Holiday rentals with a patio in Highlands

Modern stay for Derby minutes from Churchill Downs

Enjoy a stylishly 'Louisville' themed experience at this centrally-located home. Minutes from Churchill Downs, Downtown Louisville and the Highlands. STEPS from Logan Street market boasting local shopping, eateries and activities. This place has it all - comfort, style, space and amenities! 3 bedrooms (with TVs), a sleeper sofa & 2 full bathrooms. Full kitchen, chic living space and laundry room provide the perfect place for your Louisville stay! Spacious backyard and off street parking in rear!

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

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.

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.

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

Highlands Midcentury Getaway w/ Firepit & King Bed

Welcome to "Ruby"- the coolest, most conveniently located home in the city. From head to toe, Ruby is decked out with all the ingredients for a fun, relaxing Louisville stay. Occupying the first floor of a beautiful Victorian home, Ruby 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.

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

Historic Derby Carriage House

Historic Carriage House- 2 BR, 1.5 BA Oasis situated 10 mins to downtown, a 10 min walk to restaurants, shops, and groceries, and a 15 min drive to Churchill Downs. Right across the street from two parks and bike trails for a pleasant escape close to the bustle of Louisville nightlife. Free Parking, Wifi and Smart TV access accommodation as well as spa bathroom with soaking tub, jetted shower, and heated towel rack. Down the street from Cherokee Art Festival.

~The Vibe on Vine~ time to rest & relax

The Vibe is a charming retro haven with indoor/outdoor living in the heart of Louisville! This is a time capsule of old Louisville design combined with modern comforts, providing you with a unique and memorable stay! Dog friendly and located in the heart of Germantown, The Vibe is minutes from Bardstown rd, NULU, Baxter ave, breweries and the distilleries! Enjoy a movie night in the living room and dine on a converted bowling ally lane table in the kitchen!

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.

Location! Corner downtown condo!

Welcome to your stylish urban retreat in the heart of downtown Louisville! This studio corner unit condo boasts modern amenities and stunning city views through floor-to-ceiling windows. With an updated bathroom and kitchen, plus a location within walking distance to the KFC YUM Center, shops, and restaurants, this condo offers the perfect blend of comfort and convenience for your stay in Louisville. Book now and experience the best of Louisville living!

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.