Vacation rentals in Highlands

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Top-rated vacation rentals in Highlands

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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, 299 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 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

4.92 out of 5 average rating, 186 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! *

Top guest favorite

A contemporary exterior features a striking navy blue facade with geometric accents. Two entrance doors are framed by lush greenery, including neatly trimmed shrubs and tall grasses. Large windows allow natural light to fill the interior, while architectural details highlight the property's modern design.

Guest suite in Cherokee Triangle

4.97 out of 5 average rating, 143 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.

Top 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, 168 reviews

2 br home, walking distance to much entertainment

Home 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 and Nulu are a very short drive away, many great bars and distilleries are walking distance. Home built in 1879, entirely renovated with a modern kitchen, fully fenced backyard, private parking and fire pit.Master bedroom has a king size bed and it’s own bathroom with jetted tub. We look forward to your visit, thank you!

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 Highlands

4.93 out of 5 average rating, 211 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.

Superhost

Home in Germantown

4.89 out of 5 average rating, 110 reviews

Cozy 2nd-Floor Home | Prime Location 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. Enjoy historic character, modern amenities, and easy access to top attractions. Book now!

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.

Apartment in Highlands

4.9 out of 5 average rating, 167 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.

Top guest favorite

A spacious bedroom features a large bed with dark bedding centered on wooden floors. Two cozy armchairs are positioned nearby, complemented by a vibrant area rug. A decorative mirror and framed artworks adorn the walls, while a bookshelf holds an array of books, adding character to the space.

Guesthouse in Schnitzelburg

4.96 out of 5 average rating, 237 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

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 Highlands

4.89 out of 5 average rating, 278 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.

Top guest favorite

A blue carriage house is viewed from the driveway, surrounded by greenery and blooming trees. Steps lead to an upper balcony, offering outdoor potential. The driveway provides easy access to the garage, emphasizing a sense of space and privacy.

Guesthouse in Louisville

4.92 out of 5 average rating, 1,069 reviews

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

Superhost

A well-equipped kitchen features dark cabinetry and a spacious granite countertop. Decorative elements, including wall art and a clock, add personality. Pendant lights illuminate the area, while a small coffee maker sits on the countertop. A wooden dining table is visible in the background.

Home in Highlands

4.87 out of 5 average rating, 141 reviews

Convenient and Walkable area | 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

Top guest favorite

The kitchen area is characterized by white cabinetry and granite countertops, reflecting natural light from a nearby window. Stainless steel appliances are featured, along with two wooden stools at the breakfast bar. A small round dining table with two chairs is positioned to the side.

Home in Cherokee Triangle

4.97 out of 5 average rating, 402 reviews

The Highlands Condo/Roof Deck

Our brand new renovated 1 BR 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 area, 12 minutes from the airport. Walking distance to many great restaurants, bars, shops , and parks.