Family-friendly vacation 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 favorite

Apartment in Louisville

4.94 out of 5 average rating, 232 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.

Aug 13 – 20

ﺩ.ﺇ550 per night

Superhost

Cottage in Louisville

4.85 out of 5 average rating, 264 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.

Oct 19 – 26

ﺩ.ﺇ451 per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 228 reviews

Highlands Haven Cottage

This luxurious and charming 1 bedroom home in the prime area of Louisville and The Highlands, is walking distance to the Douglass Loop area of shops and dinning, the Bardstown Rd corridor of shops and dinning and more starts at The Loop, as well as the locally famous Farmers Market on Saturday mornings! This 800 sf fully furnished home features 1 bedroom, 1 bath, a large & bright family room, and a fully outfitted kitchen, is literally minutes to lots of local amenities, dining, shopping, etc!

Nov 5 – 12

ﺩ.ﺇ484 per night

Guest favorite

Apartment in Louisville

4.99 out of 5 average rating, 136 reviews

Front Porch on Frankfort - So Clean - King Bed

So you feel safe, we still spray lots of disinfectant after cleaning. A short walk to unique restaurants, boutiques & galleries lining Frankfort Ave. Have a fun night on the town or relax on the front porch. People compliment us on our cleanliness, the comfy bed and overall cheery feeling while they visit our place. If you aren't enjoying the front porch , enjoy the cozy inside with the Roku TV, & bar. FYI, during Covid we kept long term tenants so we don't have as many recent reviews. 5 Stars!

Jul 26 – Aug 2

ﺩ.ﺇ430 per night

Guest favorite

Guesthouse in Louisville

4.93 out of 5 average rating, 284 reviews

Charming Carriage House with 2 private baths.

Our home and Carriage House in is an extremely nice, safe beautiful neighborhood. I know many guests including myself are even more concerned with cleanliness. Rob and I have always taken extreme pride in assuring our guest house is spotless. However, we have taken it up another notch. We have purchased a Utilizer that sanitizes areas with it's ultraviolet light. We use this machine after each guest to ensure the air and every surface is sanitized. It is truly home away from home!!!

Jul 25 – Aug 1

ﺩ.ﺇ401 per night

Guest favorite

Loft in Louisville

4.97 out of 5 average rating, 941 reviews

Derby City Loft - Free downtown parking!

If this loft is booked, please check out my other listings.. https://www.airbnb.com/h/bourbon-city-loft https://www.airbnb.com/h/river-city-loft Spacious 900 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!

Nov 27 – Dec 4

ﺩ.ﺇ498 per night

Guest favorite

Guesthouse in Louisville

4.98 out of 5 average rating, 245 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.

Oct 20 – 27

ﺩ.ﺇ393 per night

Guest favorite

Apartment in Highlands

4.93 out of 5 average rating, 160 reviews

Cozy Lg Studio Apt-Close to Food, Music, 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!

Jan 18 – 25

ﺩ.ﺇ393 per night

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 664 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. This newly constructed carriage house has all the amenities for any length of stay, including garage parking with room for bikes or kayaks. 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.

Aug 22 – 29

ﺩ.ﺇ318 per night

Guest favorite

Bungalow in Louisville

4.96 out of 5 average rating, 274 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!

Nov 12 – 19

ﺩ.ﺇ409 per night

Guest favorite

Guest suite in Louisville

4.86 out of 5 average rating, 313 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! :)

Oct 5 – 12

ﺩ.ﺇ329 per night

Guest favorite

Condo in East Market District

4.99 out of 5 average rating, 277 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.

Oct 17 – 22

ﺩ.ﺇ519 per night