House vacation rentals in Original Highlands, Louisville

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Top-rated house rentals in Original Highlands, Louisville

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Guest favorite

Home in Louisville

4.95 out of 5 average rating, 228 reviews

Highlands Haven Cottage

This luxurious and charming 1 bedroom home in the prime area of Louisville and The Highlands, is walking distance to the Douglass Loop area of shops and dinning, the Bardstown Rd corridor of shops and dinning and more starts at The Loop, as well as the locally famous Farmers Market on Saturday mornings! This 800 sf fully furnished home features 1 bedroom, 1 bath, a large & bright family room, and a fully outfitted kitchen, is literally minutes to lots of local amenities, dining, shopping, etc!

Nov 5 – 12

ﺩ.ﺇ495 per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 111 reviews

Highlands Bishop Cottage-Walkable

Walkable Highlands Cottage in the Irish Hills neighborhood. Newly renovated with charm! Close to NULU (.5 mi), Butchertown (.6 mi), downtown (1 mi). Just 4 mi to the Yum Center, 5 mi to the Expo Center, 5.2 mi to Churchhill Downs, and 5.7 mi to the airport. Walkable to breweries, restaurants, parks and Cave hill Cemetery. You can even view the bridge over Ohio River from the end of the street. One on property parking spot off the alleyway with additional street parking on side streets.

Aug 31 – Sep 7

ﺩ.ﺇ503 per night

Guest favorite

Home in Louisville

4.98 out of 5 average rating, 336 reviews

Velo Studio Flat / Paristown Pointe / Highlands

Next to the The Highlands, this bike friendly house is in Paristown Pointe with great restaurants, Louisville Stoneware & an easy walk to Baxter & Bardstown Rd for nightlife. A clean, comfortable & stylish home in a quiet area. Four 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.

Apr 1 – 8

ﺩ.ﺇ542 per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 224 reviews

The Bourbon Belle- 1bd/2ba Home in Germantown!

The Bourbon Belle is a newly renovated historic shotgun home in the heart of Louisville's Germantown neighborhood. Lots of natural light and tall ceilings make your stay feel comfy and warm just like home. Sleeps 4 comfortably and has 1.5 bathrooms. W/D. 2 Smart 55" TVs. High speed internet. EV Charging Station @ Full Stop Cafe across the street. Centrally located, close to Downtown, U of Louisville, KY Fair &Expo Center, Louisville Airport, and only 3.2 miles away from Churchill Downs.

Dec 8 – 15

ﺩ.ﺇ389 per night

Guest favorite

Home in Louisville

4.89 out of 5 average rating, 123 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*

Oct 4 – 11

ﺩ.ﺇ651 per night

Guest favorite

Home in Louisville

4.89 out of 5 average rating, 141 reviews

*Gorgeous common space w/ sunlight & powder area!*

The Highlands Hideout is an 1800 square foot, lofted, tranquil space with endless natural light and a wide open first floor area; perfect for enjoying time with friends, family, and/or loved ones! Once you step outside you are immediately immersed in Louisville’s most popular/historic neighborhood, the Highlands, as you’re a mere 150 feet from Bardstown Road. Make the Hideout your space to relax and recover after taking in all the food, shops, and bars that make Louisville unique.

Aug 31 – Sep 7

ﺩ.ﺇ527 per night

Guest favorite

Home in Louisville

4.91 out of 5 average rating, 117 reviews

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

Sep 7 – 14

ﺩ.ﺇ453 per night

Guest favorite

Home in Louisville

4.87 out of 5 average rating, 468 reviews

The Crescent Cottage

The Crescent Cottage is the perfect getaway spot. It is in the heart of the city behind Eastern Parkway! If you stay here you are walking distance to great parks, coffee, and restaurants. The cottage is a short 10 minute drive from the airport. Nestled between both major universities, Bellarmine university and the University of Louisville. The cottage is 100+ years old and is newly renovated by yours truly—Ben! We can’t wait to meet you and have you stay here.

Nov 2 – 9

ﺩ.ﺇ360 per night

Guest favorite

Home in Louisville

4.96 out of 5 average rating, 269 reviews

Garden House - Nulu

Don't just rent an Airbnb . . . experience this Award winning home, known as the Garden House. It is the most unique place to stay in the Butchertown, NuLu area. Very private yet in the heart of the city. The Garden House is always surrounded by green space. Relax on the front porch, or grill out with friends in the private garden. Perfect for a romantic weekend, experiencing the Bourbon Trail, going to Churchill Downs or a concert.

Aug 6 – 13

ﺩ.ﺇ652 per night

Guest favorite

Home in Louisville

4.97 out of 5 average rating, 261 reviews

Historic Parsonage in heart of NuLu action

Located in a lovingly renovated 1843 church, this small apartment boasts a queen-size bed, full bathroom, kitchenette with table for 3, and comfy sofa. You'll be in the middle of all Market Street has to offer — steps from Rabbit Hole Distillery, Nouvelle Wine Bar, Garage Bar, and tons more. A 10-minute ride from the airport, you'll be half a mile from Slugger Field, and 1 mile from the YUM! and Convention Centers.

Oct 3 – 10

ﺩ.ﺇ499 per night

Guest favorite

Home in Louisville

4.98 out of 5 average rating, 277 reviews

Urban spot close to breweries, distilleries & more

Welcome to "The Hamilton House" Air B&B nestled between the Highlands and Nulu in the Paristown neighborhood. This amazing Louisville getaway boasts an unbeatable outdoor experience. In addition, you will be be within walking distance of excellent dining, breweries, and entertainment and within easy driving distance to all that downtown Louisville offers as well.

Jul 22 – 29

ﺩ.ﺇ536 per night

Guest favorite

Home in Louisville

4.97 out of 5 average rating, 297 reviews

The Highlands Condo/Roof Deck

Our brand new renovated 1 BR condo is located in a famous Highlands’ neighborhood. Conveniently located about 5-8 minutes from Churchill Downs, KFC Yum Center, Cardinal Stadium, Convention Center, Center for the Arts, Downtown Distilleries, Nulu& Germantown area, 12 minutes from the airport. Walking distance to many great restaurants, bars, shops , and parks.

Mar 12 – 19

ﺩ.ﺇ402 per night