House holiday rentals in Original Highlands, Louisville

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Popular amenities for house rentals in Original Highlands, Louisville

House rentals with a pool

Top guest favourite
Home in Mount Washington
5 out of 5 average rating, 47 reviews

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

KathyRating, 5 stars1 day ago
This home was fantastic. We especially loved the shed with pickleball, shuffleboard, bags, etc. and the pool and hot tub. The home had plenty of room, bedrooms and bathrooms for our family of 9. The well-stocked coffee bar, laundry facilities and the nice bathrooms especially stood out. We enjoyed having soap dispensers available at every sink including the kitchen. Dishwasher pods and laundry pods were provided, unlike many other air bnbs we’ve stayed in. The location was great as we did Churchill Downs, Louisville Slugger Museum, many distilleries and the Horse Park at Lexington. No issues whatsoever but Kaelie stayed in touch throughout our stay. We would highly recommend this property.
Top guest favourite
Home in Prospect
5 out of 5 average rating, 8 reviews

NEW Pet Friendly, Horse Country, Bourbon, Downtown

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
Home in Louisville
4.84 out of 5 average rating, 25 reviews

Near Bourbon Trail, expo, 3 beds, off Outerloop

ChristieRating, 5 stars4 weeks ago
Stayed just one night when in town for a high school graduation. Very close to the KY expo area. Quiet neighborhood.
Top guest favourite
Home in Louisville
4.97 out of 5 average rating, 34 reviews

Highlands Oasis- Summer and Winter Retreat

JacksonRating, 5 stars2 months ago
A wonderful home hosted by wonderful people. I can’t thank Amy and Carol enough for being incredible hosts and opening their home to us. Would certainly recommend this to anyone considering staying in the area!
Top guest favourite
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 favourite
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 favourite
Home in Prospect
5 out of 5 average rating, 107 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

BetsieRating, 5 stars2 weeks ago
Amazing stay. Nicole was super responsive and over the top helpful with info and recommendations. The house was beautiful. Everything exceeded our expectations. Looking forward to coming back !
Top guest favourite
Home in Prospect
5 out of 5 average rating, 16 reviews

CIRCO LOCO - uNCommon Stay

KatieRating, 5 stars2 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

Top guest favourite
Home in Louisville
4.99 out of 5 average rating, 149 reviews

"The Brook" - Louisville

JulieRating, 5 stars6 days ago
Comfortable home in great neighbourhood. Had everything we needed for our stay. Close to everything. Good communication from Jordan.
Guest favourite
Home in Louisville
4.93 out of 5 average rating, 239 reviews

Fully Renovated 1960s Urban Chic Deer Park Retreat

KallieRating, 5 stars2 weeks ago
We loved staying at this house! It was decorated nicely and had all the amenities we needed. The beds were comfortable and there was plenty of space. The patio out back was great for family game nights! We walked to 80/20, which was a great restaurant close by. The house is in a great location, as we were also 6 minutes from the zoo, which my son loved! We would definitely stay at this place again!
Guest favourite
Home in Germantown
4.94 out of 5 average rating, 123 reviews

Spruced-Up Shotgun, Steps to Logan St Market

KellyRating, 5 stars2 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 favourite
Home in Louisville
4.93 out of 5 average rating, 104 reviews

Quiet Neighborhood-Close to Expo, Churchill Downs!

ChristinRating, 5 stars6 days 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 favourite
Home in Original Highlands
4.93 out of 5 average rating, 15 reviews

Central Modern House w/ King Bed + EV Charger

KaylynRating, 5 stars6 days 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.
Top guest favourite
Home in Louisville
4.96 out of 5 average rating, 227 reviews

Charming Shotgun Style Home, Great Location

AlexisRating, 5 stars3 weeks ago
Loved this cute house for my family and I. Willie and Sue left a very detailed message about everything before we got there and gave their numbers incase we needed anything which I appreciated. The house was very clean and comfortable. The location is great. It’s minutes away from shopping, food, and coffee shops! We were sad to leave. We hope to be back!
Guest favourite
Home in Louisville
4.94 out of 5 average rating, 289 reviews

Louisville's Central "Lilly Pad"

BlakeRating, 5 stars1 week ago
This was a great house and very comfortable. Anthony was fantastic and easy to communicate with. Will definitely be back.
Superhost
Home in Louisville
4.89 out of 5 average rating, 207 reviews

*Walk to Churchill Downs!*Close to Expo, UL, YUM!

KathyRating, 5 stars1 month ago
Our stay at Lilly House was excellent. The house itself was clean and very inviting. We were provided with everything we needed with much more than essentials. Fredie was welcoming and made it apparent he was available for any of our needs. The location was a short drive to downtown and very assessable to everything. We would recommend staying here and appreciate the attention to details during or stay. A great, clean place to stay.

Private house rentals

Guest favourite
Home in Louisville
4.96 out of 5 average rating, 28 reviews

Tate House Vida Smith Collection

AnthonyRating, 5 stars3 weeks ago
A great place to stay with friends in a great part of town. Logistically easy to check in, clean and beautiful interior, clear directions for check in and check out, and plenty of beds and bathrooms to accommodate larger groups...There is plenty to do off Bardstown road and it served as a great homebase for the Bourbon Trail!
Guest favourite
Home in Germantown
5 out of 5 average rating, 42 reviews

~Brand new~Luxury 3BR~Walkable~Central AC~

AndreaRating, 5 stars1 week ago
I had a wonderful stay at Barbara’s Airbnb! The house is brand new, beautifully set up, and fully equipped with everything you could need. The location is great—just a few streets from restaurants and only about 10 minutes to downtown via the highway. Everything in the home feels fresh and thoughtfully chosen, from the ultra-comfy beds and bedding to the plush towels. You can tell a lot of care went into the space—there are so many little details and extras that make it feel truly comfortable. Honestly, it felt just like staying at home. Highly recommend!
Top guest favourite
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.
Guest favourite
Home in Original Highlands
4.92 out of 5 average rating, 64 reviews

PacMan! Walk to Nightlife | Restaurants | Shopping

RobRating, 5 stars6 days ago
Great location near lots of bars / restaurants and not far from downtown. Clean and comfortable rental. As described in the listing there definitely is some street noise but was not a problem for us at all.
Top guest favourite
Home in Louisville
5 out of 5 average rating, 95 reviews

Quaint Highland's Bungalow

KateRating, 5 stars1 week ago
From the spot on communication pre-arrival to the waiting hospitality basket to the immaculate and tastefully decorated home to the prompt replies to texts and emails during our stay, I can't say enough about the excellent experience we had from start to finish. We had lots of family to visit so we often were gone most of the day but returning in the evenings for a quiet moment on the beautiful front porch or backyard was heaven! Thank you John. We felt like we were your one and only guests, ever! We hope to return soon.
Superhost
Home in Original Highlands
4.88 out of 5 average rating, 80 reviews

2BR Oasis in walkable Original Highlands

LindsayRating, 5 stars6 days 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!
Guest favourite
Home in Germantown
4.91 out of 5 average rating, 88 reviews

Prime Location for Derby Weekend | Bourbon Themed!

EricaRating, 5 stars1 day ago
Shannon was a great hostess and the home was very nice. It was everything the photos promised. I played the arcade table top games, tested out the hot tub and slept hard in the bed. We ubered mostly to the Germantown restaurants and tried The Post pizza, Breakfast AF and Sarinos. We did not spend a ton of time at the home since we were out on a whiskey tour but it definitely provided what we needed. I love the decor as well.
Top guest favourite
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

    ₹3,463 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