House vacation rentals in Original Highlands, Louisville

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Popular amenities for Original Highlands, Louisville house rentals

House rentals with a pool

A serene backyard features a sparkling pool surrounded by landscaped gardens, including various shrubs and decorative stones. The house, characterized by a brick facade and a sloped roof, provides a welcoming backdrop under a clear blue sky.
Home in Louisville
4.61 out of 5 average rating, 46 reviews

Louisville KY Home w/Hot Tub & Pool

AlprenticeRating, 5 stars4 months ago
Great place to stay!! Kids will love it & adults will, as well! Very spacious in a peaceful neighborhood. Would definetly stay here again!
Guest favorite
A split-level home is displayed, featuring a combination of brick and siding. A well-maintained garden with vibrant flowers lines the front. A mature tree provides shade, and the house is accented with dark shutters beside the windows. A welcoming sign is visible in the yard.
Home in Louisville
4.9 out of 5 average rating, 10 reviews

The Getaway!

TrinaRating, 5 stars2 days ago
The house was absolutely perfect. So was the location. I would stay here again and again. The host is proactive, sending lots of information before I had even arrived. It’s been my favorite stay by far.
Top guest favorite
A spacious outdoor pool is surrounded by lounge chairs under tall trees. A multi-level pavilion stands in the background, offering shaded areas. The clear blue water reflects the sunny sky, creating an inviting space for relaxation and leisure.
Home in Prospect
5 out of 5 average rating, 9 reviews

NEW Bourbon Trail, Pet Friendly, Downtown, Shops

EthanRating, 5 stars1 week ago
My family had a great stay at this beautifully furnished home. It is centrally located within the pristine Norton Commons community, and it is close to many shops and restaurants. Great place to make home base for a trip to Louisville!
Superhost
A vibrant basement game area is illuminated by soft blue lighting. A pool table is positioned at the center, surrounded by stylish seating at a bar counter in the background. The walls are adorned with cues and there is a cozy ambiance throughout the space.
Home in Louisville
4.85 out of 5 average rating, 26 reviews

Near Bourbon Trail, expo, 3 beds, off Outerloop

ElizabethRating, 5 stars1 week ago
Great for our little vacation with the kids. Great to have the pool and the game room in the basement.
Top guest favorite
A spacious backyard is illuminated by string lights at dusk, featuring a hot tub and multiple seating areas around a fire pit. The well-maintained lawn and patio area create a welcoming outdoor space for relaxation and gatherings.
Home in Louisville
4.97 out of 5 average rating, 248 reviews

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

BrianRating, 5 stars1 month ago
This house is absolutely fantastic. Super clean, super comfortable. The beds and pillows are amazing. I would highly recommend this house for any gathering. We were a group of four men doing bourbon trail related things, and relaxing at night next to the fire pit and in the hot tub.
Guest favorite
A welcoming exterior of a home features a covered front porch with two chairs and potted plants. Decorative shrubs and trees provide greenery, while the gray siding and white trim present a classic appearance. The front door is framed by large windows, enhancing natural light.
Home in Louisville
4.93 out of 5 average rating, 14 reviews

Germantown Gem - 3BR/2BA Home with Stock Tank Pool

KellyRating, 5 stars1 month ago
We had a great stay here while we were in town for the Oaks and Derby. Kristin was very responsive, the home was clean, comfortable, and it was a great location. Quiet but walkable to great bars and restaurants. We really enjoyed our stay!
Top guest favorite
An outdoor space is arranged with several white chairs and a table atop a striped rug. String lights illuminate the area, bordered by a wooden fence and greenery. A grill is covered and positioned beside the seating, enhancing the inviting atmosphere.
Home in Prospect
5 out of 5 average rating, 108 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

