Mansion holiday rentals in Louisville

★WorldlyHighlands★LARGE Kitchen, FASTWifi, Parking

Upper Highlands home in privileged location w/ keyless entry. A block from Bardstown Road, close to I-264 for fast commutes and all the HIGHLANDS excitement. Harmony of convenience & quiet allows for perfect stays for families, couples, business/vacation travelers alike. •4 bedrooms (includes basement), ALL WITH SMART TVs •Large kitchen, appliances, 2019-23 •PARKING up to 4 cars •Back porch GAS GRILL •Patio furniture * FIRE PIT, added Oct-2024 •Super Fast fiber-optic WiFi •Samsung Washer&Dryer

Pet Friendly Home In The Highlands

This 1700 sq ft. vintage bungalow is ideally located and equipped with everything you need to enjoy your stay in Louisville. Established in The Highlands, a historic area comprised primarily of older homes, varying in style, size and quality, close to all amenities, shopping, parks, public transportation & recreation. The area is packed with walkable restaurants, bars, and shops, and is centrally located to all city attractions, including Churchill Downs, the Yum! Center, and the waterfront.

HISTORIC Home in Old Louisville 4BR/2BA w DECK

Beautiful home centrally located-close to EVERYTHING! This elegant home has original stained glass windows, beautiful woodwork, large dining and living rooms with two full kitchens and access to a spacious 2 level deck. Super comfortable beds make this a relaxing stay. Close to all the Urban Bourbon restaurants and Distilleries. Minutes from U of L, Churchill Downs, 4th Street Live, Main Street attractions, YUM Center, Convention Center and many other wonderful Louisville destinations.

FAB Trackside by the Backside, TONS of PARKING!

Brand new to Airbnb, you can be one of our first guests! Welcome to Churchill Downs, The KY EXPO, and UofL! Greetings from Trackside by the Backside! Whether your hosting a visit to the bourbon trail or have business at the EXPO or downtown, this 6 BR, 3 bath home is the perfect spot! Convenient to the expressway, the airport, downtown and I-65, Trackside by the Backside is close to all! Walk to Kroger, restaurants and historic Churchill Downs!!! Book now & secure your vacation dates!

Fully Renovated 1960s Urban Chic Deer Park Retreat

Sprawl out on a chic, mid-century sectional amid the retro flair, eclectic artwork, and vaulted ceilings within this captivating loft-style home. Cook dinner in a kitchen with soapstone surfaces and dine al fresco at an old-school table on the patio. Completely renovated with all new luxury hotel bedding, while keeping the original hardwoods, and charm of this older home. Two bedrooms on the 1st floor and two on the 2nd, easy access for all ages. 10 min, to downtown and the Expo Center.

Waterfront,Hot Tub,Sauna,Firepit,Cinema,Pets,Views

Derby 2026 dates available. Enjoy luxury riverfront living at Maya’s Bourbon Riverfront just 15 minutes from Churchill Downs and minutes from downtown Louisville and Jeffersonville. Ideally located on the Bourbon Trail this upscale retreat offers four bedrooms three baths and thoughtfully designed spaces for relaxing or entertaining. Start your day by the river then enjoy Derby festivities iconic distilleries NuLu dining and nightlife for an unforgettable Derby and Bourbon Trail escape.

Big House by Expo Center, Airport, Churchill Downs

Perfect for large groups, with a MAIN HOUSE consisting of 3 bedrooms, as well as a CARRIAGE HOUSE with 2 bedrooms and an incredible GAME ROOM! Located in Beechmont, close to Churchill Downs, SDF Louisville Airport, Fair & Expo Center, University of Louisville, etc. There are smart TV’s in every room, two fully stocked kitchens, and modern bathrooms. The private courtyard between the houses includes a fire pit, a deck, and a paver patio with a gas grill, great for entertaining.

Bourbon Trail Villa|King Suite|Fenced Backyard|BBQ

⚜1900 sq-ft of modern living space ⚜1,000 sq-ft of fully fenced outdoor entertainment space ⚜Weber grill, wood burning fire pit (wood included), huge swivel umbrella and outdoor dining for 6 ⚜Fully stocked Chef's kitchen ⚜Dry Bar ⚜Big Screen TV's in every bedroom ⚜Netflix Included ⚜Games & books for kids and adults ⚜3rd story office space with twin bed and city skyline views ⚜Urban bourbon trail ⚜Pet friendly! ⚜Minutes from Churchill Downs, Distilleries, & KY Expo Center

4Bdrm ☑ Near Expo ☑ Downtown ☑ Spacious!

- 2.5 mi to Expo Center - 10 min drive to downtown (great access to the interstate) - 10 min drive to downtown distilleries - University of Louisville = 1.8 miles - 1.8 miles to the KY Derby • Spacious home for larger groups • Central Location, Easy Interstate Access • Fully Furnished + Linens and Towels + Stocked Kitchen • Parking for 4 cars • Quiet & safe neighborhood • Internet • Onsite washer + dryer No Locals No Parties (only registered guests)

☼ Family Friendly | Safe, Restful, Central ☼

We customized our residence to merge the practicality of family living with elegant aesthetics. As a young family ourselves, we understand the challenges of traveling with children and aim to create a vacation-like atmosphere for you. Our home is designed to keep the little ones entertained while providing you with some relaxation. Nestled in a tranquil residential area, our house is conveniently located less than 10 minutes from all major attractions.

Derby City Luxury Home: Best Location/Walk To All

Beautifully renovated, 4 bedrooms, 2.5 baths home centrally located on one of the few unique walking courts in the hip Highlands neighborhood. Steps away from some of the city's best restaurants and night life. Located just a few doors down from Bardstown Rd. This home has tons of charm and character with 9 stained glass windows. Fully renovated to provide modern luxury updates while maintaining the unique character of this 100 year old home.

The Castle Mint Highland House

Enjoy Louisville year-round from this beautiful Victorian home in a central, lively neighborhood. Stay cozy for a winter getaway, embrace spring energy, and experience the excitement of Derby season. Walk to Highlands bars and restaurants, with Downtown and Nulu just minutes away. Perfect for groups, the home offers multiple living and dining spaces, great beds, and stylish décor—providing comfort, space, and charm for a memorable stay.