Holiday rentals in Original Highlands, Louisville

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Top-rated holiday rentals in Original Highlands, Louisville

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

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Guest favourite

Villa in Old Louisville

4.88 out of 5 average rating, 17 reviews

~Gorgeous & Spacious Villa ~ Prime Old Louisville~

From BNB Louisville - Discover a haven of tranquility in our completely renovated cottage, where every detail whispers luxury and comfort. Wrapped in the warm embrace of exposed brick walls, the cottage's soulful character merges with an award-winning high-end design. The living space is thoughtfully furnished to provide a cozy yet elegant ambiance. And a spa-like bathroom designed to offer a rejuvenating experience with its sophistication and serene decor. Perfect for small families, couples or

Guest favourite

Flat in Louisville

4.83 out of 5 average rating, 126 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.

Guest favourite

Home in Elizabeth

4.86 out of 5 average rating, 182 reviews

Relaxing River House Retreat-Sleeps 10-12

Cozy newly renovated river house with ample entertainment space inside and out. Large covered deck with wrap around porch and a beautiful view of the Ohio River. 1 mile from Horseshoe Casino, just minutes from entertainment and amenities of downtown New Albany, IN and Louisville, KY. Less than 10 minutes from a local winery, 2 breweries, and Chariot Run Golf Course. Perfect for large groups or a romantic weekend getaway! Additional detached bonus bedroom. $100 extra per stay at guest's request.

Guest favourite

Home in Louisville

4.93 out of 5 average rating, 45 reviews

SuperHost ~ Historic Haven near heart of Downtown!

Welcome to this stunning historic gem nestled in the heart of Louisville! This beautifully preserved home boasts timeless architectural details, including original hardwood floors, ornate moldings, and classic bay windows - offering a perfect blend of vintage charm and modern comforts. Located just minutes from downtown Louisville, you'll enjoy easy access to restaurants, cultural attractions, and parks. Experience the best of both worlds—historic charm and urban living in this enchanting home!

Guest favourite

Apartment in Highlands

4.93 out of 5 average rating, 196 reviews

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

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.

Top guest favourite

Home in Jeffersonville

5 out of 5 average rating, 19 reviews

Beautiful RiverHouse

Pickleball and beautiful water views with this spacious home on the river close to downtown Louisville and Jeffersonville! Have your secret getaway place that is so calming and close to all the activities of the big city close by! Everyone can enjoy this 4 bedroom 3 1/2 bath home that can sleep 14+ people comfortably . All 3 stories of this home have breathtaking views of the river. There are lots of games for family and a Pickleball court available by reservation. Elevator also available .

Guest favourite

Loft in Central Business District

4.93 out of 5 average rating, 91 reviews

Historic Nulu Loft| Downtown | Bourbon Trail

Our industrial loft is located in the historic Central Business District and NuLu area of Louisville. Local history mixes with a trendy and vibrant neighborhood known for its eclectic mix of art galleries, restaurants, and shops. The loft is situated close to all amenities and major attractions in downtown Louisville, including the popular Whiskey Row, Museum Row, Bourbon Trail and Louisville Slugger Field. We are a quick 12min drive to historic Churchill Downs, home of the Kentucky Derby.

Superhost

Home in Old Louisville

4.84 out of 5 average rating, 89 reviews

Exposition Center, Bourbon Trail, Downtown, & I65

Our guest will enjoy easy access to everything from this centrally located home. Right off of interstate 65. Conveniently located near downtown (2 miles), University of Louisville (1.1 miles), Cardinal Stadium (1.9 miles), Yum Center (2.3 miles), Churchill Downs (2.8 miles), Kentucky Exposition Center (3.1 miles), Louisville International Airport (3.9 miles), and many more local attractions. This home has been fully renovated and has two off street parking spaces in the rear of the house.

Top guest favourite

Home in Louisville

4.95 out of 5 average rating, 171 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Superhost

Home in Louisville

4.72 out of 5 average rating, 29 reviews

The Shaded Retreat

Kick back & relax in this calm, stylish space. Designed for long-term stays. Traveling medical workers & project work teams will find this a perfect fit. Flexible sleeping arrangements: accommodates 5 extra large twin beds and 1 queen bed. Deep discounts for longer stays. The second bathroom is set for renovation but is fully functional. It's connected to the laundry room and back door. For guest with pets it a great space to clean paws before entering the main house.

Guest favourite

Home in Louisville

4.91 out of 5 average rating, 156 reviews

New Signature Highlands Home- steps away from…

Welcome to our new to AirBNB Highlands home. Recently redecorated and updated, this home is steps away from many incredible local restaurants, bars, and shops. Less then one mile to Cherokee Park. Less then five miles to Churchill Downs, NULU, and the airport. You simply can’t beat this location. Safe, family friendly neighborhood with swing-set in the back yard (high chair, pack and play, toys, and more available upon request).

Guest favourite

Flat in Louisville

4.93 out of 5 average rating, 82 reviews

Home Away from Home, Unit 3

Located directly on Bardstown Rd in Louisville's historic Highlands neighborhood. Newly renovated with outdoor space, walk/bike to 30+ restaurants, 6+ coffee shops, bookstores, grocery stores, a movie theater, 20+ local shops and boutiques, wine shops & much more. Walkability Score 88, Bike score 79 Flat as a pancake, good bike lanes. Bedding, towels & amenities. Keyless entry, free private parking, & washer/dryer in building.