CarlaRating, 5 stars3 days ago
Nicole was, without a doubt, the best host I’ve ever had. From the moment we arrived, we were greeted with thoughtful touches thoughtfully placed throughout the home—each one clearly personalized with our family in mind. It felt less like a rental and more like staying at a close friend’s house. The bed was incredibly comfortable, and the entire home was spotless. Nicole’s attention to detail and genuine hospitality made our stay truly special. I would wholeheartedly recommend this rental to anyone looking for a warm, welcoming, and memorable experience.
Top guest favorite
A vibrant dining area features a circular table surrounded by a deep red upholstered couch. Light-colored cabinetry holds glasses and dishware, while blue and green accents complement the space. Bright windows with patterned curtains allow natural light to fill the room.
Home in Prospect
5 out of 5 average rating, 16 reviews

CIRCO LOCO - uNCommon Stay

KatieRating, 5 stars6 days ago
We had an amazing stay! The listing was even better than the photos presented… the decor was fabulous, the furnishings were such high quality, and the listing had everything we needed for our stay. Our hosts were very responsive and answered any questions so quickly. The neighborhood has great restaurants, cute little shops, and three different swimming pools to choose from… all walkable! My children said it was “better than the beach”! They even have a common work space in the floor below the unit, which was great for when I needed to work and have some quiet. Definitely 10/10 recommend!

Weekly house rentals

Guest favorite
The exterior of a recently renovated shotgun-style house features a welcoming blue front door and a small porch with a black railing. Light gray brick accents are complemented by traditional white trim. Nearby trees provide natural shade in the front yard.
Home in Germantown
4.94 out of 5 average rating, 123 reviews

Spruced-Up Shotgun, Steps to Logan St Market

KellyRating, 5 stars3 weeks ago
The house was perfect for what we needed. It's located on a quiet block, and the back parking was a great addition. The house was clean and had all the amenities we needed! If we find ourselves back in the area, we would stay here again.
Guest favorite
A charming cottage with a dark exterior showcases an inviting entrance. Steps lead to a covered porch, adorned with planters. Lush greenery and flower beds frame the house, enhancing the serene atmosphere of the peaceful neighborhood.
Home in Louisville
4.93 out of 5 average rating, 104 reviews

Quiet Neighborhood-Close to Expo, Churchill Downs!

ChristinRating, 5 stars1 week ago
Such a cute cottage in a quiet neighborhood that we felt safe in. Great place with plenty of space for our four teenagers! Nice kitchen table for playing games at night. Exceptionally clean with quality linens on the beds. Nice minimal decorations with beautiful furniture in the living room. Fenced in back yard. Nice area to park under the car port or out front so you’re not parked on the street. Everything was just as described. Quiet, friendly neighborhood. The host was very proactive and quick to respond. They even turned on the porch light for us bc I told her we were arriving late on arrival day. These small gestures are very much noticed and appreciated. We would definitely stay here again! Highly recommend! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favorite
An inviting living area features a modern grey sofa and armchair positioned on a plush area rug. Natural light enters through skylights and large windows, illuminating a kitchenette with stainless steel appliances and a dining space. Open shelving offers additional storage.
Home in Old Louisville
4.93 out of 5 average rating, 192 reviews

Beautiful space with a garage.

JasonRating, 5 starstoday
Everything was as advertised. Instructions were clear and complete. Host was responsive with questions. Neat place to stay for a few days. Garage can be tricky to get into with the tight alleyway if you have a larger vehicle as the host will tell you.
Top guest favorite
A bright living room features a dark tufted sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, and a large flat-screen TV is mounted above a white mantel. Two armchairs are positioned near a window, with natural light flowing into the space.
Home in Louisville
4.94 out of 5 average rating, 403 reviews

DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT

ChloeRating, 5 stars1 week ago
We had a great stay for a long weekend of exploring Louisville and the Bourbon Trail. We would definitely recommend this place. It is centrally located and was more than enough space for two couples.
Top guest favorite
The exterior of a charming shotgun house is visible, featuring a welcoming front porch with seating. Landscaping includes flower beds and small shrubs. A wooden fence borders the front yard, while a pathway leads to the entrance, creating an inviting approach to the home.
Home in Louisville
4.97 out of 5 average rating, 229 reviews

