Vacation rentals in Original Highlands, Louisville

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Top-rated vacation rentals in Original Highlands, Louisville

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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, 100 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

The exterior of the river house features a large covered deck with a wraparound porch. Outdoor seating areas are visible, framed by greenery and shaded by a sloped roof. Glass doors open to the interior, allowing an inviting flow between inside and outside spaces.

Home in Elizabeth

4.86 out of 5 average rating, 183 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 favorite

A comfortable living area is featured with a plush sectional sofa, a modern coffee table, and a large flat-screen TV mounted on a white media console. Wooden flooring extends throughout the space, complemented by a stylish area rug. Warm lighting is provided by recessed fixtures above.

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.

Guest favorite

A fully equipped kitchen features modern appliances, including a stainless steel refrigerator and a stove. A spacious island with bright yellow stools sits beneath pendant lighting. Exposed beams and a wooden floor complement the brick walls, while windows allow natural light to enhance the atmosphere.

Loft in Central Business District

4.93 out of 5 average rating, 92 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

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.

Guest favorite

An outdoor rooftop terrace features sleek gray tiles and a selection of wooden furniture, including high tables and benches. The city skyline is visible in the background, showcasing a mix of modern and historic buildings beneath a clear blue sky.

Apartment in Central Business District

4.9 out of 5 average rating, 100 reviews

4th Street Suites - Comfortable King Bed Suite

Embark! Your refuge boasts a regal King Bed, a kitchen of sheer beauty, and streaming delights. Yet, it's the spellbinding allure of the resort pool, hot tub tales, golf dreams, and the lofty 7th-floor haven that set this place ablaze. With free parking and the pulsating energy of 4th Street Live at your doorstep, don't miss out! Secure your slice of luxury—book now for an unforgettable escape! Pool/hot tub schedule subject to change at the discretion of the property management company.

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!

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

The home's welcoming facade features a covered front porch with seating arrangements. A set of stairs leads to the entrance, framed by decorative railings. Fresh landscaping, including small shrubs and mulch, enhances the outdoor space, while trees provide partial shade.

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).

Top guest favorite

The exterior of a two-story building is illuminated by soft string lights, creating a welcoming ambiance. A well-maintained garden with greenery is visible, along with a patio area featuring several chairs arranged around a fire pit. The entrances are framed by dark, contrasting doorways.

Apartment in Louisville

4.93 out of 5 average rating, 84 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.