House holiday rentals in Original Highlands, Louisville

4.95 out of 5 average rating, 267 reviews

Kentucky Hug: A Modern Shotgun for Bourbon Elites

A “Kentucky Hug” is the warm feeling one gets after sipping whiskey. Get that feeling at this renovated shotgun home in centrally and conveniently-located Irish Hill! One block away from Baxter Ave-- the original Highlands! One mile to a few urban bourbon distilleries. A quick Lyft to NULU, Butchertown, Clifton, the convention center, and KFC Yum Center. Easy access to I-64, I-65, and I-71. Walking distance to Headliners Music Hall, Gravely Brewing, and other great eats. Permit No: STR926031

4.98 out of 5 average rating, 102 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!

4.95 out of 5 average rating, 134 reviews

The Burb Inn - Near Nulu and Downtown

The Burb Inn is a hip place to stay in the Phoenix Hill/NULU district of Louisville. Walking distance to top rated restaurants, bars, and attractions. Great place to host a group of friends, family or smaller bachelor party. Includes private yard & fire pit as well. Upon entering there is a living area perfect for entertaining with 16’ ceiling & sleeping loft above the kitchen area. Upstairs has two bedrooms with queen beds each with private half bath. There is a separate private shower room.

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!

4.93 out of 5 average rating, 181 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

4.98 out of 5 average rating, 358 reviews

Velo Studio Flat / Paristown Pointe / Highlands

Next to the The Highlands, this bike friendly house is in Paristown Pointe with great restaurants, Louisville Stoneware & an easy walk to Baxter & Bardstown Rd for nightlife. A clean, comfortable & stylish home in a quiet area. Four bicycles to access scenery nearby with a relaxing screened porch to unwind. Perfect for athletes, couples, families or business travelers. Cherokee Park is close with plenty of woods with trails for biking & hiking. Downtown, Big 4 Bridge & waterfront just 2 mi.

4.91 out of 5 average rating, 152 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*

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.

4.87 out of 5 average rating, 176 reviews

Prime Highlands Location - 500ft fro. Midcity Mall

Formerly known as Breslin House, this well-loved Airbnb (126 five stars reviews) is under a new host. We are confident you'll love it as much as everyone did before! Our house is located on a quiet street, but steps away from restaurants, bars, boutiques, and cafes on Bardstown Rd. It's perfectly situated in the heart of the Highlands so you can walk to almost everywhere. Our home is very spacious with 3 large bedrooms, so you'll have plenty of privacy even with a large group.

4.96 out of 5 average rating, 270 reviews

Home in Germantown

Bourbon Belle- A Germantown Favorite! Priv Parking

The Bourbon Belle is a newly renovated historic shotgun home in the heart of Louisville's Germantown neighborhood. Lots of natural light and tall ceilings make your stay feel comfy and warm just like home. Sleeps 4 comfortably and has 1.5 bathrooms. W/D. 2 Smart 55" TVs. High speed internet. Parking pad in back for 2 cars. Centrally located, close to Downtown, U of Louisville, KY Fair &Expo Center, Louisville Airport, and only 3.2 miles away from Churchill Downs.

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.