Charming Shotgun Style Home, Great Location

MarciaRating, 5 stars1 week ago
We really enjoyed the house; from the convenient location, to the clean, comfortable and quiet home, our stay was very pleasant. The kitchen was well equipped, the beds were comfortable and there is a general relaxed and cozy atmosphere that we enjoyed. Thank you for providing a thoughtfully appointed and friendly spot to stay.
Guest favorite
The exterior of the home features a sleek, dark blue facade with white trim around the windows and door. A welcoming floral wreath adorns the front door. Lush landscaping with rocks, plants, and a well-kept lawn enhances the charming entrance.
Home in Louisville
4.94 out of 5 average rating, 290 reviews

Louisville's Central "Lilly Pad"

BlakeRating, 5 stars5 days ago
Thanks for another great stay! Will be back soon!
Guest favorite
A living room features a modern grey sofa adorned with an orange throw, positioned near a wooden entertainment unit and a wall-mounted television. An acoustic guitar stands next to a light wood accent chair, while a vibrant landscape painting decorates the wall above an ornate fireplace.
Home in Louisville
4.95 out of 5 average rating, 267 reviews

Kentucky Hug: A Modern Shotgun for Bourbon Elites

PrestonRating, 5 stars1 month ago
Perfect house in the perfect location. The house has a lot of restaurants and bars in walking distance and is a short drive to everything else. It also had the perfect little backyard for our dogs to run around. Highly recommend.
Top guest favorite
A welcoming entrance is framed by a wooden gate, leading to a landscaped backyard featuring raised flower beds with vibrant flowers. A Tesla charging station is visible near the stone steps, surrounded by lush greenery that enhances the inviting outdoor space.
Home in Original Highlands
5 out of 5 average rating, 47 reviews

Stylish NULU | Highlands Vacation Rental

EmRating, 5 stars1 month ago
We stayed here for the Kentucky Derby and it was the absolute perfect spot. Close enough to Churchill Downs that we easily ubered there but far enough away to be nestled in a peaceful and quiet neighborhood. The house was GORGEOUS. The attention to detail-from the coffee maker options, hand blender, high quality shampoos and conditioners, nice hair dryer, Derby-esque wall decor, dimmable lighting, furniture, security of the door locks, etc. We absolutely loved it here. Picture perfect.

Private house rentals

Guest favorite
A stylish living room features a marble fireplace with decorative items above it. A wooden coffee table sits on a soft area rug, while a dark gray sofa and a classic wooden chair provide seating. Large windows offer natural light and views of greenery outside.
Home in Louisville
4.97 out of 5 average rating, 29 reviews

Tate House Vida Smith Collection

KarenRating, 5 stars3 days ago
Ashli was a fantastic host. She was very responsive and accommodating. We were there for our son‘s wedding. I asked her if we could check in early and check out late and she accommodated by giving us several hours of extra time on each end of our stay. The house was beautifully decorated and clean and the beds were upper comfy. She left a special bottle of wine, snacks and even wrote me a note wishing us a wonderful time celebrating our son’s wedding! Thank you Ashli! I would definitely stay here again!
Top guest favorite
A pair of orange chairs is positioned near a small black side table, creating an inviting seating area. A tall lamp provides warm lighting, while a glass-front cabinet displays various decorative items. The wall features wooden paneling and an assortment of artwork and signs.
Home in Louisville
5 out of 5 average rating, 47 reviews

Convenient & Cozy! Close 2 it all in Louisville!

AllisonRating, 5 stars2 weeks ago
Home was exactly as described— very clean, clear instructions for check in and check out. Nice quiet neighborhood close to downtown and all the distilleries and restaurants. Would definitely stay here again.
Superhost
A bright and airy living space features a warm leather sofa with decorative pillows, complemented by a large vase of dried flowers. An artistic mural above the doorway frames the scenic views of the outdoors, while a dining area and open layout enhance the inviting atmosphere.
Home in Louisville
5 out of 5 average rating, 8 reviews

Top-Floor Riverside Retreat|Timeless Charm & Views

Dr. LeeRating, 5 stars3 days ago
Most incredible Air b n b we've ever used, truly unique, comfortable, amazing architecture and views of the water The Riverside Retreat experience undoubtedly gave us lasting memories for a lifetime We have so much appreciation for the host and their unparalleled communication Thx so so much Dr. Lee & family 💙💙
Guest favorite
The exterior of a historic house features ornate architectural details, including decorative trim and large windows that allow natural light to fill the interior. A welcoming front door leads to the entryway, surrounded by lush greenery and landscaped flower beds.
Home in Original Highlands
4.88 out of 5 average rating, 16 reviews

Central Modern House w/ King Bed + EV Charger

KaylynRating, 5 stars1 week ago
My Husband and I booked this home extremely last minute and were pleasantly surprised with both the flexibility of the host. As for the home, it was very well appointed and we felt very comfortable.
Superhost
A queen bed is adorned with a floral print coverlet in shades of blue and green. Two decorative pillows complement the bedding. A nightstand with a lamp stands beside the bed, while a small dresser provides additional storage and a stylistic accent in the room.
Home in Original Highlands
4.9 out of 5 average rating, 48 reviews

Steps to Restaurants|Shopping|Nightlife! Highlands

CharlotteRating, 5 stars5 days ago
Repeat visit, great place to stay while visiting Louisville
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 Original Highlands
4.97 out of 5 average rating, 68 reviews

Spacious & close to downtown

MaryRating, 5 stars3 weeks ago
We ( 5 adults, a 9 yr. old and 2 dogs ) came for a family wedding and stayed 4 nights. Kara’s instructions made for an easy entry with a keypad. Her home was clean and comfortable beyond our expectations. The kitchen was well stocked and all appliances worked well for our varied needs. We also used the convenient washer and dryer provided for us. The bedrooms were spacious and beds were very comfortable. Room darkening curtains for all the windows were nice. An abundance of extra sheets, pillows and blankets in all the closets. Bathrooms were equipped with plenty of towels and shampoos, soaps etc. The backyard is fenced in with plenty of seating and a barbecue grill. The house is on a quiet street and there was always room to park our 2 cars in front of the house. Pleasant neighborhood for our many walks with a variety of restaurants a few short blocks away. Kara was a very friendly and responsive host. We highly recommend this home and would definitely stay here again. Mary
Superhost
A modern kitchen is presented, featuring a central island with a polished wood countertop. Four metal bar stools are positioned around the island. Stainless steel appliances, including a refrigerator and stove, are visible along with cabinetry. Light colored walls enhance the airy feel of the space.
Home in Original Highlands
4.88 out of 5 average rating, 80 reviews

2BR Oasis in walkable Original Highlands

LindsayRating, 5 stars1 week ago
Thank you, Stam for being such a welcoming host and for checking in to ensure everything was going smoothly. The check-in process was seamless, and the place itself was great. The location was excellent, within walking distance to breakfast spots and shops, and just 8–15 minutes from everything we wanted to see. Parking was easy and convenient, and the neighborhood was peaceful with friendly locals out walking their dogs. I would stay here again!
Top guest favorite
The exterior of the historic 1890 shotgun-style home features yellow siding, large windows with sheer curtains, and a welcoming front door. Lush greenery and flowers frame the entrance, complemented by stone steps leading up to the door, creating an inviting atmosphere.
Home in Original Highlands
5 out of 5 average rating, 37 reviews

My Old Kentucky Home in trendy area of Louisville!

EricRating, 5 stars1 month ago
My Old Kentucky Home is a very fitting name for this property. Spectacular old house that has been tastefully update & decorated, free of clutter & made us feel right at home. The property was exceptionally clean & it is obvious the hosts took pride in the place. Jenny & Brent were amazingly fast to respond & even reached out to make sure we were good. They went above & beyond when the power was out, even though it was out of their control. We chose this place based on proximity to dining & shopping but would recommend it for a peaceful getaway. Quiet neighborhood, great outdoor space & space to lounge & chill inside ... & feel like you are at home. Highly recommended!

Quick stats about house rentals in Original Highlands, Louisville

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$8,363 GYD before taxes and fees

  • Total number of reviews

    5.8K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore