Family-friendly 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.

Walk to everything • Quiet, Private, and Cozy

Tucked along a quiet, tree-lined street in Louisville’s Original Highlands neighborhood, you’ll find a cozy, private retreat filled with character and unique decor. Featuring a large master bedroom with king Sleep Number bed, a spacious living/dining room area, 2 full bathrooms, and a cozy full sized guest room. Walk to the best restaurants, boutiques, and coffee shops. Explore the nearby parks or unwind in your peaceful, historic hideaway. 1 mile from NULU 2 from downtown 5 from the Downs

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

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

Velo Studio Flat / Paristown / Highlands /

Next to the The Highlands, this bike friendly house is in Paristown with great restaurants, Louisville Stoneware & an easy walk to Baxter & Bardstown Rd for nightlife. A clean, comfortable & stylish home in a quiet area. Five bicycles to access scenery nearby with a relaxing screened porch to unwind. Perfect for athletes, couples, families or business travelers. Cherokee Park is close with plenty of woods with trails for biking & hiking. Downtown, Big 4 Bridge & waterfront just 2 mi.

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.

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.

The Marie Airstream at Progress Park in Derby City

Marie is a 1996 Excella, perfect for groups, families, or midweek getaways.Skip the packing & extra costs - everything you need is already here. Maire combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Cozy studio near music hall, food stops and 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!*

Trendy Tiny Home w/ King Bed Loft

Unique experience in style! Enjoy a weekend or an extended stay at this charming carriage house just walking distance to popular restaurants, breweries and local shops. The location is perfect! Inside you'll find a fully equipped kitchen, bathroom, living room with a 55" smart tv, a dedicated work space/desk and a king sized bed in the loft. Guests will have privacy with self-check in smart locks and a dedicated parking space. We can't wait to host you!

Sun-filled Phoenix Hill Studio

Located in the Phoenix Hill neighborhood, it's a short 11 minute walk to East Market District restaurants and attractions or a 15 minute walk to Gravely and other Original Highlands destinations. 11 minute drive to Churchill Downs 5 minute drive to the Highlands 4 minute drive to East Market restaurants and shopping. Ample Lyft and Uber drivers in this neighborhood to take you anywhere you want to go. .