Vacation Rentals in Windy Hills, KY: Compare 10+ Sites & Save

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848 Best Vacation Rentals in Windy Hills (Starting from $114)

2 Living Rooms Close 2 Shopping & Restaurants
2 Living Rooms Close 2 Shopping & Restaurants
House
Louisville, KY, USA
2.1k from Windy Hills center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

3 Bedrooms9 Guests
New to Booking
$1543
Average price / night
Check Availability
Southern Comfort with Best Location in the City
Southern Comfort with Best Location in the City
House
Louisville, KY, 40222, United States
1.1k from Windy Hills center

Dryer, Internet, Laundry, No Smoking, Outdoor Space, Patio, Washer

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$571
Average price / night
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Modern cozy residential home local experience
Modern cozy residential home local experience
House
Louisville, KY, USA
3.1k from Windy Hills center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$537
Average price / night
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Historic Woodlawn Park Home
Historic Woodlawn Park Home
House
Louisville, KY, 40207, United States
1.1k from Windy Hills center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms10 Guests
9.6

Exceptional

18 reviews

$320
Average price / night
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Luxe Lyndon Home Less Than 11 Mi to Dtwn Louisville!
Luxe Lyndon Home Less Than 11 Mi to Dtwn Louisville!
House
Louisville, KY, USA
3.5k from Windy Hills center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$354
Average price / night
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Elegant, newly remodeled 3-bedroom house in Louisville available for Derby week!
Elegant, newly remodeled 3-bedroom house in Louisville available for Derby week!
House
Louisville, KY, 40207, United States
1.3k from Windy Hills center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$3482
Average price / night
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Charming Louisville Retreat with Patio and Fireplace!
Charming Louisville Retreat with Patio and Fireplace!
House
Louisville, KY, USA
3.7k from Windy Hills center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms11 Guests
9.3

Superb

3 reviews

$498
Average price / night
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Home in prime location near Louisville attractions
Home in prime location near Louisville attractions
House
Louisville, KY, 40207, United States
1.5k from Windy Hills center

AC, Heater, Internet, Kitchen, No Smoking, Toys

1 Bedroom4 Guests
New to Booking
$212
Average price / night
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Louisville Retreat with Deck about 11 Mi to Downtown!
Louisville Retreat with Deck about 11 Mi to Downtown!
House
Louisville, KY, USA
3.7k from Windy Hills center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$332
Average price / night
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15 min. to Downtown; 17 min. to Expo Center; 18 min. to Churchill Downs-Derby
15 min. to Downtown; 17 min. to Expo Center; 18 min. to Churchill Downs-Derby
House
Louisville, KY, 40207, United States
1.7k from Windy Hills center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms10 Guests
9.4

Superb

12 reviews

$623
Average price / night
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Charming 4-Bed Home with Modern Touches & Porch
Charming 4-Bed Home with Modern Touches & Porch
House
Louisville, KY, USA
4.9k from Windy Hills center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$803
Average price / night
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Cozy house in the heart of the city!
Cozy house in the heart of the city!
House
Louisville, KY, 40222, United States
2.0k from Windy Hills center

AC, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$357
Average price / night
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The B
The B
Apartment
Windy Hills, Louisville, Kentucky, USA
4.9k from Windy Hills center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

2 Bedrooms7 Guests
9.2

Superb

89 reviews

$150
Average price / night
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Charming home in Louisville for Derby!
Charming home in Louisville for Derby!
House
Louisville, KY, 40207, United States
2.1k from Windy Hills center

AC, Dryer, Heater, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$1517
Average price / night
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Historic Peterson Mansion - Savor Life and Rest with Friends!
Historic Peterson Mansion - Savor Life and Rest with Friends!
House
Louisville, KY, USA
5.6k from Windy Hills center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

6 Bedrooms18 Guests
New to Booking
$7497
Average price / night
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4-bedroom Remodeled St Matthews Cape Cod
4-bedroom Remodeled St Matthews Cape Cod
House
Louisville, KY, 40207, United States
2.1k from Windy Hills center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$1291
Average price / night
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Park Carriage House Rest & Explore with Hollyhock
Park Carriage House Rest & Explore with Hollyhock
House
Louisville, KY, USA
5.6k from Windy Hills center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms12 Guests
9.1

Superb

30 reviews

$272
Average price / night
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Charming 4-bedroom house with WiFi and AC in Louisville.
Charming 4-bedroom house with WiFi and AC in Louisville.
House
Louisville, KY, 40222, United States
2.2k from Windy Hills center

AC, Dryer, Internet, Laundry, No Smoking, Washer

4 Bedrooms6 Guests
New to Booking
$2321
Average price / night
Check Availability
Louisville Derby Special! 2 Queen Bdr
Louisville Derby Special! 2 Queen Bdr
Apartment
Louisville, KY, USA
6.3k from Windy Hills center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$935
Average price / night
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Charming Kentucky home! Walking distance to bars and restaurants.
Charming Kentucky home! Walking distance to bars and restaurants.
House
Louisville, KY, 40207, United States
2.2k from Windy Hills center

AC, Heater, Internet, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1583
Average price / night
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1 Block to Mellwood Modern Apt by Shops and Dining!
1 Block to Mellwood Modern Apt by Shops and Dining!
Apartment
Louisville, KY, USA
6.4k from Windy Hills center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms4 Guests
New to Booking
$201
Average price / night
Check Availability
Beautiful 4 BR, 4.5 Bath, Executive Home w In Ground Pool & Handicap Accessible!
Beautiful 4 BR, 4.5 Bath, Executive Home w In Ground Pool & Handicap Accessible!
House
Louisville, KY, 40222, United States
2.3k from Windy Hills center

AC, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms10 Guests
9.8

Exceptional

31 reviews

$1169
Average price / night
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Heart of ST Mathews
Heart of ST Mathews
House
Louisville, KY, 40207, United States
2.3k from Windy Hills center

Dryer, Extra Bed, Internet, Laundry, No Smoking, Outdoor Space, Washer

4 Bedrooms7 Guests
New to Booking
$155
Average price / night
Check Availability
Cozy Home in East Louisville!
Cozy Home in East Louisville!
House
Louisville, KY, 40222, United States
2.4k from Windy Hills center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms10 Guests
New to Booking
$114
Average price / night
Check Availability
Make Derby Memories in this Charming 4-bedroom house located in St. Matthews!
Make Derby Memories in this Charming 4-bedroom house located in St. Matthews!
House
Louisville, KY, 40207, United States
2.4k from Windy Hills center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms14 Guests
New to Booking
$2323
Average price / night
Check Availability
Derby Destination (20 Minutes to Churchill Downs): Lovely House and Garden
Derby Destination (20 Minutes to Churchill Downs): Lovely House and Garden
House
Louisville, KY, 40241, United States
2.4k from Windy Hills center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$4155
Average price / night
Check Availability
Kentucky Derby Rental. Premier location,  fantastic classic home
Kentucky Derby Rental. Premier location, fantastic classic home
House
Louisville, KY, 40222, United States
2.4k from Windy Hills center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$685
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Windy Hills.

Stay Near Windy Hills's Top Attractions

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Windy Hills Vacation Rentals on the Map

Frequently Asked Questions

You can explore 848 verified vacation rentals in Windy Hills. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Windy Hills vary depending on the season, property size, and location. Rates typically start from around $114 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Windy Hills include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Windy Hills welcome pets. Currently, 14 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Windy Hills often include amenities such as Fireplace/Heating, Bedding/Linens, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.