House holiday rentals in Highlands

Walk to everything • Quiet, Private, and Cozy

Tucked along a quiet, tree-lined street in Louisville’s Original Highlands neighborhood, you’ll find a cozy, private retreat filled with character and unique decor. Featuring a large master bedroom with king Sleep Number bed, a spacious living/dining room area, 2 full bathrooms, and a cozy full sized guest room. Walk to the best restaurants, boutiques, and coffee shops. Explore the nearby parks or unwind in your peaceful, historic hideaway. 1 mile from NULU 2 from downtown 5 from the Downs

Spacious Highlands Home-King Bed, Fire Pit & Yard

Tucked in the beautiful, historic Highlands, this spacious, pet-friendly 3-bedroom, 2-story home is minutes from the action! Grab a quick Uber to some of the most popular spots, such as the Bourbon Trail, coffee shops, or Nulu, then return to your relaxing, fully-fenced backyard oasis. Perfect for groups exploring the city by day and relaxing by the fire pit at night! Enjoy the best of both worlds with fast WiFi and a dedicated workspace if you need to log on remotely! Sleeps 8 and a king bed.

Cheerful Highlands Home with Parking*Cherokee*NuLu

A Modern 1900s Bungalow in the Prime Location for a true Louisville experience. This 3bed/2bath home is thoughtfully & comfortably furnished to make your stay memorable. A gracious front porch & patio for relaxing. Walkable to nearby pubs and restaurants. Off street parking. A wonderful place to stay! 0.6miles to Paristown Pointe 4min to Angels Envy 7min to ConventionCenter 8min to YUM Center 14min to Louisville SDF Airport 14min to Kentucky Exposition Center 13min to Churchill Downs Track

The Shotgun Rye! Your Bourbon home near Downtown

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!

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

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

Experience the best of Louisville from the heart of the Highlands on iconic Bardstown Road! 3/4 Bedrooms • 3.5 Baths Bonus Lounge with Queen Sleeper Sofa Private Balcony & Wet Bar Perfect for Bourbon Tours, Concerts, Bachelor/Bachelorette Trips & Group Getaways Off-Street Parking Walk to Louisville's best restaurants, bars, breweries, coffee shops, and nightlife. Minutes from downtown, distilleries, Churchill Downs, and the airport. Stylish, spacious and designed for memorable stays!

Velo Studio Flat / Paristown / Highlands /

Next to the The Highlands, this bike friendly house is in Paristown with great restaurants, Louisville Stoneware & an easy walk to Baxter & Bardstown Rd for nightlife. A clean, comfortable & stylish home in a quiet area. Five 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.

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*

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.

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

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.

Walk to Bars & Restaurants! | Budget Friendly!

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