Family-friendly vacation rentals in Original Highlands, Louisville

4.94 out of 5 average rating, 286 reviews

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 Louisville

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.

4.86 out of 5 average rating, 317 reviews

A bright living room is furnished with a gray sofa and two blue armchairs. A glass coffee table is centered on a colorful area rug. A flat-screen TV sits on a wooden console, and a bookshelf is visible, filled with various books. Natural light enters through multiple windows.

Cottage in Germantown

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.

Apartment in Original Highlands

4.93 out of 5 average rating, 122 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!

4.96 out of 5 average rating, 182 reviews

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 Louisville

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.

Apartment in Old Louisville

A private garden area features a small pond surrounded by lush greenery and colorful flowers. Various seating options, including chairs and benches, are arranged throughout, offering spaces for relaxation. Potted plants add vibrant touches to the serene outdoor setting.

4.91 out of 5 average rating, 321 reviews

Charming Apartment in Historic Old Louisville

Beautiful, clean, sunny, private apartment with private entrance and garden space. No cleaning fees or any other fees not charged by Airbnb ! Sleep machine provided to help with good nights sleep! Located in beautiful historic Old Louisville, one of the largest contained Victorian neighborhoods in the country. Near historic Churchill Downs and just moments away from fantastic restaurants, and other attractions. A short Uber, Lyft or Taxi ride to almost anywhere in the downtown area.

Loft in Central Business District

A spacious bedroom features a king-size bed with striped bedding, complemented by an orange accent pillow. The exposed brick wall adds character, while a small nightstand with a lamp sits alongside. Natural light filters through the window, illuminating the warm wood flooring.

4.97 out of 5 average rating, 834 reviews

Bourbon City Loft - Free downtown parking!

If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

4.98 out of 5 average rating, 292 reviews

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 Louisville

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.

4.96 out of 5 average rating, 766 reviews

A cozy sitting area is furnished with two slender armchairs and a small ottoman, placed on a decorative rug. A flat-screen TV is mounted on the wall, and a narrow table holds decorative items. Sliding doors lead into the bedroom, enhancing the open feel.

Guesthouse in Germantown

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.

4.96 out of 5 average rating, 314 reviews

A spacious kitchen area features wooden cabinetry and modern appliances, including a stove and microwave. A brick column adds a rustic charm to the room. A round table with four barrel-style chairs is positioned underneath a wall clock, enhancing the inviting atmosphere. Artwork of a horse is displayed above a counter.

Bungalow in Germantown

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!

4.93 out of 5 average rating, 265 reviews

A bright living area features a gray sofa centered on a patterned area rug, complemented by two armchairs. A large bookshelf filled with books occupies one wall, while natural light streams through the windows, highlighting the warm wood floors and modern decor.

Apartment in Louisville

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.

Guest suite in Louisville

The exterior of a charming three-story home is framed by lush greenery and mature trees. A spacious porch with steps leads to the main entrance, while the surrounding garden is covered in vibrant foliage, contributing to a welcoming neighborhood atmosphere.

4.85 out of 5 average rating, 360 reviews

Basement Abode in Cherokee Park

At our one bedroom (king bed) basement abode you will have your own private entrance in the back of the main home in the Historic Cherokee Park neighborhood. Quiet and secure with a location that simply cannot be beat. Plan on parking your car and walking to the best park, restaurants, local shops and bars in Louisville. We are dog friendly! :)

Condo in East Market District

The living area features a combination of seating options, including two patterned chairs and a black leather sofa. A glass coffee table sits on a light area rug, while a television is positioned against the wall. Natural light enters through a window, with dining chairs set nearby.

4.99 out of 5 average rating, 315 reviews

Louisville's Best Neighborhood Gallery Square NuLu

One bedroom contemporary condo with plenty of amenities including TV in bedroom and living room, fully furnished kitchen, washer/dryer, ironing board, walk-in closet and secured parking for one vehicle. Located in the trendy NuLu area of downtown Louisville with bars, shops and numerous restaurants that are just minutes away from the front door.

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Popular amenities for Original Highlands, Louisville family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 160 reviews

Southern Comfort-Hottub wlk 2 Resturant Row & Shop

HaydenRating, 5 stars1 month ago

Within walking distance of several restaurants and a quick drive to a lot of greats bars and other things to do.

Superhost

A coffee station features a Keurig machine alongside a selection of coffee pods and snacks, arranged in a woven basket. Behind, a dining area is visible through large windows, inviting natural light into the space.

