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Tyler Park Cottage in the Highlands

Adorable, light-filled cottage in the beloved Highlands neighborhood. An easy ten minute walk in one direction will put you on Bardstown Road, full of dining and bars, while a 15 minute walk in the other will land you in the hip Germantown-Schnitzelburg neighborhood. A short (6 minute) drive to downtown, 11 minutes to Churchill Downs. You'll find wireless internet, clean towels and sheets, basic kitchen and bathroom amenities, coffee maker, a flat screen TV with Apple TV, and keyless entry.

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Walk to the best spots Louisville has to offer.

Step into the warmth and character of this beautifully restored 1920s bungalow in Louisville’s beloved Historic Highlands. Thoughtfully updated for modern comfort while preserving its vintage charm, this space offers the perfect mix of history and hospitality. You’ll be just steps from the city’s best local restaurants, cafés, and boutiques. Downtown Louisville and NuLu are just minutes away. 5 ml to Churchill Downs Make this gem your home base for experiencing the best of Louisville

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!

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 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.

Cozy Studio close to Music Hall, Food, & Shops!

Come stay in our cozy & comfortable renovated 800 sq ft upstairs studio apartment of our historic Victorian home! Because of our close proximity to Louisville’s vibrant nightlife, the eclectic dining scene & shopping it’s no wonder visitors flock here to get a taste of something amazing! Walk down to the hottest Arts & Entertainment music hall- Old Forester Paristown Hall! Perfect Home base! Don’t forget about the Bourbon tours! We are the Napa Valley of Bourbon!*

Spacious unit near Downtown and 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. Minutes from Churchill Downs, perfect for the Derby festivities!

An Unhurried Stay in Butchertown · Steps from NuLu

Some places just make you feel held. This is one of them. A Jaclyn Journey Hospitality stay - set inside a 19th-century building on the edge of Louisville's Butchertown & NuLu neighborhoods. This apartment has been designed with the kind of care that's hard to put your finger on but impossible to miss. Every detail - from the original fireplaces to the lime-washed bedroom walls - has been chosen to make you feel genuinely at ease, not just comfortable.

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.

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.