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, 396 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

Superhost

Home in Crescent Hill

4.79 out of 5 average rating, 156 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.

4.92 out of 5 average rating, 124 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.

4.97 out of 5 average rating, 246 reviews

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

*Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required* Germantown is a unique blend of past and present. Restaurants and local attractions including Monnik Beer Company and historic Nords Bakery just blocks away from the home, there is something for everyone. Conveniently located within reach of several desirable destinations - The University of Louisville, Churchill Downs, downtown Louisville and the NuLu district nearby.

Home in Central Business District

4.83 out of 5 average rating, 213 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.

Guest suite in Louisville

4.96 out of 5 average rating, 371 reviews

Cherokee Park Oasis with Private Entrance

1 bdrm basement apartment with private entrance, bedroom, bathroom, and common area located adjacent to Cherokee Park. Owner occupies the main floor upstairs. 3/4 mile walk to shops, restaurants, and entertainment on Bardstown Rd. Heated saltwater swimming pool and cabana with wet bar. Centrally located within 10 minutes from downtown, Churchill Downs, the Zoo, the airport, golf courses and Kentucky Kingdom. Situated in a quiet, park-like neighborhood with ample parking.

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, 263 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, 223 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.