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.

0 of 0 items showing

1 of 3 pages

Guest favorite

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

4.86 out of 5 average rating, 314 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.

Guest favorite

A charming exterior of a renovated shotgun-style home is showcased, featuring a light-colored façade and decorative blue shutters. A small front porch invites visitors, with a neatly maintained garden bed displaying colorful flowers and a fenced yard providing privacy.

Home in Louisville

4.95 out of 5 average rating, 244 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!

Superhost

A living area is presented with a stone fireplace as a focal point, topped by a flat-screen television. Natural light filters through two windows, complemented by a leafy indoor plant. Cozy seating includes a bright yellow armchair and a textured green throw pillow.

Home in Crescent Hill

4.79 out of 5 average rating, 154 reviews

The Hillcrest- Great Crescent Hill Location!

Great space in Crescent Hill part of Louisville. Easy access to downtown, Expressway University of Louisville & Waterfront Park areas. Walking distance to Bars & Restaurants on Frankfort with shopping in the area. The space is furnished clean and minimalistic, vintage themed. Great for families or friends all getting together. Three nice sized bedrooms. One full bathroom upstairs and a half bathroom downstairs in basement. Main floor has a dining room seating 8, kitchen & living room.

Top guest favorite

A cozy living room features two black leather armchairs adorned with blue accent pillows. A round coffee table with a glass top sits on a colorful patterned rug. A modern television is mounted above a black fireplace, flanked by built-in shelves filled with books.

Home in Louisville

4.92 out of 5 average rating, 123 reviews

5 bedroom/4 bath Walk to All, Historic Highlands

4 traditional bedrooms (5th convertible den/bedroom), 4 bath with great deck, porch and patio. 2 king bedrooms, 2 queen bedrooms, 1 queen sleeper and den double sleeper. Fabulous 3rd floor primary suite, updated baths, stylish mod kitchen. Beautifully remodeled 2500 sq. ft. house in Cherokee Triangle, walk to everything- restaurants, parks, cafes, shops! Just 1/2 block off Bardstown Road and 1 block from Cherokee Park. Walk to dozens of restaurants, shops, café, theatres and two great parks.

Guest favorite

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.

Home in Central Business District

4.83 out of 5 average rating, 211 reviews

615 E Washington, Nulu Bourbon Trail

RECENTLY MADE AVAILABLE FOR DERBY 2025 - Ask about Specials NULU/Downtown Urban & eclectic downtown home 1/2 BLOCK to ANGELS ENVY BOURBON DISTILLERY & SLUGGER FIELD!! 3,000 square feet of living space 1,500 sq ft patio -High-end kitchen with chef-ready appliances -Dining room and wet bar room for congregating with friends -2.25 bathrooms rival high end hotels -Bedrooms with plush memory foam mattresses and linens. -Experience is completed w SONOS to enjoy whole home sounds.

Top guest favorite

Home in Elizabeth

4.98 out of 5 average rating, 129 reviews

Cabin on Lake Close to Louisville Ky

Welcome to Little Cedar Lodge, our little slice of heaven near the town of Elizabeth, Indiana. Enjoy the peace and solitude overlooking the quiet private lake (wake speed only), yet close to Caesar’s Casino, golf, wineries, and the city of Louisville with all its activities and nightlife. Great for a romantic getaway for two, or for your entire family. It would also be great for a small church or business retreat. We can accommodate up to 10 if you double up in some beds.

Top guest favorite

A cozy living area features a brown sectional sofa and a wooden coffee table on a striped rug. A tall lamp provides soft lighting, while built-in shelves display decorative items. Light enters through shuttered windows, enhancing the room's inviting ambiance.

Cottage in Prospect

4.86 out of 5 average rating, 165 reviews

Cottage in Louisville,KY on Scenic River Rd

My place is close to Downtown Louisville (7 miles along scenic River Road), restaurants (Captain's Quarters Riverside Grille, Pine Room, Blackstone Grill, Gustavo’s, Prospect Village Shopping Center 1 mile (grocery, pharmacy, Starbucks, fast food, dry cleaning), Farmer's Market, marina, liquor store, expressways (20 minutes to airport). You’ll love my place because of the views & location.

Top guest favorite

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

4.96 out of 5 average rating, 310 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!

Top guest favorite

A large black barn sits prominently in the image, complemented by lush green trees and shrubs. A gravel path leads towards the entrance, which is framed by manicured grass. The expansive farmland stretches into the background, under a clear blue sky.

Farm stay in La Grange

4.95 out of 5 average rating, 699 reviews

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

Guest favorite

An open living area features a gray sofa and two armchairs surrounding a coffee table set on a decorative rug. Light streams through the three windows, illuminating the wood flooring. A dining table is set to the side, and kitchen appliances are visible in the background.

Apartment in Louisville

4.93 out of 5 average rating, 261 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 favorite

A welcoming living area is highlighted by soft green walls and hardwood floors. A round table with a flower arrangement sits at the center, surrounded by a cozy sofa and a lounge chair. A television is positioned on a shelf, with doorways leading to other rooms.

Home in Louisville

4.96 out of 5 average rating, 222 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 favorite

A living area features a beige sofa adorned with teal cushions, paired with a blue accent chair. A small coffee table sits in front, complemented by a decorative plant and a magazine. The wall displays a framed artwork above a section of exposed brick.

Home in Highlands

4.92 out of 5 average rating, 230 reviews

Make us an offer we can't refuse Derby Weekend!

DERBY DEAL! MAKE US AN OFFER WE CAN'T REFUSE! Welcome to this well appointed, recently remodeled house in a prime location in the heart of Highlands with restaurants, bars, coffee shops and shopping, all within a couple of minutes walk. Churchill Downs is a short 10 minute drive, and Downtown is a couple of minutes drive.