Vacation rentals in Highlands

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Quick stats about vacation rentals in Highlands

Total vacation rentals
Explore 130 vacation rentals in Highlands
Nightly prices starting at
Highlands vacation rentals start at G$8,351 GYD per night before taxes and fees
Verified guest reviews
Over 9,990 verified reviews to help you choose
Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 50 rentals that welcome pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wi-Fi availability
130 of Highlands vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highlands rentals
4.9 Average rating
Highlands stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Highlands

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

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Top guest favorite

Home in Highlands

4.9 out of 5 average rating, 616 reviews

Walk to everything • Quiet, Private, and Cozy

Tucked along a quiet, tree-lined street in Louisville’s Original Highlands neighborhood, you’ll find a cozy, private retreat filled with character and unique decor. Featuring a large master bedroom with king Sleep Number bed, a spacious living/dining room area, 2 full bathrooms, and a cozy full sized guest room. Walk to the best restaurants, boutiques, and coffee shops. Explore the nearby parks or unwind in your peaceful, historic hideaway. 1 mile from NULU 2 from downtown 5 from the Downs

ValueFamilySleep quality

Top guest favorite

The living room features a comfortable grey sectional couch and an accent chair positioned around a decorative fireplace with a stone surround. A flat-screen TV is mounted above the mantle, while natural light enters through large windows adorned with soft curtains.

Home in Highlands

4.98 out of 5 average rating, 109 reviews

Spacious Highlands Home-King Bed, Fire Pit & Yard

Tucked in the beautiful, historic Highlands, this spacious, pet-friendly 3-bedroom, 2-story home is minutes from the action! Grab a quick Uber to some of the most popular spots, such as the Bourbon Trail, coffee shops, or Nulu, then return to your relaxing, fully-fenced backyard oasis. Perfect for groups exploring the city by day and relaxing by the fire pit at night! Enjoy the best of both worlds with fast WiFi and a dedicated workspace if you need to log on remotely! Sleeps 8 and a king bed.

FamilyLocationIndoor spaces

Guest favorite

A two-story building is framed by lush greenery and a well-maintained exterior. The ground-level white porch is furnished with bright red chairs, flanked by steps leading to the entrance. A welcoming pathway runs between manicured bushes and trees, enhancing the inviting façade.

Home in Highlands

4.95 out of 5 average rating, 124 reviews

Highlands Lookout-3BR 3.5BA-Walk to Tons +Parking

Experience the best of Louisville from the heart of the Highlands on iconic Bardstown Road! 3/4 Bedrooms • 3.5 Baths Bonus Lounge with Queen Sleeper Sofa Private Balcony & Wet Bar Perfect for Bourbon Tours, Concerts, Bachelor/Bachelorette Trips & Group Getaways Off-Street Parking Walk to Louisville's best restaurants, bars, breweries, coffee shops, and nightlife. Minutes from downtown, distilleries, Churchill Downs, and the airport. Stylish, spacious and designed for memorable stays!

LocationFamilyQuiet

Top guest favorite

The living room features a spacious gray sectional sofa accompanied by a cozy throw. A decorative coffee table sits in the center, with a television mounted on the wall and a small side table with a lamp nearby. An ornate fireplace adds character to the space.

Home in Highlands

4.92 out of 5 average rating, 184 reviews

The Highland Fling - restaurant row, walk to all!

- ABSOLUTE BEST LOCATION!! LOUISVILLE'S RESTAURANT ROW!! - Sterilized Property - Superhost Property! - Charming house in Historic Highlands - 1 Block from Bardstown Rd - Restaurant Row - Walk to local shops and the BEST restaurants - Great backyard -1 full bath on first floor, one up -living room with sleeper sofa - Street parking for this residence - Fully stocked kitchen - 6.3 Miles to Churchill Downs - 2.8 Miles to Downtown/Convention Center - >1 Mile to Cherokee Park *NO locals*

ValueLocationSleep quality

Top guest favorite

A bright living area features a red sofa styled with decorative pillows, accompanied by two white accent stools. A uniquely designed coffee table with colorful artwork is positioned in the center. Hardwood floors and a patterned wall art enhance the welcoming space.

Home in Louisville

4.98 out of 5 average rating, 373 reviews

Velo Studio Flat / Paristown / Highlands /

Next to the The Highlands, this bike friendly house is in Paristown with great restaurants, Louisville Stoneware & an easy walk to Baxter & Bardstown Rd for nightlife. A clean, comfortable & stylish home in a quiet area. Five bicycles to access scenery nearby with a relaxing screened porch to unwind. Perfect for athletes, couples, families or business travelers. Cherokee Park is close with plenty of woods with trails for biking & hiking. Downtown, Big 4 Bridge & waterfront just 2 mi.

