompanied by a coffee maker and utensils, providing a functional yet aesthetically pleasing space. Natural light enters through the window, brightening the area.

4.98 out of 5 average rating, 160 reviews

Dreamy, Designer-Curated Shoppable Retreat

A thoughtfully curated rental by Jaclyn Journey Hospitality, designed with intention to make you feel taken care of when staying away from home. Featured in Architectural Digest, DOMINO magazine, Apartment Therapy & others. With every item hand-selected to enchant the senses, this rental is shoppable, encouraging you to take your favorite piece of your trip back with you.

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Popular amenities for Original Highlands, Louisville vacation rentals

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Free parking on premises

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Other great vacation rentals in Original Highlands, Louisville

Apartment in Original Highlands

An exterior staircase made of wooden steps leads to a private entrance, surrounded by red brick walls. A clear blue sky is visible above, with leafy trees providing a touch of greenery nearby. The stair area is well-lit and inviting.

4.97 out of 5 average rating, 30 reviews

Historic Highlands/NULU Retreat

TreyRating, 5 stars3 days ago

This place was clean, homey and even more adorable than the photos show. Super close to restaurants and easy to get around. Hope to stay again!

A spacious kitchen area showcases granite countertops and modern appliances. Natural light fills the space through large windows, highlighting the wooden flooring. High-top bar stools are positioned at an island, while a decorative wall and greenery add a touch of character to the inviting ambiance.

5 out of 5 average rating, 9 reviews

Colonel Lou Lou's

DevinRating, 5 stars1 day ago

Perfect place to take a rest stop when passing through Louisville. Was clean and comfortable. Thanks Steven :)

Apartment in East Market District

A window with a clear view of the downtown street below is set within an arched frame. A small potted plant sits on the windowsill, adding a touch of greenery to the scene. Soft curtains drape elegantly beside the window.

5 out of 5 average rating, 29 reviews

Top of the Brick Penthouse Suite

ScottRating, 5 stars1 week ago

Great place for 2 people to enjoy Louisville. Good location, clean, well-appointed. We would reserve this again without hesitation.

A cozy outdoor firepit area is surrounded by four red Adirondack chairs on a gravel base. The firepit, made of stone, features an inviting flame. Soft lighting is strung above the deck, adding ambiance to the backyard space.

5 out of 5 average rating, 47 reviews

Convenient & Cozy! Close 2 it all in Louisville!

AllisonRating, 5 stars2 weeks ago

Home was exactly as described— very clean, clear instructions for check in and check out. Nice quiet neighborhood close to downtown and all the distilleries and restaurants. Would definitely stay here again.

A keypad door lock is mounted on a dark door, featuring numbered buttons for entry codes. The surface is smooth, and a keyhole is positioned below the keypad. A window can be seen in the background with blinds partially open, allowing light to filter through.

5 out of 5 average rating, 61 reviews

Nature's Edge-An Oasis in the Highlands

MoiraRating, 5 stars1 month ago

Heather was an excellent host and a good communicator. Her place is very comfortable and beautifully furnished. The bed was comfy and there were some nice welcoming touches - some treats, plenty of tea and coffee and a couple of fresh flowers in the kitchen. It was pleasant relaxing on the front patio. Plenty of good restaurants and Cherokee Park are within walking distance.

Private room in Original Highlands

4.97 out of 5 average rating, 575 reviews

Charming Home In The Highlands

KatieRating, 5 stars3 weeks ago

To say this place is “charming” is a total understatement! We felt right at home for the short bit of time we stayed. The fan was awesome, the water pressure was great and access to drinking water was ideal after a hot concert. Tracy and her cats Jack and Patrick were lovely hosts! If we ever find ourselves in Louisville again we will be checking this place first! The house was adorable and in a perfect spot, walkable to Paristown Hall and many little places to eat! Would stay here a thousand times if I could!

A close-up view of a keypad lock is presented. A finger is seen pressing the number 78. The lock is mounted on a light purple surface, accompanied by subtle splashes of color.

4.86 out of 5 average rating, 35 reviews

Funky Highlands apartment

paulRating, 5 stars3 days ago

Brian's place was exactly as described. The room was dark; the ac was ice box' Esque, and the bed was very comfortable. I slept like a king!