4.97 out of 5 average rating, 29 reviews

2.0 Southern Comfort Highlands-Cherokee Triangle

RyaneRating, 5 stars8 months ago

One of the best Airbnb’s I’ve stayed in! Lots of extra little amenities, the decor was unique and well thought out, and the location was perfect. We travel to the area often and would definitely book again.

A private hot tub is situated on a paved area, surrounded by a wooden fence for added privacy. Colorful flower pots with blooming flowers are positioned nearby, complementing the fresh green grass. Two red chairs sit in the backyard, inviting relaxation.

4.99 out of 5 average rating, 249 reviews

NEW Hot Tub, Walk 2 Park, Whole Foods, Movies Mall

ChristiRating, 5 stars3 weeks ago

We loved staying at Kristen’s place. Spacious and quite lovely. We will definitely stay again in the future. Many restaurants nearby. Beautiful neighborhood.

A grand two-story brick home is showcased, featuring multiple peaked roofs and expansive windows. Symmetrical landscaping adds to the curb appeal, with neatly trimmed shrubs and a manicured lawn. A wide pathway leads to the front door, framed by steps and elegant railings.

Home in Fern Creek

4.67 out of 5 average rating, 51 reviews

All You Need and More!

BradRating, 5 stars2 months ago

This house is in a very nice neighborhood with plenty of restaurants and shopping nearby. There's plenty of room for a big family/group. I had another Airbnb host cancel my reservation only 2hr before check in. I was already on the highway with my family and Barksdale management moved this property up on their cleaning list as it had just been vacated around noon in order to accommodate us. I can't say enough for how much we appreciated that. Thank you so much for saving our weekend!!!

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Family- and pet-friendly home rentals

4.86 out of 5 average rating, 170 reviews

A charming cottage is set on a spacious lawn, framed by manicured shrubs and trees. The exterior features a traditional design with white siding and dark shutters. A gravel driveway leads to the home, providing ample parking space.

Cottage in Prospect

Cottage in Louisville,KY on Scenic River Rd

LauraRating, 5 stars2 weeks ago

Very comfortable home close to everything. Would definitely stay here again.

Home in Central Business District

A charming red brick building exhibits a vibrant yellow entrance, flanked by manicured greenery and trees. Large windows invite natural light, while a wrought-iron fence surrounds the inviting front yard, completing the home’s welcoming exterior.

4.83 out of 5 average rating, 217 reviews

NULU - Walkable, Spacious & loads of personality!

DavidRating, 5 stars1 week ago

Great location. Lots of room for families or couples. Peaceful back patio, etc

Townhouse in Original Highlands

A modern living area features a large flat-screen television mounted above a gas fireplace. Comfortable seating includes a sofa and an armchair, while a glass coffee table rests on a patterned rug. Natural light enters through two windows beside the front door.

4.96 out of 5 average rating, 136 reviews

Restaurant Row Townhouse

ChristiRating, 5 stars1 month ago

Deidre’s place was outstanding! We never had to get back in our car because everything was walking distance! We played the sound machine at night and slept like a rock!! Everything was great. I’d 100% recommend this place! We’re hoping to return this summer.

Superhost

A cozy library area features two plush armchairs facing a dark wood bookshelf filled with books. Artwork adorns the walls, and natural light filters in through the two windows, creating a warm and inviting reading space.

Home in New Albany

4.95 out of 5 average rating, 196 reviews

Spacious Historic Home, Louisville Adjacent

LilyRating, 5 stars1 month ago

I stayed at Benjamin’s place for the Derby this year with friends, and we had an amazing time! The house is beautiful and so well decorated. It was perfect and one of my favorite Airbnb’s I’ve stayed in. Thank you so much, Benjamin! We will be back :) also loved how dog friendly it was - our 2 small poodles had the time of their life!

4.98 out of 5 average rating, 179 reviews

The inviting front porch features two chairs with colorful cushions positioned on a small area rug. A potted plant adds greenery to the space, while the entrance is framed by a vibrant red door and white columns, providing a welcoming atmosphere.

Townhouse in Louisville

Charming 2 BR home by Emerson Park & Gardens - UL,

SaraRating, 5 stars1 month ago

We really enjoyed our stay! This place is FANTASTIC! The interior is really, really well done - very clean, comfortable and inviting. Loved the tall ceilings, great master bath shower, and large well-appointed kitchen. Also enjoyed sitting on the porches - both front and back, and the fenced yard was great for our dog. Very nice neighbors. Thank you so much for a wonderful stay in Louisville!

4.89 out of 5 average rating, 192 reviews

A wooden sign is displayed on a wall, featuring the text 'Welcome to Our Nest' in an elegant cursive font. The sign has a rustic design with a whitewashed finish, and a pink ribbon is tied at the top for hanging.

