Simpsonville Vacation Rentals
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50 rentals in Simpsonville.
Farm House - Near Bourbon Trail & Pet Friendly
Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Carriage House Cottage on horse farm.
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Southern Colonial Estate in Horse Country -Less than 30 miles to Churchill Downs
Rental Home
6 bedrooms
4 bathrooms
Sleeps 15
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Horse Farm Stay 4br Bourbon Trail ~ private pool
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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The following properties within 20 miles of Simpsonville match all your filters:
Historically Registered 1847 log Cabin
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Historic home freshly renovated on the Bourbon Trail
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
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Upscale Kentucky Bourbon Trail & Close to Louisville
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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Your Kentucky Home Away From Home
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful restored Victorian farmhouse
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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Unique Downtown Studio with an Industrial Vibe
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Bourbon Country Cabin with HOT TUB on Brashears Creek
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Downtown Main Street Suite w/ Hi-Speed Wifi
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Private Home Gallery | Louisville| New Listing | Hot Tub | Modern | Bourbon
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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New Modern Townhome, sleeps 6! Mod Farm 1217
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique Serenity - Entire Home On Private 3-Acres in Metro Area.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
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The Bluegrass Ranch - Secluded Luxury Cabin
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Upscale Kentucky Bourbon Trail & Close to Louisville
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bourbon Country Lodge • 5 Acre Resort Pool+Hot Tub
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
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Near Highways and a 20 Min Drive to Louisville's Main Attractions
Rental Home
6 bedrooms
3 bathrooms
Sleeps 18
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Le Coop Ultra Luxury 2 bed Urban Loft on Bourbon Trail. Downtown Shelbyville KY
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Upscale Kentucky Bourbon Trail & Close to Louisville
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SLEEPS 6! Loft w/1 Queen & 2 Doubles, Bar, 2 TVs
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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oasis 522!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Huge ROMANTIC apartment for short or long stays
Condo/Apartment in East Louisville
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Horses, Bourbon and More .... Shelbyville Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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New Modern Townhome, sleeps 6. Mod Farm 1219
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Snug little cottage on Chickapoo Farm
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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Heritage House 1900’s home part/close to the Bourbon Trail
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
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Bourbon Trail Bed, Bath & Private Guest Boutique on Elk Creek
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
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Enchanted Cabin at LedgeRock Springs
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
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Bourbon Trail Cottage on Chickapoo Farm
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Hygge Creek Cottage BB& Private Guest Boutique
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Charming 1900’s house close to downtown Shelbyville
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
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LIKE NEW! Sleeps 10+ Lakeside Farmhouse - 45 Acres
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bottled in Bond: Featured on HGTV, Heart of Bourbon Trail, Sleeps 10
Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Kentucky Derby House Rentals
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rent your Derby house! Updated, amenities, minutes from Valhalla!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Derby Retreat
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Talk DERBY to Me! 3 Min to Valhalla, 25 Min to Churchill Downs
Rental Home in East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Urban Loft Downtown Shelbyville - *5,000 Sq Ft., Sleeps 17
Condo/Apartment
5 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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Large house on 5 acres with pool
Rental Home
5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Executive East End Derby Home with Heated Pool
Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Available for Derby 2023!!
Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Derby done in style and luxury.
Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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⭐️NEW! - Large & Small Groups | Sleeps up to 16 |6br's | 6 baths - 3,000 sqft.
Condo/Apartment
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Derby / PGA House - 9700 Sq Ft - Perfect for 5 couples!
Rental Home
5 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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The Persimmon Ridge Lodge
Rental Home
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Brand New 2 Bedroom Townhouse
Rental Home in East Louisville
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Wooded Retreat PLUS Derby
Rental Home in East Louisville
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Simpsonville
- Yes, here are some popular vacation rentals in Simpsonville that have a pool:
- Horse Farm Stay 4br Bourbon Trail ~ private pool
- Farm House - Near Bourbon Trail & Pet Friendly
- Carriage House Cottage on horse farm.
- Yes, here are some popular vacation rentals in Simpsonville that have internet access:
- Farm House - Near Bourbon Trail & Pet Friendly
- Carriage House Cottage on horse farm.
- Southern Colonial Estate in Horse Country -Less than 30 miles to Churchill Downs
- Some of the most popular kid friendly rentals in Simpsonville are:
- Farm House - Near Bourbon Trail & Pet Friendly
- Carriage House Cottage on horse farm.
- Southern Colonial Estate in Horse Country -Less than 30 miles to Churchill Downs
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