Family-friendly vacation rentals in Original Highlands, Louisville

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Top-rated family-friendly rentals in Original Highlands, Louisville

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Louisville
ArTisTs CoTTaGe
Enjoy peaceful privacy and 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. Granite countertops. Picture 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.
Nov 16 – 23
$116 per night
4.96 out of 5 average rating, 165 reviews
Guest favorite
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.
Jun 13 – 20
$93 per night
4.99 out of 5 average rating, 233 reviews
Guest favorite
Apartment in Highlands
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!
Oct 14 – 21
$93 per night
4.92 out of 5 average rating, 157 reviews

Popular amenities for Original Highlands, Louisville family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Louisville
Southern Comfort-Hottub wlk 2 Resturant Row & Shop
Aug 21 – 28
$411 per night
4.92 out of 5 average rating, 140 reviews
Guest favorite
Home in Louisville
2 Living Rooms Close 2 Shopping & Restaurants
Jan 2 – 9
$254 per night
4.99 out of 5 average rating, 213 reviews
Guest favorite
Guest suite in Jeffersonville
Relax w/hot tub & movies on 110 in screen
Feb 8 – 15
$199 per night
4.93 out of 5 average rating, 166 reviews
Superhost
Home in Louisville
Sleeps 16, Highlands Area, Heated Pool, Hot tub
Dec 25 – Jan 1
$884 per night
4.95 out of 5 average rating, 128 reviews
Guest favorite
Home in Jeffersontown
Country Setting/ Tropical Feel
Oct 13 – 20
$275 per night
4.95 out of 5 average rating, 65 reviews
Guest favorite
Home in Louisville
Great patio - Northeast Louisville
Dec 24 – 31
$733 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Louisville
2.0 Southern Comfort Highlands-Cherokee Triangle
Jul 19 – 26
$523 per night
5.0 out of 5 average rating, 26 reviews

Family- and pet-friendly home rentals

Guest favorite
Apartment in Louisville
Unique Studio in the Highlands
Mar 10 – 17
$80 per night
4.91 out of 5 average rating, 439 reviews
Guest favorite
Home in Highlands
Charming Home in the Highlands
Aug 24 – 31
$144 per night
4.9 out of 5 average rating, 461 reviews
Guest favorite
Condo in Louisville
Huge Highlands Townhouse, Walk to All!
Jun 20 – 27
$201 per night
4.95 out of 5 average rating, 151 reviews
Superhost
Home in Louisville
NuLu Private Home|Backyard|Parking
Apr 11 – 18
$166 per night
4.86 out of 5 average rating, 124 reviews
Guest favorite
Guest suite in Louisville
One Room Apartment with Private Off Street Parking
Sep 30 – Oct 7
$49 per night
4.94 out of 5 average rating, 120 reviews
Guest favorite
Home in Louisville
DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT
Dec 30 – Jan 6
$163 per night
4.93 out of 5 average rating, 317 reviews
Superhost
Home in Central Business District
615 E Washington, Nulu Bourbon Trail
Jul 28 – Aug 4
$305 per night
4.82 out of 5 average rating, 184 reviews
Superhost
Home in East Market District
Home Away from Home - DT/Phoenix Hill/ Nulu areas
Oct 28 – Nov 4
$199 per night
4.9 out of 5 average rating, 379 reviews
Superhost
Guesthouse in Crescent Hill
Park Carriage House. Rest & Explore with Hollyhock
Feb 25 – Mar 4
$175 per night
4.88 out of 5 average rating, 106 reviews
Guest favorite
Guest suite in Louisville
Spacious Lower-Level in Quiet Neighborhood
Jul 28 – Aug 4
$117 per night
4.98 out of 5 average rating, 172 reviews
Guest favorite
Guesthouse in Louisville
Charming Carriage House with 2 private baths.
Jul 19 – 26
$93 per night
4.93 out of 5 average rating, 281 reviews
Guest favorite
Home in Louisville
The Camp Taylor Cottage Close to Airport/ Downtown
Jul 28 – Aug 4
$126 per night
4.88 out of 5 average rating, 239 reviews

Family-friendly home rentals with a pool

Guest favorite
Guest suite in Louisville
Cherokee Park Oasis with Private Entrance
Apr 8 – 15
$112 per night
4.96 out of 5 average rating, 354 reviews
Guest favorite
Home in Louisville
Entire House in The Highlands. Private Pool.
Oct 21 – 28
$361 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Home in Louisville
Spacious Ranch- Large Groups/Families
Oct 25 – Nov 1
$765 per night
4.96 out of 5 average rating, 25 reviews
Guest favorite
Guesthouse in Shepherdsville
Bourbon Country/ Derby Guest House
Apr 18 – 25
$195 per night
4.96 out of 5 average rating, 47 reviews

Quick stats about vacation rentals that are family-friendly in Original Highlands, Louisville

Total rentals

80 properties

Wifi availability

80 properties include access to wifi

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Total number of reviews

5.3K reviews

Nightly prices starting at

$50 before taxes and fees

Destinations to explore