Apartment holiday rentals in Original Highlands, Louisville

4.95 out of 5 average rating, 291 reviews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

4.83 out of 5 average rating, 130 reviews

Highlands Harmony House - Near Cherokee Park

Upstairs; full sized Studio Apartment with large bedroom, kitchen, separated bath, private, big screened porch! The PRIVATE bathrooms are in the hall -3 feet from your bedroom/hidden behind privacy screens. "Yes, you can run to the bathroom in your 'all-together!" You'll love the kitchen and comfortable queen bed. Very cozy! Private screened porch overlooks our artistic/wooded backyard! Located on a quiet dead end street. Stroll our shady sidewalks to local bars coffee shops, restaurants etc.

Flat in Original Highlands

4.93 out of 5 average rating, 126 reviews

Vintage yet Modern Highlands home! Walk to venues!

Spacious 1st floor apartment in a Victorian duplex home in the heart of the Highlands/Germantown. We are ready to host for short, mid & long term! Because of our close proximity to Louisville’s vibrant nightlife, eclectic dining scene & shopping it’s no wonder visitors flock here to get a taste of something amazing! Perfect place for your Ky Derby home base! Walk down to the hottest Arts & Music venue in town- Old Forester Paristown Hall! Don’t forget about the Bourbon tours and new breweries!

Flat in East Market District

4.97 out of 5 average rating, 268 reviews

Urban Bourbon Stay - Nulu 2 BR * 2 Full Bath

Beautifully renovated historic 2 bedroom 2 full bath apartment in Louisville's hip Nulu neighborhood. Huge 1,500 sq ft space to relax in after enjoying all the shops and restaurants in the Nulu area. This apartment is just a few blocks east of downtown. It's a great area to kickoff your Louisville adventures. This apartment is above a boutique wine and bourbon shop and within walking distance of several distilleries, so you don't have far to go to sample some of Kentucky's legendary bourbon.

4.94 out of 5 average rating, 120 reviews

Hangover House, a cool spot above a cool bar

HangOver at our House! This spacious apartment located directly above theMerryWeather bar in Schnitzelburg can sleep up to 4. Large bedroom features a queen bed, DVD/TV, tons of natural light, and French doors for privacy. Living room has sofa bed and flat screen smart TV. Eat-in kitchen also has laundry. Throw some darts in the front lounge! And you're just a short walk to a variety of bars, restaurants, retail, and grocery. FOR NIGHT OWLS ONLY! YOU'LL BE SLEEPING ABOVE A BUSY, NOISY BAR.

Flat in Original Highlands

4.86 out of 5 average rating, 613 reviews

Walkable, 1920s bungalow in Historic Highlands

Beautifully renovated, 800 sq ft, 2 Bedroom, 1 bath apartment centrally located in the historic Highlands neighborhood. Small but efficient kitchen for staying in, and a coffee bar in the dining room, to get you moving. Excellent restaurants, coffee shops, and boutique shopping within a few blocks. Beautiful Cave Hill Cemetery, and Cherokee Park are nearby, as well as a playground and dog park just a block away. A Walgreens is just a few steps away for groceries, etc.

Flat in Original Highlands

4.91 out of 5 average rating, 157 reviews

Highlands Midcentury Getaway w/ Firepit & King Bed

NEW LISTING! Welcome to "Ruby"- the coolest, most conveniently located home in the city. From head to toe, Ruby is decked out with all the ingredients for a fun, relaxing Louisville stay. Occupying the first floor of a beautiful Victorian home, Ruby is walking distance to restaurants and the urban bourbon trail, as well as hospitals and downtown businesses. The location truly can't be beat! Drive or Uber to the Yum center, NULU, Lynn Family Stadium, and the waterfront in no time.

4.95 out of 5 average rating, 133 reviews

Highlands Zen Oasis • Comfy, Clean & Cozy

Awesome Sweet Spot of a Louisville Location! This PRIVATE APT. with SELF CHECK IN + FREE PARKING is in a beautiful, safe neighborhood in the historic Highlands. Quick 2-min walk to magnificent Cherokee Park OR charming Bardstown Road - a multitude of eclectic galleries, bars, restaurants & shops to explore! Conveniently (5-10 min) located to Churchill Downs, Downtown Louisville, Louisville Seminary, NuLu, UofL, Bellarmine, Fair & Expo Center, Yum Center, Waterfront & the Airport⚜️

4.98 out of 5 average rating, 126 reviews

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

4.95 out of 5 average rating, 399 reviews

Sunny Clifton Loft

Recently renovated studio apartment with loads of natural light, steps from award-winning local restaurants, bakeries, bars, and housed above our independent record store. We do our best to AirBnB ethically & responsibly.. Revenue from this unit helps to 1) keep on-site residential rents affordable & increase-free 2) maintain the historic building & protect it from outside development while 3) help us steer our future as a brick and mortar independent business.

4.96 out of 5 average rating, 141 reviews

Sun-filled Phoenix Hill Studio

Located in the Phoenix Hill neighborhood, it's a short 11 minute walk to East Market District restaurants and attractions or a 15 minute walk to Gravely and other Original Highlands destinations. 11 minute drive to Churchill Downs 5 minute drive to the Highlands 4 minute drive to East Market restaurants and shopping. Ample Lyft and Uber drivers in this neighborhood to take you anywhere you want to go. .