Apartment 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.

Stylish groovy condo minutes from Churchill Downs

Welcome to Groovy Louis, a funky and eclectic condo in Louisville’s vibrant NuLu district. Sleeping up to 4 guests, this stylish retreat is just a short walk from Whiskey Row, the Louisville Slugger Museum, UofL, and a quick ride to Churchill Downs. Explore art galleries, antique shops, specialty stores, and one of the city’s top culinary scenes right outside your door. With modern amenities and unique charm, Groovy Louis offers the perfect blend of comfort, culture, and convenience. Book now!

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 Zen Oasis • Comfy, Clean & Cozy

Awesome Sweet Spot of a Louisville Location! This PRIVATE APT. with SELF CHECK IN + FREE PARKING is in a beautiful, safe neighborhood in the historic Highlands. Quick 2-min walk to magnificent Cherokee Park OR charming Bardstown Road - a multitude of eclectic galleries, bars, restaurants & shops to explore! Conveniently (5-10 min) located to Churchill Downs, Downtown Louisville, Louisville Seminary, NuLu, UofL, Bellarmine, Fair & Expo Center, Yum Center, Waterfront & the Airport⚜️

Basement Apartment in Germantown

Come stay in our rustic studio apartment with driveway parking in Schnitzelburg/Germantown, home to Monnik Beer Company, Nachbar, the Merryweather, and the Post. We’ve brought a little of our old home in East Tennessee to our new home in Louisville. This guest space features reclaimed wood from a barn Perry took down in Seymour, TN.; a stock tank shower; a refurbished farmhouse sink; a tobacco stake star wall hanging; and some Yee-haw Industries prints, straight from Knoxville.

The Bardstown-Louisville Nightlife

This spacious unit provides a front row seat to watch and experience Louisville from the comfort of your own private retreat in the middle of the best street in Louisville. Feet from many restaurant , bars and boutiques. During your stay spend time walking the neighborhood filled with boutiques, restaurants, bars, distilleries and art galleries. Start the bourbon trail or walk to the famous Cave Hills Cemetery. Private gatherings are allowed but house rules must be followed.

Cozy and Quiet in Schnitzelburg

This quiet one bedroom apartment is a great home base for exploring the Derby city! Separate entrance through a charming backyard/English-style garden. Less than 2 1/2 miles to historic Churchill Downs, less than a mile to Nord's famous bakery, Sunergos Coffee, Monnick Beer Company, Check's Bar & Grill, The Post and more. A short drive to the local restaurants and unique shops of Bardstown Road, NuLu and Frankfort Avenue. No Louisville locals can stay at this location.

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.

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!*

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.

The Point at Story and Frankfort Avenue

The Point is a spacious and completely renovated one bedroom (king) apartment. You will absolutely love the huge sectional couch while watching your favorite shows on the 65" smart TV. Unit very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.