Vacation rentals in Original Highlands, Louisville

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Top-rated vacation rentals in Original Highlands, Louisville

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

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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.

Sep 1 – 8

R1,687 ZAR per night

Guest favorite

Townhouse in Louisville

4.95 out of 5 average rating, 215 reviews

Louisville Charm: Walk to it All! Central & Quaint

Welcome to the charm and character of Louisville! WALKING DISTANCE to everything you can enjoy. You will be right off the main strip of Frankfort Ave near Nulu. Less than a 5min walk to local breweries, coffee shops, restaurants, bars +more! Your experience includes: -queen suite -clawfoot tub shower combo -rollaway twin bed -stocked kitchen w/blender & toaster -AT&T fiber wifi -wine fridge -smart tv -desk workstation -Levoit air purifier -coffee & tea -happy live plants -inviting neighborhood

Dec 30 – Jan 6

R2,316 ZAR 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 25 – Sep 1

R2,160 ZAR per night

Superhost

Apartment in Highlands

4.84 out of 5 average rating, 129 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.

Aug 29 – Sep 5

R2,124 ZAR 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.

Dec 23 – 30

R2,080 ZAR per night

Guest favorite

Guesthouse in Louisville

4.98 out of 5 average rating, 243 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.

Aug 26 – Sep 2

R2,058 ZAR 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 21 – 28

R1,268 ZAR per night

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 662 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 9 – 16

R1,686 ZAR per night

Guest favorite

Home in Highlands

4.89 out of 5 average rating, 107 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

Jul 22 – 29

R1,834 ZAR 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.

Aug 23 – 30

R1,659 ZAR 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!

Mar 21 – 28

R2,206 ZAR per night

Guest favorite

Home in Highlands

4.91 out of 5 average rating, 199 reviews

PRIME HIGHLANDS LOCATION!

A well appointed, newly remodeled house in a prime location in the heart of Highlands with restaurants, bars, coffee shops and shopping, all within a couple of minutes walk. Churchill Downs is a short 10 minute drive, and Downtown is a couple of minutes drive.

Jul 3 – 10

R1,967 ZAR per night