Family-friendly holiday rentals in Original Highlands, Louisville

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Original Highlands, Louisville

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Cherokee Triangle

4.94 out of 5 average rating, 289 reviews

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.

Guest favourite

Cottage in Germantown

4.86 out of 5 average rating, 319 reviews

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.

Top Guest favourite

Apartment in Germantown

4.93 out of 5 average rating, 125 reviews

Vintage yet Modern Highlands home! Walk to venues!

Spacious 1st floor apartment in a Victorian duplex home in the heart of the Highlands/Germantown. We are ready to host for short, mid & long term! Because of our close proximity to Louisville’s vibrant nightlife, eclectic dining scene & shopping it’s no wonder visitors flock here to get a taste of something amazing! Perfect place for your Ky Derby home base! Walk down to the hottest Arts & Music venue in town- Old Forester Paristown Hall! Don’t forget about the Bourbon tours and new breweries!

Guest favourite

Condo in Original Highlands

4.93 out of 5 average rating, 201 reviews

Large Townhouse, Walk to All! King beds, 2.5 baths

Large, 3 story townhouse sleeps 6 in 1600 sq. ft. Step out the door to best walking neighborhood in Louisville. Great coffee shop 150 ft. away, with a dozen places to eat, from fancy to casual, within the block. Parks, movies, live music are 10 minute walk or less away. 2 King bedrooms, each with full bath, 1 queen and 1 twin daybed w/ trundle. Fully equipped kitchen, 3 large smart tvs, wifi and cable! Kitchen fully equipped, from quality appliances to pots/pans/plates/cutlery/glasses/etc.

Top Guest favourite

Cottage in Louisville

4.96 out of 5 average rating, 184 reviews

ArTisTs CoTTaGe

Enjoy peaceful privacy with center city convenience! Bright, open ambiance. Art and music supplies, books, toys, games, CD's, movies. Two decks and a covered patio. Found art gardens and galleries. Fully equipped kitchen with granite counters. Large windows in downstairs bedroom with queen bed and gas fireplace. Ladder access to queen bed in skylit loft. A perfect getaway for artists/writers on retreat, solo adventurers, couples, business travelers and small families with well behaved kids.

Top Guest favourite

Guesthouse in Tyler Park

4.98 out of 5 average rating, 295 reviews

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.

Top Guest favourite

Guesthouse in Germantown

4.96 out of 5 average rating, 773 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. The carriage house has all the amenities for any length of stay, including garage parking with room for bikes. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

Top Guest favourite

Bungalow in Germantown

4.96 out of 5 average rating, 316 reviews

Charming Bourbon Bungalow - 1 Mile from Downtown!

You will love this quaint Germantown house located 2 miles from almost anywhere you would want to be in the city! Two bedrooms and one bath await you, along with a full kitchen, large living space, and spacious back yard. Close to many great restaurants, downtown attractions, the Highlands, Churchill Downs, the riverfront, and many great parks. Don't wait--book now!

Guest favourite

Apartment in Cherokee Triangle

4.93 out of 5 average rating, 269 reviews

The Highlands Original Condo

Our brand new renovated 1BR condo is located in a famous Highlands' neighborhood. Conveniently located about 5-8 minutes from Churchill Downs, KFC Yum Center, Cardinal Stadium, Convention Center, Center for the Arts, Downtown Distilleries, NuLu&Germantown areas, 12 minus from the airport. Walking distance to many great restaurants, bars, shops, and parks.

Top Guest favourite

Home in Clifton Heights

4.97 out of 5 average rating, 231 reviews

Charming Shotgun Style Home, Great Location

This updated shotgun house is thoughtfully decorated with hints of handcrafted detail. Outdoor spaces include a front porch and a private patio. Cozy with a modern vibe. It can sleep up to 6. An ideal choice for couples, families, or a getaway with friends. Perfect for The Kentucky Derby and all Louisville has to offer.

Guest favourite

Apartment in Deer Park

4.91 out of 5 average rating, 535 reviews

Studio in the Highlands

The Studio next to The Studio is a beautiful, recently renovated apartment located in the Highlands of Louisville. The space is located next to a working photography studio and is centrally located to all of Louisville's great attractions. Walk to some of our best restaurants, unique shops, and fantastic nightlife.

Guest favourite

Home in Original Highlands

4.94 out of 5 average rating, 127 reviews

Barret House, prime location, walk to everything!

Fully furnished luxury duplex, 3 bedrooms (recently added king, and also two queen beds) and 2 full baths, 2 chefs kitchens, with hide-a-bed and futon in second floor common area; This rehab has been designer decorated with a huge living area, it close to some of the finest restaurants in town. *No locals, please*