Vacation rentals in Original Highlands, Louisville

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Top-rated vacation rentals in Original Highlands, Louisville

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Guest favorite

Apartment in Louisville

4.94 out of 5 average rating, 231 reviews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Dec 9 – 16

ﺩ.ﺇ530 per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 106 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Feb 10 – 17

ﺩ.ﺇ322 per night

Guest favorite

Home in Germantown

4.94 out of 5 average rating, 119 reviews

Great Location in Germantown! Private Parking!

Shotgun Rye is ready to host your stay in Louisville! Located close to everything cool in Germantown and Highlands area! People visit for Bourbon Tours, Ky Derby, Conventions, Expo Ctr, UL graduations and sporting events, live music and so much more! Completely remodeled with all the modern conveniences & a comfortable, casual touch. But with so much to see and do in Louisville you’ll load up your itinerary with unforgettable experiences. Great location walk to bars, restaurants and shopping!

Aug 10 – 17

ﺩ.ﺇ413 per night

Superhost

Apartment in Highlands

4.84 out of 5 average rating, 128 reviews

Highly Rated Highlands Retreat- Central Location

NEW LISTING! 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.

Jul 29 – Aug 5

ﺩ.ﺇ384 per night

Guest favorite

Home in Highlands

4.91 out of 5 average rating, 116 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.

Apr 5 – 12

ﺩ.ﺇ397 per night

Guest favorite

Guesthouse in Louisville

4.98 out of 5 average rating, 241 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.

Oct 13 – 20

ﺩ.ﺇ393 per night

Guest favorite

Guesthouse in Germantown

4.95 out of 5 average rating, 220 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

Jul 19 – 26

ﺩ.ﺇ243 per night

Guest favorite

Apartment in Louisville

4.95 out of 5 average rating, 355 reviews

Sunny Clifton Loft

Recently renovated studio apartment with loads of natural light, steps from award-winning local restaurants, bakeries, bars, and housed above our independent record store. We do our best to AirBnB ethically & responsibly.. Revenue from this unit helps to 1) keep on-site residential rents affordable & increase-free 2) maintain the historic building & protect it from outside development while 3) help us steer our future as a brick and mortar independent business.

May 27 – Jun 3

ﺩ.ﺇ360 per night

Guest favorite

Guest suite in Louisville

4.98 out of 5 average rating, 536 reviews

Eco+ guest suite in the center of all the fun

Hip modern amenities meet historic home in Shelby Park. A quick drive to everything in the urban core - Downtown, Nulu, Old Louisville, the Highlands, Germantown, and more. Easy access to the airport, to boot! We are pet friendly home, but require your pets be registered on the booking. We want your pets (and ours) to be as safe and comfortable as you are, and the fee covers additional costs to complete allergen level sanitization.

Oct 13 – 20

ﺩ.ﺇ313 per night

Guest favorite

Bungalow in Germantown

4.96 out of 5 average rating, 273 reviews

Charming Bourbon Bungalow - 1 Mile from Downtown!

You will love this quaint Germantown house located 2 miles from almost anywhere you would want to be in the city! Two bedrooms and one bath await you, along with a full kitchen, large living space, and spacious back yard. Close to many great restaurants, downtown attractions, the Highlands, Churchill Downs, the riverfront, and many great parks. Don't wait--book now!

Feb 28 – Mar 7

ﺩ.ﺇ421 per night

Guest favorite

Guesthouse in Germantown

5.0 out of 5 average rating, 156 reviews

*BRAND NEW* Gem of Germantown Private Derby Suite

- Heart of trendy Germantown neighborhood - ~ 1 block: hip restaurants, bars, cafes, boutiques, grocery/liquor store - Keyless entry, 2nd floor unit (**15 stairs to the door**) above a garage with a patio - Quiet street, 5-10 minutes from all of Louisville's top attractions - Free street parking

Jun 4 – 11

ﺩ.ﺇ484 per night

Guest favorite

Guesthouse in Louisville

4.99 out of 5 average rating, 363 reviews

Highlands - Elegant Calm Clean & Green - Walkable

New, Elegant and Calm - Ideally located Carriage House in the Highlands - Cherokee Triangle – 2 Bedrooms with 3 beds (1 queen, 2 twins) / 1 bath (Partitioned for multiuse) - Includes new appliances, all furnished and nicely decorated - TVs / Cable / Super fast Internet / Washer / Dryer / Deck.

Aug 26 – Sep 2

ﺩ.ﺇ462 per night