Holiday rentals in Highlands

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.

Bourbon Trail Spacious Backyard NEW HotTub Grill!

The Burnt Barrel, discover your vibrant Louisville getaway! Perfect for couples, business travelers, or event visitors, this cozy home offers high-speed Wi-Fi and a dedicated workspace, fully equipped kitchen, and a NEW hot tub and grill for you to enjoy! Guests rave about its comfort, walkable location, and modern amenities. Enjoy nearby bars and restaurants all just minutes from downtown, UofL Health, and the Convention Center. Experience true Louisville charm and convenience! Book a stay now!

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

Cozy Craftsman in the Historic Highlands

Welcome to your cozy getaway in the heart of Louisville’s beloved Highlands neighborhood. This 2nd floor apartment sits in a beautiful 1917 Craftsman bungalow. Whether you’re visiting for a weekend getaway, a festival, or to explore Louisville’s food & bourbon scene, this historic Highlands home offers the perfect blend of comfort, character, & location. You’ll be just steps from the city’s best local restaurants, cafés, and boutiques. NuLu - 1 mi Downtown - 2 mi Churchill Downs - 5 mi

Nulu | Bourbon District | 4 Bedroom | Fire Pit

Enjoy your stay in this clean and comfortably modern home that's right next to all the hotspots NuLu has to offer! Socialize in the evenings around the fire pit, in the private fully fenced back yard, or catch the game on a 65 inch 4K LED TV. Don't want to stay in? Walk or take a short Uber to places like Falls City Brewing, Guaca Mole or La Bodeguita De Mima! With 2 King beds, 1 Queen bed, 1 Full bed, and two living spaces, this home provides room for everyone to relax and make memories!

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

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.

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.

Highlands Airy Retreat- No Hassle Checkout

Welcome to "Birdie". The cutest, most conveniently located home in the city. From head to toe, Birdie is decked out with all the ingredients for a fun, relaxing Louisville stay. Occupying the 2nd floor of a beautiful Victorian home, Birdie 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.

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

1 Bedroom Apt in Highlands Home w/private patio

This Highlands apartment is located in Louisville’s historic Cherokee Triangle neighborhood. It is a five minute walk from some of the best restaurants, bars, parks and shops in the city. The apartment has 1 bedroom with a comfy queen size bed and a full size day bed in the office alcove! The kitchen is equipped for all of your cooking needs. After exploring the city, enjoy relaxing on the private patio with its outdoor day bed!

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.