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House vacation rentals in Original Highlands, Louisville

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Top-rated house rentals in Original Highlands, Louisville

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

Guest favorite
Home in Germantown
Whole House in Germantown w/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 13 – 20
$97 per night
4.95 out of 5 average rating, 111 reviews
Guest favorite
Home in Highlands
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.
Nov 1 – 8
$94 per night
4.92 out of 5 average rating, 102 reviews
Guest favorite
Home in Highlands
*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.
Jul 27 – Aug 3
$122 per night
4.9 out of 5 average rating, 128 reviews

Popular amenities for Original Highlands, Louisville house rentals

House rentals with a pool

Superhost
Home in Louisville
Sleeps 16, Highlands Area, Heated Pool, Hot tub
Dec 25 – Jan 1
$884 per night
4.95 out of 5 average rating, 128 reviews
Guest favorite
Home in Louisville
"The Eagles Nest" 3-4 bedroom River house.
Oct 20 – 27
$736 per night
5.0 out of 5 average rating, 36 reviews
Guest favorite
Home in Louisville
Entire House in The Highlands. Private Pool.
Oct 21 – 28
$361 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Home in Louisville
Vintage Bungalow with Pool, Near Everything!
Feb 13 – 20
$153 per night
4.92 out of 5 average rating, 12 reviews
Guest favorite
Home in Louisville
Louisville Getaway. Memories made here!
Mar 4 – 11
$625 per night
4.96 out of 5 average rating, 95 reviews
Superhost
Home in Louisville
HUGE 6 BR home w/ 9 beds! Mins from expo/downtown
Jan 29 – Feb 5
$306 per night
4.81 out of 5 average rating, 31 reviews
Guest favorite
Home in Clarksville
10 Min to Lou | Huge Hot Tub | Awesome Backyard
Jan 19 – 26
$240 per night
5.0 out of 5 average rating, 34 reviews
Home in Louisville
Wilder Park Peacock House - 2 bedrm + Pool
Jun 24 – Jul 1
$149 per night
4.93 out of 5 average rating, 27 reviews
Guest favorite
Home in Louisville
Central Germantown 3 BR Shotgun w/ Stock Tank Pool
Sep 24 – Oct 1
$407 per night
4.83 out of 5 average rating, 6 reviews
Guest favorite
Home in Jeffersonville
Cozy Neighborhood Home - 10 min to Louisville!
Apr 16 – 23
$105 per night
4.93 out of 5 average rating, 27 reviews
Home in Louisville
Pool , Hot tub , Sauna-3 bedrooms, 2 full bath
Jul 15 – 22
$334 per night
4.71 out of 5 average rating, 86 reviews
Home in Jeffersonville
Downtown Derby Classic- Heated Pool, Firepit,Grill
Nov 15 – 22
$415 per night
4.78 out of 5 average rating, 36 reviews

Weekly house rentals

Guest favorite
Home in Butchertown
Butchertown’s Historic Shantyboathouse
Jan 29 – Feb 5
$336 per night
5.0 out of 5 average rating, 151 reviews
Guest favorite
Home in Louisville
Walk to All! Historic District Townhouse 2.5 baths
Oct 24 – 31
$196 per night
4.91 out of 5 average rating, 179 reviews
Guest favorite
Home in East Market District
Garden House - Nulu
Aug 19 – 24
$196 per night
4.96 out of 5 average rating, 257 reviews
Guest favorite
Home in Germantown
Germantown gem w/ private parking & fenced in yard
Mar 24 – 29
$137 per night
4.91 out of 5 average rating, 105 reviews
Guest favorite
Home in Louisville
The "Kentucky Hug" - Downtown, Highlands, EXPO
Dec 4 – 11
$160 per night
4.92 out of 5 average rating, 101 reviews
Guest favorite
Home in Louisville
Lovely Home Steps to Restaurant Row
Nov 12 – 19
$136 per night
4.94 out of 5 average rating, 535 reviews
Guest favorite
Home in East Market District
House of Black & White|Hot Tub|Fire Pit|King Bed
Jan 6 – 13
$222 per night
4.94 out of 5 average rating, 197 reviews
Guest favorite
Home in Louisville
Urban spot close to breweries, distilleries & more
Apr 28 – May 3
$273 per night
4.98 out of 5 average rating, 267 reviews
Superhost
Home in Louisville
Prime Highlands Location - 500ft fro. Midcity Mall
Nov 20 – 27
$148 per night
4.86 out of 5 average rating, 133 reviews
Guest favorite
Home in Louisville
Velo Studio Flat / Paristown Pointe / Highlands
Dec 20 – 27
$125 per night
4.98 out of 5 average rating, 330 reviews
Guest favorite
Home in Louisville
Indulge in the Highlands*Steps to NuLu & Downtown
Jun 5 – 12
$216 per night
4.91 out of 5 average rating, 246 reviews
Superhost
Home in Louisville
Lucky in Limerick Carriage Company
May 31 – Jun 7
$79 per night
4.9 out of 5 average rating, 551 reviews

Private house rentals

Guest favorite
Home in Germantown
The Crescent Cottage
Nov 2 – 9
$84 per night
4.88 out of 5 average rating, 451 reviews
Guest favorite
Home in Louisville
The River's Edge Oasis, close to downtown
Aug 14 – 21
$260 per night
4.94 out of 5 average rating, 145 reviews
Guest favorite
Home in Louisville
Sip Bourbon on the Custom Brick Patio at Heartpine and Soul
Aug 22 – 29
$211 per night
4.96 out of 5 average rating, 185 reviews
Superhost
Home in Louisville
NuLu Private Home|Backyard|Parking
Apr 11 – 18
$166 per night
4.86 out of 5 average rating, 124 reviews
Guest favorite
Home in Highlands
Eclectic Historic House in the Highlands
Apr 12 – 19
$278 per night
4.96 out of 5 average rating, 219 reviews
Guest favorite
Home in Old Louisville
Downtown Louisville 2.5 mi to DERBY
Mar 14 – 21
$116 per night
4.98 out of 5 average rating, 193 reviews
Superhost
Home in Louisville
Adorable 2 BR - WALK to The Kentucky Derby!
May 22 – 29
$83 per night
4.86 out of 5 average rating, 191 reviews
Guest favorite
Home in Louisville
Cozy home in Louisville with convenient location!
Aug 12 – 19
$110 per night
4.9 out of 5 average rating, 159 reviews
Guest favorite
Home in Louisville
Shelby Manor
Apr 3 – 10
$94 per night
4.87 out of 5 average rating, 187 reviews
Guest favorite
Home in New Albany
The Green House in Downtown
Aug 22 – 29
$99 per night
4.98 out of 5 average rating, 130 reviews
Superhost
Home in Louisville
"Blue Grass" Pool Table Retreat - Plush Comfort
Jul 26 – Aug 2
$236 per night
4.93 out of 5 average rating, 115 reviews
Superhost
Home in East Market District
NuLu|HotTub|KingBed|FirePit|BBQ|70"TV|Derby!
Aug 12 – 19
$548 per night
4.91 out of 5 average rating, 196 reviews

Quick stats about house rentals in Original Highlands, Louisville

Total rentals

60 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

4.6K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore