Holiday rentals in Original Highlands, Louisville

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Top-rated holiday rentals in Original Highlands, Louisville

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Guest favourite

Flat in Louisville

4.94 out of 5 average rating, 284 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.

Top guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 137 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Guest favourite

Loft in Butchertown

4.93 out of 5 average rating, 204 reviews

Chic & Cozy Queen Apt – Coffee & Mins to Downtown!

Reserve this stylish 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 12” memory foam mattress to enjoy a complimentary 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!

Guest favourite

Home in Germantown

4.93 out of 5 average rating, 170 reviews

Private Parking in GTownWalk to Coffee,Shops,Bars!

Shotgun Rye is ready to host your stay in Louisville! Located close to everything cool in Germantown and Highlands area! People visit for Bourbon Tours, Ky Derby, Conventions, Expo Ctr, UL graduations and sporting events, live music and so much more! Completely remodeled with all the modern conveniences & a comfortable, casual touch. But with so much to see and do in Louisville you’ll load up your itinerary with unforgettable experiences. Great location walk to bars, restaurants and shopping!

Guest favourite

Home in Highlands

4.91 out of 5 average rating, 180 reviews

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

Guest favourite

Flat in Highlands

4.91 out of 5 average rating, 154 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.

Top guest favourite

Flat in Louisville

4.95 out of 5 average rating, 128 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⚜️

Top guest favourite

Apartment in Butchertown

4.98 out of 5 average rating, 100 reviews

The Hilltop Hideaway

Come hunker down at The Hilltop Hideaway, a centrally-located historic 19th-century shotgun style cottage perched atop Clifton’s hills. Perfect for a couple’s getaway, a friends’ rendezvous, or a creative’s retreat, you may find yourself not wanting to leave. But the location couldn’t be better, with Frankfort Ave’s restaurants, coffee shops, and bars all within walking distance, and nearby entertainment options plentiful with Butchertown and NULU only minutes away.

Guest favourite

Flat in Louisville

4.96 out of 5 average rating, 138 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. .

Top guest favourite

Flat in East Market District

4.97 out of 5 average rating, 156 reviews

Dreamy, Designer-Curated Shoppable Retreat

A thoughtfully curated rental by Jaclyn Journey Hospitality, designed with intention to make you feel taken care of when staying away from home. Featured in Architectural Digest, DOMINO magazine, Apartment Therapy & others. With every item hand-selected to enchant the senses, this rental is shoppable, encouraging you to take your favorite piece of your trip back with you.

Guest favourite

Flat in Highlands

4.88 out of 5 average rating, 159 reviews

Walk to Bars & Restaurants | 1BR Highlands Stay

Prime Location in Louisville’s Most Walkable Area! Just 7 minutes to the KFC Yum! Center with dedicated parking and steps from hundreds of shops, bars, and restaurants. This comfortable, well-equipped home offers exceptional value for your stay. Enjoy: •Easy self check-in with keypad •Photo-guided check-in instructions •Stocked kitchen for cooking •Roku TV & free Wi-Fi

Top guest favourite

Home in Louisville

4.97 out of 5 average rating, 379 reviews

The Highlands Condo/Roof Deck

Our brand new renovated 1 BR 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 area, 12 minutes from the airport. Walking distance to many great restaurants, bars, shops , and parks.