Family-friendly vacation rentals in Saint Matthews

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Saint Matthews

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

R2,832 ZAR 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!

Jan 18 – 25

R2,491 ZAR 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

R2,213 ZAR per night

Guest favorite

Apartment in Louisville

4.98 out of 5 average rating, 250 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Feb 11 – 18

R2,105 ZAR 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!!!

Aug 25 – Sep 1

R1,843 ZAR per night

Guest favorite

Guesthouse in Louisville

4.98 out of 5 average rating, 243 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.

Aug 28 – Sep 4

R2,025 ZAR 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

R1,638 ZAR per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 112 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Oct 20 – 27

R2,298 ZAR per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 289 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Sep 11 – 18

R2,153 ZAR per night

Guest favorite

Loft in Louisville

4.83 out of 5 average rating, 471 reviews

Carriage House Loft

Come enjoy our Carriage House loft located in the popular Louisville neighborhood of Crescent Hill. The loft is equipped with wifi internet, TV, and kitchen supplies. You will be within walking distance to some of the most popular establishments in Louisville; including Blue Dog Bakery, Clifton Coffee, and the Parlour Pizza. Short Term License # LIC-STL-24-00014

Aug 19 – 26

R1,541 ZAR per night

Guest favorite

Home in Louisville

4.97 out of 5 average rating, 297 reviews

The Highlands Condo/Roof Deck

Our brand new renovated 1 BR 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 area, 12 minutes from the airport. Walking distance to many great restaurants, bars, shops , and parks.

Sep 9 – 16

R2,025 ZAR 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! :)

Jun 11 – 18

R1,781 ZAR per night