Simpsonville Holiday Rentals

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Holiday Rentals in Simpsonville

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

9.6 out of 10, Exceptional, (25)
"The house felt like we were staying at a family members. With its old charm and well appointed appliances, we couldn’t have asked for more. Perfect location in such a charming town. "
The price is NZ$404
includes taxes & fees
16 July - 17 July
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Bourbon Trail | Hot Tub | Speakeasy | Game Rm

2.0 star property
10.0 out of 10, Exceptional, (8)
"Such a beautiful house it was just as described very clean and in a great location for the bourbon trail I would stay again hands down."
The price is NZ$961
includes taxes & fees
12 Aug - 13 Aug
Bourbon Trail | Hot Tub | Speakeasy | Game Rm

The Sweet Retreat Wheelchair Accessible Historic Home

2.0 star property
10.0 out of 10, Exceptional, (4)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
The price is NZ$817
includes taxes & fees
3 Aug - 4 Aug
The Sweet Retreat Wheelchair Accessible Historic Home

Reduced rates for remaining July dates - Completed renovated 1,900 sq ft home!

10.0 out of 10, Exceptional, (8)
"Very nice house, spacious, clean and very comfortable. Perfect for our stay to attend a conference in the area. Highly recommend!!"
Reduced rates for remaining July dates - Completed renovated 1,900 sq ft home!

NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

10.0 out of 10, Exceptional, (1)
"Our family of 8 adults and two young grandchildren absolutely loved this property! The home is beautifully decorated, and the kitchen is both stunning and fully equipped with everything you could possibly need, and more.The barn was a fantastic bonus: a fun and safe place for our grandsons to burn off energy before bedtime, and a perfect spot for the adults to unwind and enjoy games together.From the moment we booked until checkout, Melissa was incredibly responsive and helpful. We couldn’t have...
The price is NZ$1,181
includes taxes & fees
12 Aug - 13 Aug
NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

Near Highways and a 20 Min Drive to Louisville's Main Attractions

10.0 out of 10, Exceptional, (41)
"Great for a big group. Host was great!"
The price is NZ$714
includes taxes & fees
20 July - 21 July
Near Highways and a 20 Min Drive to Louisville's Main Attractions

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

9.8 out of 10, Exceptional, (17)
"Great place good time "
The price is NZ$1,079
includes taxes & fees
16 July - 17 July
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Charming house in one of Louisville's most coveted neighborhoods

10.0 out of 10, Exceptional, (71)
"Cozy, quiet, scenic property run by an extremely responsive host."
The price is NZ$489
includes taxes & fees
16 July - 17 July
Charming house in one of Louisville's most coveted neighborhoods

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

9.8 out of 10, Exceptional, (68)
"This place was a perfect stay for my bachelor party! There was a ton of room, the host was very responsive with any questions and it had everything we needed. Highly recommend! "
The price is NZ$2,048
includes taxes & fees
15 July - 16 July
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Huge and Contemporary Norton Commons House!

9.6 out of 10, Exceptional, (40)
"Great neighborhood in a highly sought after city! The home is beautiful and is in a short driving distance of shops, restaurants, grocery stores and the interstate. Please pay attention to the pictures as the houses are very close together but we never experienced any issues. Also, there is a small fenced in area but no grass so if you are traveling with pets please plan accordingly. However many spots in the neighborhood to walk dogs including a nice sized dog park. Excellent time in KY"
The price is NZ$1,020
includes taxes & fees
21 July - 22 July
Huge and Contemporary Norton Commons House!

Brand new home less than 30 mins away from Louisville's favorite destinations!

9.4 out of 10, Exceptional, (6)
"We really enjoyed our stay. "
The price is NZ$908
includes taxes & fees
26 July - 27 July
Brand new home less than 30 mins away from Louisville's favorite destinations!

Modern Spacious Home with Outdoor Retreat and Hot Tub

9.8 out of 10, Exceptional, (12)
"This house is super fun. Really cool decorating. Back patio and hot tub are top notch. Niki is a fantastic host and took good care of us! Highly recommend."
The price is NZ$1,156
includes taxes & fees
27 July - 28 July
Modern Spacious Home with Outdoor Retreat and Hot Tub

4 rooms for rent

2.0 out of 10, (1)
"We ended up not staying due to not being able to get a hold of the host. Also called vrbo and they couldnt contact the host"
The price is NZ$232
includes taxes & fees
14 July - 15 July
4 rooms for rent

Hidden Gem: Stylish Comfort, Prime Location

9.4 out of 10, Exceptional, (9)
"This house was perfect! A well-appointed kitchen, comfortable beds, and convenient location all added up to a great stay! We appreciated the fire pit and four parking spaces, too. "
The price is NZ$716
includes taxes & fees
29 July - 30 July
Hidden Gem: Stylish Comfort, Prime Location

Luxury Waterfront Retreat, Louisville

9.8 out of 10, Exceptional, (8)
"This is an amazing rental property and friendly accommodating property managers! Great amenities, great location! We were in town for the Derby City National bmx race and this was the perfect property!"
The price is NZ$1,047
includes taxes & fees
14 July - 15 July
Luxury Waterfront Retreat, Louisville

The Derby House - Relaxing retreat before and after the excitement of the Derby!

9.8 out of 10, Exceptional, (12)
"Great place!"
The price is NZ$620
includes taxes & fees
12 Aug - 13 Aug
The Derby House - Relaxing retreat before and after the excitement of the Derby!

⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

9.6 out of 10, Exceptional, (46)
"Great hosts, good location for our family member, everything very nice!"
The price is NZ$786
includes taxes & fees
5 Aug - 6 Aug
⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

Spectacular waterfront house!

9.6 out of 10, Exceptional, (76)
"We had a great time and loved the view of the river! "
The price is NZ$879
includes taxes & fees
21 July - 22 July
Spectacular waterfront house!

The Jungalow: 65" 4K TV, memory foam, kid-friendly

9.8 out of 10, Exceptional, (14)
"Everything was as described and Ashley was a pleasure to deal with leading up to our trip and during our stay there! House was very clean and backyard was great to use during our stay here. Would highly recommend this place while visiting Louisville!"
The price is NZ$660
includes taxes & fees
27 July - 28 July
The Jungalow: 65" 4K TV, memory foam, kid-friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find a holiday rental in Simpsonville?

Yes, there are holiday rentals close to the most popular sights in Simpsonville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Simpsonville has to offer?

Newly renovated 4BR CozySuites: This holiday home rental outside of Simpsonville offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Simpsonville?

Choose from 8 Expedia holiday rentals in Simpsonville for a memorable holiday.

What’s there to see and do in Simpsonville?

While exploring the area, visit family-friendly sights like IceLand Sports Complex, or get outside and enjoy nature at Beckley Creek Park. The Outlet Shoppes of the Bluegrass and Whitney M. Young, Jr. Birthplace are other places to visit while you're in town.

What’s a holiday rental in Simpsonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpsonville. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.