ValueLocationWalkability

Top guest favorite

The historic bungalow features a charming exterior with a light blue façade and a welcoming entryway. Lush greenery and flowering hydrangeas surround the stone steps, leading to the front door. The visible pathway is bordered by neat shrubbery, enhancing the inviting appearance of the property.

Home in Highlands

5.0 out of 5 average rating, 100 reviews

Bourbon Retreat • Walkable • Fire Pit • Parking

Stay in a beautifully restored historic Louisville bungalow designed for bourbon lovers, weekend getaways, and families exploring NuLu. End your evenings around the fire pit, wake up with artisan coffee, and spend the day walking to Louisville's best restaurants, bars, and distilleries. ✔ Bourbon Lounge in the house ✔ 9 distilleries within 2 miles ✔ Comfortable bedrooms/quality linens ✔ Walk to restaurants/bars-5 min to Nulu ✔ Outdoor fire pit ✔ EV Charger ✔ Curated Coffee Bar

FamilyLocationAccess

Superhost

A well-lit living area features a gray sectional sofa and a mounted television. Natural light enters through large windows lined with sheer curtains. A dining table is positioned in the background, complemented by chairs and a glimpse of the kitchen area.

Apartment in Highlands

4.79 out of 5 average rating, 127 reviews

The Bardstown-Louisville Nightlife

This spacious unit provides a front row seat to watch and experience Louisville from the comfort of your own private retreat in the middle of the best street in Louisville. Feet from many restaurant , bars and boutiques. During your stay spend time walking the neighborhood filled with boutiques, restaurants, bars, distilleries and art galleries. Start the bourbon trail or walk to the famous Cave Hills Cemetery. Private gatherings are allowed but house rules must be followed.

ValueFamilyCheckout

Guest favorite

A welcoming living area features a large flat-screen TV mounted above an ornate fireplace. Two comfortable leather sofas are arranged around a glass coffee table on a patterned area rug. The space is illuminated by a modern chandelier, with natural light filtering through sheer curtains.

Home in Highlands

4.95 out of 5 average rating, 315 reviews

Eclectic Historic House in the Highlands

Situated in the Highlands neighborhood, our large 1900 Victorian duplex is the perfect retreat for you and your group during your next visit to the Derby City! Our home sits on a quiet street, just a few minutes’ walk away from Baxter Ave/Bardstown Rd, which offers ample bars, restaurants, and night clubs. Our home is also just a short drive to downtown/waterfront, UoL's campus/Churchill downs, the airport, and other great Louisville neighborhoods. We can’t wait to have you!

ValueFamilyNearby

Superhost

A bright living area showcases comfortable seating, including a cheerful yellow armchair. A large smart TV is mounted on the wall, complemented by a simple indoor plant. An airy window allows natural light to fill the space, creating a welcoming atmosphere.

Apartment in Highlands

4.85 out of 5 average rating, 220 reviews

Highlands Airy Retreat- No Hassle Checkout

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.

LocationFamilyAir conditioning

Top guest favorite

A charming balcony features a wooden table surrounded by four slatted chairs. A potted fern hangs gracefully from the angled ceiling, with views of lush greenery visible beyond the railing, creating a serene outdoor space.

Guesthouse in Louisville

4.98 out of 5 average rating, 336 reviews

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.

LocationFamilyLong stay

Guest favorite

Home in East Market District

4.88 out of 5 average rating, 149 reviews

Butchertown 1BR | Walk to NuLu | Free Parking

Stay in Louisville's Historic Butchertown, just steps from the restaurants, breweries, boutiques, and bourbon experiences of NuLu. This beautifully renovated first-floor 1-bedroom apartment combines historic character with modern comfort, featuring soaring 11-foot ceilings, exposed brick chimneys, a spacious open-concept living area, a fully equipped kitchen, dedicated workspace, Smart TVs, and free parking for a convenient city stay.

LocationValueBathroom

Superhost

A cozy bedroom features a sturdy wooden bed framed by checkerboard bedding in blue and white, complemented by a floral wall art piece above. Two bedside lamps provide soft lighting, and neatly rolled towels are displayed on the bed.

Apartment in Highlands

4.84 out of 5 average rating, 195 reviews

Budget Friendly Walkable area 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

ValueFamilyAccuracy