House vacation rentals in Highlands

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Top-rated house rentals in Highlands

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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, 174 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!

Top guest favorite

A spacious interior showcases a multi-level layout with open sight lines. The upper area features a sleek railing and views of the large living space below, which includes modern furnishings and a dining area. Natural light floods through several windows, enhancing the airy atmosphere.

Home in Highlands

4.98 out of 5 average rating, 107 reviews

Highlands Lookout-3BR 3.5BA-Walk to Tons +Parking

Welcome to Highlands Lookout, your ultimate spot for a good time on Bardstown Road in the lively Highlands of Louisville! 3 Huge bedrooms plus 3.5 Baths. Perfect for guys' or girls' weekends, concerts, and conventions. Immerse yourself in the vibrant atmosphere of "Keeping It Weird." Unwind on our balcony or mix up a cocktail at our wet bar. Close to distilleries, bars with rare bourbons, downtown, racetrack, and the airport. Your gateway to a thrilling Louisville adventure! Off street Parking!

Top guest favorite

The exterior of the Shantyboathouse is presented, featuring a two-story blue structure with white trim and a welcoming patio area below. The backyard offers comfortable seating and a grill, while greenery lines the edges. The upper deck is accessible, providing additional outdoor space for relaxation.

Home in Butchertown

5 out of 5 average rating, 215 reviews

Butchertown & NuLu's Shantyboathouse

Welcome to the Shantyboathouse! Featured twice in the Courier-Journal, this property is uniquely one-of-kind and boasts a story even the Louisville Landmarks Commission couldn’t deny; which is why they awarded the property an historical plaque in 2019! The original newspaper article from 1976, the previous owners stated “The neighborhood legend about this house is that it just floated up the river in the ‘37 flood and somebody just built a foundation under it! They call it ‘the shanty boat’!

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, 188 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 modern living area features a soft pink sofa embellished with decorative floral pillows. A glass coffee table is centered on a multi-colored area rug. Light enters from large windows outfitted with sheer curtains, creating a bright and inviting space. Artwork adorns the nearby walls.

Home in Louisville

4.94 out of 5 average rating, 195 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

Top guest favorite

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.

Home in Highlands

4.91 out of 5 average rating, 162 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*

Top 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 Highlands

4.91 out of 5 average rating, 202 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.

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.

Home in Highlands

4.9 out of 5 average rating, 145 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.

Top guest favorite

An inviting living area showcases two gray sofas positioned around a decorative area rug. Natural light fills the space through large windows with blue curtains. A brick accent wall complements modern appliances, and framed artwork adds a subtle touch of personality.

Home in Germantown

4.94 out of 5 average rating, 115 reviews

Cozy Two Bedroom Home in the Heart of Germantown

This beautifully renovated 2 bedroom home is conveniently located in the heart of Germantown near many of Louisville’s main attractions. Walking distance to Atrium Brewing Co., Trouble Bar, Logan Street Market, Full Stop Coffee Shop, and many other delicious eateries and bars. Short commute (5-10 minutes) to other attractions, including Churchill Downs, University of Louisville, KY Expo Center, downtown distilleries, and Bardstown Road.

Guest favorite

A spacious living area is equipped with a large sectional sofa and a wooden coffee table, providing a comfortable gathering space. The modern kitchen features stainless steel appliances and dark cabinetry, while an open layout invites natural light from the adjacent windows.

Home in Germantown

4.94 out of 5 average rating, 141 reviews

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.

Superhost

A serene bedroom showcases a large bed with a decorative blue and white patterned blanket. A bedside table holds a lamp, and soft lighting enhances the calming atmosphere. There are curtains on the window, and wood flooring adds warmth to the space.

Home in Highlands

4.78 out of 5 average rating, 130 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

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, 404 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.