
Family-friendly holiday rentals in St Matthews
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in St Matthews
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Carriage House - Crescent Hill (Frankfort Avenue)
Newly constructed carriage house in a charming historic community. Enjoy your own private getaway in the heart of Louisville's Crescent Hill neighborhood. This carriage house features an open kitchen / living concept with two private bedrooms (each has a comfortable queen bed) and a shared bathroom. In close proximity to local shops, restaurants, coffee shops and parks. Located less than 5 miles from downtown Louisville, less than 6 miles from the Expo center, less than 7 miles from the airport

Swanky Fully Equipped St. Matthews Apartment
Swanky East End Private Apartment. Completely renovated in 2018. New Shower, fully equipped kitchen. Huge walk in closest, FlatScreen TV and WIFI all included. Party Deck and Spaceous Living Room are ready for your Visit. King Bed and Queen Sleeper Sofa with spacious living, await up to 4 guests. Great venue for Trinity Football, University of Louisville Sporting events, Churchill Downs, or simply hitting the Bourbon Trail. 10 min. Uber to Whiskey Row and Distillery And/or and Nulu District

The Sweet Spot! - Live Like a Local
Live like a local in one of Louisvilleās most sought-after neighborhoods, young professionals and families alike. Rich in history and surrounded by wall-to-wall dining, shopping, and entertainment, this vibrant area is known for its charm, energy, and premium appeal. Originally built as a single condo over two decades ago, the owner later acquired the neighboring unit and completely reimagined the entire second level. The result is a thoughtfully crafted space that truly feels like a retreat.

Hide away close to everything
Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Historic Cabin by Bourbon Trail
Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

The Dotti Airstream @ Progress Park in Derby City
Dotti is 16ft Bambi Airstream & sleeps 2 adults. Everything you need is already here. Enjoy your own private space PLUS access to boating, games, & more, all included with your stay. Dotti is our smallest offering, but has TONS of charm. Including a large covered patio with a swing bed! Please note Dotti does not have hot water. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

The River's Edge Oasis, close to downtown
Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

3 bedroom Crescent Hill cottage
Located on a wide, tree-lined avenue, this comfortable, stylish, and well-appointed Dutch Colonial is only a few minutes drive from Louisville's most popular entertainment districts, restaurants, and boutique shops along Frankfort Ave, Bardstown Rd, NULU and Downtown. Guests will enjoy the surroundings of one of Louisville's most desirable neighborhoods with Whitehall and Boyce College within walking distance and Garden Court, as well as historic Cherokee Park just a short drive away!

Exclusive one-story retreat close to attractions!
Discover this inviting apartment located in the heart of Louisville. Perfect for families or small groups, this thoughtfully equipped home comfortably sleeps up to 7 guests with two queen beds and a sofa bed. Enjoy the convenience of a fully equipped kitchen, flat-screen TVs, and reliable high-speed WiFi. With comfortable living spaces, dedicated parking, and proximity to local attractions, this charming retreat offers an ideal blend of comfort and convenience for your next stay.

Seneca View
700 ft² (70m²) of Open, light & airy space with modern amenities. Plz, NO smoking, toking , vaping, or any drug/cigarette use in/on property-- $300 fine. Convenient location in a quiet, sought-after neighborhood, yet within a few minutes of a bustling, busy Bardstown Road with many places to eat, shop and browse. Easy access from all major interstates: I-71, I-65 and I-64. Come stay for a week, on business (work desk is set up), or use for a fun, getaway weekend.

Hidden GEM, newly furnished in a safe, great area
Our āunitā is a great place to stay. Absolutely wonderful neighborhood with beautiful historic setting, cozy, safe and quiet. Short walking distance to many restaurants, shops, coffee houses. Majestic trees line properties and homes. Downtown & NULU 4 miles. Churchill Downs 10 miles, University of Louisville is 13 miles away. Golf & swim center .25 miles this. property is duplex. Very separate accommodations! Private!

