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.

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Guest favorite

A welcoming entrance is highlighted by a set of stone steps leading to a covered porch. Vibrant flowers enhance the greenery, while elegant architectural details are seen on the house. The porch features a decorative railing and a couple of seating areas for relaxation.

Apartment in Louisville

4.83 out of 5 average rating, 127 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 favorite

A rooftop view reveals a mix of modern skyscrapers and historic buildings in downtown. The skyline is framed by a plush seating area adorned with colorful cushions, inviting relaxation while enjoying the urban landscape. The scene is calm, with soft light illuminating the structures.

Apartment in Central Business District

4.99 out of 5 average rating, 99 reviews

Sleek Luxury Apt: King Bed, Coffee Bar & Pool!

Stay in splendor as you enjoy the endless amenities and stylish touches this apartment has to offer! Enjoy a peaceful night's sleep on a comfortable mattress, and start your day with a complementary cup of coffee. Get a workout in the gym, hang out at the rooftop or walk around downtown. Being in the heart of downtown, the opportunities and activities are endless! To end the night, relax with a glass of wine and watch a movie on Hulu or Disney plus! Don't wait! Book your stay with us today!

Guest favorite

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 favorite

A spacious walk-in shower is featured, showcasing dual shower heads mounted on opposing walls. The glass enclosure provides a bright and airy feel, while sleek white tiles enhance the contemporary design. Shelves are positioned inside for convenience.

Condo 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 6 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.

Superhost

A modern kitchen features sleek stainless steel appliances and a marble-topped island with seating for three. A textured brick wall adds character, while ample natural light fills the space through large windows, enhancing the contemporary design of this fully renovated area.

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 favorite

A spacious bedroom features mirrored closet doors and large windows overlooking the water. The room is equipped with a brightly colored quilt, neatly arranged towels, and a cozy armchair, inviting relaxation while taking in the serene views.

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!

Top guest favorite

A serene view of the river is presented, with gentle ripples reflecting the sky. Colorful flowering trees frame the scene, with three boat docks visible along the water's edge. A bridge can be seen in the background, connecting both sides of the river.

Home in Jeffersonville

5 out of 5 average rating, 19 reviews

Beautiful RiverHouse

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 .

Superhost

The kitchen features wooden cabinetry and a double sink, with a plate of cookies resting on the counter. Breakfast items are displayed, while a dining area with a round table and four chairs is visible in the background.

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 favorite

An open loft bedroom features a spacious bed dressed in soft linens with decorative pillows. A large window allows natural light to flood the room, while a ceiling fan helps with airflow. A comfortable seating area is visible in the background.

Home in Louisville

4.91 out of 5 average rating, 157 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 favorite

A bright living area features a striped green sofa and a matching chair, complemented by a glass coffee table. A large wall art panel displays abstract shapes against a white backdrop. A soft area rug covers the wooden floor, enhancing the space's comfort.

Apartment in Louisville

4.93 out of 5 average rating, 83 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.

Guest favorite

An outdoor area features a cozy gazebo with soft lighting, surrounded by lounge furniture. A hot tub with illuminated water sits nearby, while decorative stones and plants add to the tranquil environment. Fenced in for privacy, this space is ideal for relaxation.

Home in New Albany

4.95 out of 5 average rating, 146 reviews

king bed and oasis backyard with hot tub

11 miles to Derby. Come enjoy our newly decorated house with a hot tub, gazebo outdoor fun area and lounge furniture and wood burning fire pit. The idea is to both indoor and outdoor give you a great experience that not everyone offers! We sleep 4 adults comfortably in our 1 KING size bedroom and 1 QUEEN size bedroom. We're located in a quiet neighborhood with a fully fenced in backyard and we're Pet Friendly with a fee!

Superhost

A three-story blue townhome is framed by lush green trees and a well-maintained front yard. Two ornate white planters with red floral arrangements are positioned near the entrance, which features a red door and a charming black wrought-iron porch railing.

Home in New Albany

4.87 out of 5 average rating, 60 reviews

Modern Townhome on Mansion Row w/Pool Table

Have fun with the whole family at this stylish townhome on Mansion Row. Enjoy the 8’ pool table, watch the big game in HD on the huge projector screen or have a game night on the touch screen gaming table (includes Monopoly, Life, Sorry, etc.). Centrally located between downtown Louisville & Caesar’s Casino in Southern Indiana, this is the perfect place to call home while enjoying all that Louisville has to offer.