Family-friendly vacation rentals in Highlands

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Highlands

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

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Guest favorite

A modern kitchen features dark cabinetry and a large island with seating for two. Natural light pours in through a window, illuminating the white subway tile backsplash and stainless steel appliances. Wooden ceiling beams add character to the airy space.

Apartment in Cherokee Triangle

4.94 out of 5 average rating, 297 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 favorite

A modern living area is depicted, featuring a white built-in shelf surrounding a gas fireplace. Above the fireplace, a flat-screen television displays various streaming options. The shelves are adorned with decorative items and storage baskets, adding organization to the space.

Condo in Highlands

4.93 out of 5 average rating, 207 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.

Guest favorite

The living area features two brown leather sofas arranged around a glass coffee table atop a light-colored area rug. Natural light floods in through multiple windows, dressed with sheer white curtains. A modern floor lamp stands beside one sofa, enhancing the inviting atmosphere.

Home in Germantown

4.89 out of 5 average rating, 107 reviews

Cozy 2nd-Floor Flat Near Downtown & Bourbon Trail

Discover Louisville's charm in this renovated brick building! Perfectly located near downtown, Paristown Hall, the airport, Expo Center, and trendy spots in Highlands and NuLu. Enjoy privacy with a private entrance, fenced in yard, self check-in and free parking. This place is perfect to relax after hitting the bourbon trail, exploring the city or any other event you’re in town for. The 2nd floor flat is a cozy retreat with well-appointed amenities to make your Louisville stay one to remember!

Top guest favorite

The exterior showcases a charming white house with large windows adorned with string lights, offering a glimpse of the interior space. A wooden deck extends out front, while a covered patio area is visible to the side, surrounded by lush greenery.

Cottage in Irish Hill

4.96 out of 5 average rating, 186 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 favorite

A modern living area features a soft pink sofa embellished with decorative floral pillows. A glass coffee table is centered on a multi-colored area rug. Light enters from large windows outfitted with sheer curtains, creating a bright and inviting space. Artwork adorns the nearby walls.

Home in Louisville

4.94 out of 5 average rating, 189 reviews

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

Guest favorite

A dining area is visible with a wooden table surrounded by six modern chairs. A soft, blue patterned rug covers the floor, complementing the natural light pouring in through large windows. A cozy living space can be seen in the background, featuring comfortable seating and greenery.

Apartment in Highlands

4.86 out of 5 average rating, 617 reviews

Walkable, 1920s bungalow in Historic Highlands

Beautifully renovated, 800 sq ft, 2 Bedroom, 1 bath apartment centrally located in the historic Highlands neighborhood. Small but efficient kitchen for staying in, and a coffee bar in the dining room, to get you moving. Excellent restaurants, coffee shops, and boutique shopping within a few blocks. Beautiful Cave Hill Cemetery, and Cherokee Park are nearby, as well as a playground and dog park just a block away. A Walgreens is just a few steps away for groceries, etc.

Top guest favorite

A unique hanging chair with plush cushions sits beside a glass coffee table. The table is adorned with orange dishware holding lit candles and crystals. Colorful reflections are cast across the room, highlighting the vibrant decor and inviting atmosphere.

Apartment in Louisville

4.96 out of 5 average rating, 140 reviews

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⚜️

Superhost

The living area features a comfortable sofa adorned with decorative cushions, set against a backdrop of large windows with colorful stained glass accents. A contemporary television is mounted on the wall, while a rustic coffee table sits atop an ornate area rug, accompanied by a cozy armchair.

Home in Highlands

4.89 out of 5 average rating, 140 reviews

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.

Top guest favorite

A charming balcony features a wooden table surrounded by four slatted chairs. A potted fern hangs gracefully from the angled ceiling, with views of lush greenery visible beyond the railing, creating a serene outdoor space.

Guesthouse in Tyler Park

4.98 out of 5 average rating, 300 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.

Superhost

A cozy seating area is showcased, featuring a modern orange armchair paired with a matching ottoman. A stylish floor lamp provides soft lighting, while a wooden shelf above displays books and decorative items. A textured blanket drapes over the chair, enhancing the inviting ambiance.

Apartment in Highlands

4.9 out of 5 average rating, 166 reviews

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.

Guest favorite

Apartment in Germantown

4.93 out of 5 average rating, 177 reviews

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!

Guest favorite

A modern kitchen features navy blue cabinetry paired with white tiled backsplashes. Stainless steel appliances, including an oven and microwave, are complemented by a gold faucet. A large window allows natural light, reflecting off the light countertops and showcasing the organized space.

Tiny home in Irish Hill

4.96 out of 5 average rating, 177 reviews

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!