St. Matthews Gem *Pinball *Private Parking
Welcome to your home away from home! This charming 2-bedroom house is located on our property but offers private access and private fenced area. The house features a pinball machine, board games, a Nintendo Switch, and an Xboxāperfect for relaxing after a day of exploring Louisville. Tucked away on a quiet dead-end street, this home offers private driveway parking and convenient highway access.
Popular amenities for St Matthews family-friendly rentals
Family-friendly home rentals with a hot tub

Cherokee Park Oasis with Pool and Hot Tub

Butchertown & NuLu's Shantyboathouse

Walking Bridge, Putt Putt House

Bourbon Trail*Tesla EV charging* HOT TUB

The Squirrel's Nest - 3 bed/2 bath with hot tub

Bourbon Trail Spacious Backyard NEW HotTub Grill!

Book now for Abbey Road on the River

4th Street Suites - Serene King Bed Suite
Family- and pet-friendly home rentals

Walk to Bourbon Trail | NULU Gem | Gated Parking

Colonel Lou Lou's

2BR Home Near Zoo & Fairgrounds ā Family-Friendly!

Cherokee Park Hideaway

The Caldwell Highlands/Germantown

Thompson Hideaway

Historic Home in a Walkable & Central Location!

Full House near EXPO Center - Best Location in Lou
Family-friendly home rentals with a pool

The Getaway!

Best view of the lake two bed two bath cottage #4

5BR w/ 6 King Beds + Hot Tub

Top 1%⢠Yard + Porch ⢠3BR ⢠Peppermint Cottage

Luxury Retreat with Hot Tub

Stylish DT Apt ⢠King Bed, Gym, Pool + Hot Tub

Lake Livin' & Bourbon Sippin'

Cozy City Condo in Norton Commons
When is the best time to visit St Matthews?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $224 SGD | $242 SGD | $249 SGD | $286 SGD | $415 SGD | $249 SGD | $267 SGD | $205 SGD | $320 SGD | $249 SGD | $240 SGD | $243 SGD |
| Avg. temp | 2°C | 4°C | 9°C | 15°C | 20°C | 25°C | 27°C | 26°C | 22°C | 16°C | 9°C | 4°C |
Quick stats about holiday rentals that are family-friendly in St Matthews

Total holiday rentals
Explore 150 holiday rentals in St Matthews

Nightly prices starting at
St Matthews holiday rentals start at $38Ā SGD per night before taxes and fees

Verified guest reviews
Over 2,920 verified reviews to help you choose

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
140 of St Matthews holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across St Matthews rentals

4.9 Average rating
St Matthews stays are highly rated by guests ā averaging 4.9 out of 5!
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- Rentals with breakfastĀ St Matthews
- Rentals with a firepitĀ St Matthews
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- House rentalsĀ St Matthews
- Rentals with a washing machine and dryerĀ St Matthews
- Pet-friendly rentalsĀ St Matthews
- Flat rentalsĀ St Matthews
- Rentals with a fireplaceĀ St Matthews
- Family-friendly rentalsĀ Jefferson County
- Family-friendly rentalsĀ Kentucky
- Family-friendly rentalsĀ United States
- Buffalo Trace Distillery
- Kentucky Exposition Center
- Kentucky Derby Museum
- Kentucky Kingdom & Hurricane Bay
- Louisville Slugger Field
- Churchill Downs
- Muhammad Ali Center
- Louisville Slugger Museum & Factory
- Angel's Envy Distillery
- Waterfront Park
- Falls of the Ohio State Park
- Big Four Bridge
- L&N Federal Credit Union Stadium
- Kentucky Science Center
- Kentucky International Convention Center
- James B Beam Distilling
- Jefferson Memorial Forest
- University of Louisville
- Castle & Key Distillery
- Bernheim Arboretum and Research Forest
- Marengo Cave National Landmark
- Frazier History Museum
- Evan Williams Bourbon Experience
- Four Roses Distillery Llc





