Vacation rentals in Original Highlands, Louisville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Original Highlands, Louisville

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 105 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.

Mar 2 – 9

$76 per night

Superhost

Cottage in Germantown

4.85 out of 5 average rating, 261 reviews

Tyler Park Cottage in the Highlands

Adorable, light-filled cottage in the beloved Highlands neighborhood. An easy ten minute walk in one direction will put you on Bardstown Road, full of dining and bars, while a 15 minute walk in the other will land you in the hip Germantown-Schnitzelburg neighborhood. A short (6 minute) drive to downtown, 11 minutes to Churchill Downs. You'll find wireless internet, clean towels and sheets, basic kitchen and bathroom amenities, coffee maker, a flat screen TV with Apple TV, and keyless entry.

Oct 6 – 13

$110 per night

Guest favorite

Home in Germantown

4.95 out of 5 average rating, 117 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!

Nov 20 – 27

$97 per night

Superhost

Apartment in Highlands

4.84 out of 5 average rating, 127 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 24 – 31

$87 per night

Guest favorite

Home in Highlands

4.92 out of 5 average rating, 114 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.

Jan 13 – 20

$94 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 2 – 9

$93 per night

Guest favorite

Apartment in Louisville

4.95 out of 5 average rating, 354 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 29 – Jun 5

$85 per night

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 658 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. This newly constructed carriage house has all the amenities for any length of stay, including garage parking with room for bikes or kayaks. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

Oct 3 – 10

$79 per night

Superhost

Home in Highlands

4.89 out of 5 average rating, 105 reviews

Walk to it ALL! The Best Location!

THE MOST WALKABLE PART OF LOUISVILLE 7 minutes to the KFC Yum Center! Dedicated parking Pet Free Home Very Budget Friendly. A great VALUE. This home provides your basic necessities at a great price that very few Bnbs can beat! Our goal is to provide affordability to those traveling on a budget! Also for your enjoyment: Self Check in with Keypad Easy to follow check in instructions with photos Stocked kitchen for cooking Roku Streaming Free Wifi

Feb 22 – Mar 1

$65 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.

Sep 30 – Oct 7

$74 per night

Guest favorite

Bungalow in Germantown

4.96 out of 5 average rating, 272 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!

Aug 19 – 26

$94 per night

Guest favorite

Guesthouse in Germantown

5.0 out of 5 average rating, 155 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 1 – 8

$109 per night