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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 811 Vacation Homes in Simpsonville with updated reviews, rates, and availability.

Charming shotgun home, 3 miles from Churchill Downs & the 151st Kentucky Derby!
Outdoor dining

Charming shotgun home, 3 miles from Churchill Downs & the 151st Kentucky Derby!

9.6 out of 10, Exceptional, (24)
"House was clean and very nice. Description online was accurate and we enjoyed our stay very much!"
Charming shotgun home, 3 miles from Churchill Downs & the 151st Kentucky Derby!
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
3 bedrooms, travel crib, free WiFi, bed sheets

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

9.4 out of 10, Exceptional, (16)
"Great home!! Accurate listing!! Cutr"
The price is SAR 634
SAR 1,165 total
includes taxes & fees
18 May - 19 May
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Enchanting, energizing, and enjoyable!
Fridge, microwave, oven, stovetop

Enchanting, energizing, and enjoyable!

10.0 out of 10, Exceptional, (76)
"This home was everything we needed and more for our trip to Louisville. We stayed here for a volleyball tournament for my daughter. It was an easy, 25 minute drive from the expo convention center & there was plenty of room & activity’s for my other children to do when we weren’t at the convention center. We were able to accommodate her team & their parents for a team dinner & there was space for everyone to comfortably socialize! There is also a HUGE backyard for the kids to run around & stay...
Enchanting, energizing, and enjoyable!
Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky
Interior

Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky

10.0 out of 10, Exceptional, (1)
"Had a great stay at this property. Check-in was super easy, the house was beautiful and clean, host responded quick and helped with anything I needed. 10/10 would stay again."
The price is SAR 806
SAR 2,190 total
includes taxes & fees
21 Apr - 22 Apr
Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky
Spacious and Beautiful home near downtown Louisville, Kentucky.
Terrace/patio

Spacious and Beautiful home near downtown Louisville, Kentucky.

10.0 out of 10, Exceptional, (3)
"Easy access, clean, everything was great. "
The price is SAR 447
SAR 1,039 total
includes taxes & fees
19 Apr - 20 Apr
Spacious and Beautiful home near downtown Louisville, Kentucky.
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Interior

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

9.8 out of 10, Exceptional, (65)
"We needed a property with both indoor and outdoor space to hold our group of 13. This place was perfect! They were responsive to my revisit questions, the checkin and out process was easy and the home was amazing! We hope to book it again next year."
The price is SAR 2,060
SAR 4,220 total
includes taxes & fees
21 Apr - 22 Apr
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65
Fridge, microwave, oven, stovetop

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

10.0 out of 10, Exceptional, (88)
"Everything from top to bottom was fantastic about this property. The location was perfectly located to be able to go into Louisville or Bardstown. "
The price is SAR 1,122
SAR 2,381 total
includes taxes & fees
23 Apr - 24 Apr
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65
Historic District Townhouse in City's BEST Location
Fridge, microwave, oven, stovetop

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (190)
"Location was good; there was street noise but not bad. White noise units was not used, but it is a nice touch. Definitely need to be able to do stairs; the second bedroom has a alot of steps to get to. It was super clean and comfortable. Nice chairs/sofas in bedrooms, but a plus would be a lamp next to them so that you can enjoy setting and relaxing and READ "
Historic District Townhouse in City's BEST Location
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Fridge, microwave, oven, stovetop

✪Heated Pool, Firepit, Bikes, Grill, Pets✪

8.4 out of 10, Very Good, (10)
"House just as described! The pool was the selling point for us! Even in the beginning of March it was as warm as a hot tub! We had 2 families in town for a volleyball tournament and after a long day of volleyball it was perfect to just relax and unwind. We sat outside by the fire pit and made s’mores ( provided by host!). House is an older home with hardwood floors that tend to squeak a bit, but such great character! I am very picky about cleanliness and this house did not disappoint! We did...
The price is SAR 324
SAR 1,145 total
includes taxes & fees
22 Apr - 23 Apr
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Brand New Downtown Luxury Home
Outdoor dining

Brand New Downtown Luxury Home

10.0 out of 10, Exceptional, (9)
"This house was the perfect home base for our large group trip to Louisville! The location was very convenient - we were a few miles away from all the action on Whiskey Row, with tons of bars and restaurants right down the street. Despite being in the heart of downtown, the house itself was surprisingly spacious and comfortable. Plenty of room for everyone to spread out and relax, and the common areas were great for hanging out and playing games. We would definitely recommend this VRBO to...
Brand New Downtown Luxury Home
Highlands Home: Bourbon, Derby, Bar, Karaoke & Fun!
Living area

Highlands Home: Bourbon, Derby, Bar, Karaoke & Fun!

The price is SAR 750
SAR 1,119 total
includes taxes & fees
28 Apr - 29 Apr
Highlands Home: Bourbon, Derby, Bar, Karaoke & Fun!
Cozy Cottage-Bourbon Trail, Expo, YUM, Derby!
Outdoor dining

Cozy Cottage-Bourbon Trail, Expo, YUM, