Vacation rentals in Original Highlands, Louisville

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Top-rated vacation rentals in Original Highlands, Louisville

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Home in Highlands

*Gorgeous common space w/ sunlight & powder area!*

The Highlands Hideout is an 1800 square foot, lofted, tranquil space with endless natural light and a wide open first floor area; perfect for enjoying time with friends, family, and/or loved ones! Once you step outside you are immediately immersed in Louisville’s most popular/historic neighborhood, the Highlands, as you’re a mere 150 feet from Bardstown Road. Make the Hideout your space to relax and recover after taking in all the food, shops, and bars that make Louisville unique.

$110 per night

Superhost

Apartment 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.

$101 per night

Superhost

Apartment in East Market District

Walk Everywhere! NuLu/Butchertown Derby Loft

- Heart of East Market Arts District - Distilleries, breweries, coffee shops, boutiques, parks, festivals, and a plethora of local bars and restaurants ~ 1 block! - Keyless entry, 2nd floor unit - 130 year old renovated property on a quiet, tree-lined street - Ample free street parking!

$91 per night

Other great vacation rentals in Original Highlands, Louisville

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Superhost

Apartment in Louisville

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.

$109 per night

Superhost

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.

$100 per night

Superhost

Condo in Highlands

Custom 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.

$96 per night

Superhost

Loft in Butchertown

Chic Cozy Queen Apt., Coffee, Min. to Downtown!

Reserve this beautiful loft located in the historic Butchertown neighborhood just minutes from downtown, and all of the fun that Louisville has to offer! Enjoy a comfortable stay surrounded by 1800s brick walls, rustic décor, and peace and quiet! Wake up from a peaceful night’s sleep on a memory foam mattress to enjoy a cup of coffee before checking out the local distilleries, museums, or Churchill Downs! In town on business? Try out our desk nook and fast Wi-Fi! Book today!

$47 per night

Superhost

Home in Louisville

Urban spot close to breweries, distilleries & more

Welcome to "The Hamilton House" Air B&B nestled between the Highlands and Nulu in the Paristown neighborhood. This amazing Louisville getaway boasts an unbeatable outdoor experience. In addition, you will be be within walking distance of excellent dining, breweries, and entertainment and within easy driving distance to all that downtown Louisville offers as well.

$110 per night

Superhost

Apartment in Highlands

Highly Rated Highlands Retreat- Central Location

NEW LISTING! Welcome to "Birdie". The cutest, most conveniently located home in the city. From head to toe, Birdie is decked out with all the ingredients for a fun, relaxing Louisville stay. Occupying the 2nd floor of a beautiful Victorian home, Birdie 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.

$72 per night

Superhost

Condo in Louisville

Huge Highlands Townhouse, Walk to All!

Large, 3 story townhouse sleeps 8 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.

$129 per night

Superhost

Apartment in Butchertown

The Point at Story and Frankfort Avenue

Brand Spankin New to Airbnb!! Unit is a spacious and completely renovated one bedroom (king) apartment. Very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.

$69 per night

Superhost

Apartment in Germantown

Urban Bourbon Hub- Lg 1bd/2ba in the Highlands!

Spacious 1st floor apartment in a Victorian duplex home in the heart of the Highlands/Germantown. 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!

$96 per night

Superhost

Condo in Louisville

❤️Spacious Flat Near Bardstown Rd w/Free Parking

This space is specifically catered to provide you with the ultimate experience in Louisville! Located near Cherokee Park and Gravely Brewery. Or walk to any of the marvelous *Brunch Spots *Coffee Shops *Breweries *Boutiques If there are any accommodations that you need feel free to reach out and let us know! Near NuLu neighborhood 🌟

$118 per night

Superhost

Apartment in Louisville

Taste of KY Studio @ Bungalou + Bourbon Bar + Game

Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oasis discreetly hidden behind Award-Winning "NEAT Bourbon Bar + Bottle Shop" on iconic Bardstown Rd. Regardless of your group size (1, 2, 10 or 50 guests)...we got ya covered! Cherry-pick between 10 Distinct Suites, or splurge on one of our 7 “Group Packages" - outstanding for any and all special occasions. **Details for this Specific Booking Below** 21+ Older Policy For ALL Guests

$127 per night

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