Loft in Crestwood

Welcome to the Nest!

ChristinaRating, 5 stars1 week ago

The place was clean, easy to find, and dog-friendly which was great for our pup!

A spacious living area features large windows allowing natural light to fill the room. A comfortable couch and a reclined chair offer seating, with a coffee table in front. A fireplace serves as a focal point, framed by decorative elements and bookshelves.

4.96 out of 5 average rating, 267 reviews

Home near the Highways

RandolphRating, 5 stars1 week ago

We had a great experience, Ross was an excellent host. He was friendly, easy to communicate with and helpful. His house was very clean full of amenities and was very easy to find. I would definitely recommend this cozy inviting house to anyone.

Guesthouse in Crescent Hill

A white, two-story wall is complemented by a wooden deck featuring a railing. Flower pots are placed at each end of the deck, and large windows are visible on the upper level. A staircase leads from the ground level to the deck.

4.9 out of 5 average rating, 135 reviews

Cottage Park Carriage House. Rest w/Hollyhock

William LoriRating, 5 stars2 weeks ago

Wonderful accommodations with many generous amenities, including a little coffee bar with lots of coffees, many spices for cooking, and everything you need in the bathroom, including body wash, shampoo, conditioner, and hairdryer. A perfect accommodation for those who love to travel light. The apartment is in a lovely neighborhood and has its own private entrance, up some outside stairs. It was clean and spacious. Thanks for a wonderful stay. We can’t wait to return.

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Family-friendly home rentals with a pool

A comfortable living room is presented with deep blue walls and large windows, allowing natural light to fill the space. Two sofas and several accent chairs are arranged around a wooden coffee table, with decorative pillows adding color. Vibrant artwork adorns the walls.

4.98 out of 5 average rating, 162 reviews

KY Derby, Bardstown Road, Brewery, 2Decks w Porch

EmileeRating, 5 stars3 weeks ago

Louisville exceeded our expectations and so did this home! Extremely spacious and well stocked for four adults and kids under 8. Lots of bathrooms and the beds were super comfy. Huge yard too! We’d definitely stay again!!

Guest suite in Louisville

A heated saltwater swimming pool is surrounded by a concrete patio and lush greenery. The area features a spacious cabana with seating, a chaise lounge, and colorful pool floats. Nearby, a small garden and manicured lawn enhance the outdoor setting.

4.96 out of 5 average rating, 372 reviews

Cherokee Park Oasis with Private Entrance

TaylorRating, 5 stars1 month ago

Beautiful place - even better than the photos! The backyard is so peaceful and we enjoyed a dip in the pool. The 2 bedrooms and common area were very spacious and great accommodations for my family of 4. Keegan was very helpful leading up to and during our stay.

Guest suite in Jeffersonville

An inviting backyard area showcases a glistening pool surrounded by palm trees and vibrant lounge chairs. A gazebo can be seen in the background, with a round table and chairs set in the foreground, creating a perfect space for outdoor relaxation.

4.93 out of 5 average rating, 182 reviews

Come Explore Jeffersonville & Louisville

MichelleRating, 5 stars1 month ago

Loved everything about this spot, especially having use of the pool and hot tub! My kids loved the theatre room. We will definitely stay again.

A spacious backyard is illuminated by string lights at dusk, featuring a hot tub and multiple seating areas around a fire pit. The well-maintained lawn and patio area create a welcoming outdoor space for relaxation and gatherings.

4.97 out of 5 average rating, 248 reviews

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

BrianRating, 5 stars1 month ago

This house is absolutely fantastic. Super clean, super comfortable. The beds and pillows are amazing. I would highly recommend this house for any gathering. We were a group of four men doing bourbon trail related things, and relaxing at night next to the fire pit and in the hot tub.

An open living space features a comfortable sofa and a coffee table, complemented by a dining area with a circular table for six. A kitchen island with seating for three is present, along with a gas fireplace set into a stone wall, adding a cozy element.

4.97 out of 5 average rating, 34 reviews

Highlands Oasis- Summer and Winter Retreat

JacksonRating, 5 stars2 months ago

A wonderful home hosted by wonderful people. I can’t thank Amy and Carol enough for being incredible hosts and opening their home to us. Would certainly recommend this to anyone considering staying in the area!

4.91 out of 5 average rating, 153 reviews

Sleeps 16, Heated Pool , Hot tub, Close to Dwtn

VictoriaRating, 5 stars3 weeks ago

Niloo’s place was great for our weekend bachelorette party. The house was exactly like the pictures and very clean. Having the pool was a nice addition during the day as well! Niloo was very responsive and made sure everything was set for our arrival. I would definitely recommend staying here.