Simpsonville Holiday Rentals
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5 mi
48 rentals in Simpsonville.
Farm House - Near Bourbon Trail & Pet Friendly
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Carriage House Cottage on horse farm.
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Charming 2-bedroom house in Simpsonville with AC
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bourbon trail home w/ screened-in porch & firepit near Louisville
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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4Br Home on Sabre Hill Horse Farm 25 acres ~ Bourbon Trail
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sleeps 24, 6BR, 4BA, Hot Tub
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The following properties within 20 miles of Simpsonville match all your filters:
Historically Registered 1847 Cabin
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Historic home freshly renovated on the Bourbon Trail
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Upscale Kentucky Bourbon Trail & Close to Louisville
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Unique Downtown Studio with an Industrial Vibe
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Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
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New Modern Townhome, sleeps 6! Mod Farm 1217
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Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon
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Upscale Kentucky Bourbon Trail & Close to Louisville
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Bourbon Country Lodge • 5 Acre Resort Pool+Hot Tub
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Near Highways and a 20 Min Drive to Louisville's Main Attractions
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LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others
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Upscale Kentucky Bourbon Trail & Close to Louisville
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oasis 522!
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Huge ROMANTIC apartment for short or long stays
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Heritage House 1900’s home part/close to the Bourbon Trail
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Peace and Quiet Close to Louisville - 80+ Acres
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Charming 1900’s house close to downtown Shelbyville
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Rent your Derby house! Updated, amenities, minutes from Valhalla!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Large house on 5 acres with pool
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Executive East End Derby Home with Heated Pool
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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6BR~~Close to PGA 2024! On Persimmon Ridge Golf Course!
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Derby done in style and luxury.
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Saddlebred Suites 6 bed, 6 ba
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Derby / PGA House - 9700 Sq Ft - Perfect for 5 couples!
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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The Persimmon Ridge Lodge - Indoor Golf & Pickleball!
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EV Charger/Bourbon Trail/Hot Tub/Fire Pit/Game Room
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3 MINUTES TO VALHALLA- 7 Bedroom Luxury Estate
Holiday Rental House
7 bedrooms
11 bathrooms
Sleeps 16
Match: Sleeps
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Private 6-acre haven in serene east Louisville near Valhalla.
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Cozy farmhouse on Kentucky horse farm
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 4-bedroom house with WiFi and AC in fabulous Louisville
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New Year Special| Convenient Location | Cozy
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Louisville Country Manor - Pool & Pickleball!
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Charming Home in Historic Downtown Shelbyville
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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5,000 sq ft 5-bedroom golf course home with walkout - 2 miles from Valhalla!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
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Modern barn home on a Kentucky horse farm
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bourbon Trail | Hot Tub | Speakeasy | Game Rm!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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10 minute walk to Valhalla
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers
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Shelbyville Home - On to the Bourbon Trail!
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Historic Home Farm Stay in the Heart of Bourbon Country
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Showing results 1-48 of 48
Frequently Asked Questions about Simpsonville
- Yes, here are some popular holiday rentals in Simpsonville that have a pool:
- Farm House - Near Bourbon Trail & Pet Friendly
- Carriage House Cottage on horse farm.
- Charming 2-bedroom house in Simpsonville with AC
- Yes, here are some popular holiday rentals in Simpsonville that have internet access:
- Farm House - Near Bourbon Trail & Pet Friendly
- Carriage House Cottage on horse farm.
- Charming 2-bedroom house in Simpsonville with AC
- The best pet friendly rentals in Simpsonville are:
- Farm House - Near Bourbon Trail & Pet Friendly
- Sleeps 24, 6BR, 4BA, Hot Tub
- Carriage House Cottage on horse farm.
- Some of the most popular kid friendly rentals in Simpsonville are:
- Farm House - Near Bourbon Trail & Pet Friendly
- Carriage House Cottage on horse farm.
- Charming 2-bedroom house in Simpsonville with AC
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