Family-friendly holiday rentals in Original Highlands, Louisville

4.86 out of 5 average rating, 315 reviews

Cottage in Germantown

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.

4.94 out of 5 average rating, 393 reviews

DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT

- 3 min drive to U of Louisville - 5 min drive to KY Expo Center - 7 min drive to Louisville Zoo This gorgeous 3-bed, 2-bath house is less than 4 miles from downtown Louisville. With its fully-equipped kitchen, spacious rooms & completely renovated kitchen, the house is the perfect base for large groups wanting to explore the city. Enjoy the wide variety of shops, restaurants, & bars nearby. Kentucky Derby fans love the close proximity to Churchill Downs. No Children for Derby No Locals Please

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!

4.96 out of 5 average rating, 264 reviews

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

4.93 out of 5 average rating, 196 reviews

Apartment in Highlands

Large Townhouse, Walk to All! King beds, 2.5 baths

Large, 3 story townhouse sleeps 6 in 1600 sq. ft. Step out the door to best walking neighborhood in Louisville. Great coffee shop 150 ft. away, with a dozen places to eat, from fancy to casual, within the block. Parks, movies, live music are 10 minute walk or less away. 2 King bedrooms, each with full bath, 1 queen and 1 twin daybed w/ trundle. Fully equipped kitchen, 3 large smart tvs, wifi and cable! Kitchen fully equipped, from quality appliances to pots/pans/plates/cutlery/glasses/etc.

Superhost

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.

Home in Central Business District

4.83 out of 5 average rating, 212 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.

4.86 out of 5 average rating, 165 reviews

Cottage in Prospect

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.

4.96 out of 5 average rating, 310 reviews

Bungalow in Germantown

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!

4.93 out of 5 average rating, 262 reviews

Flat in Louisville

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.

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.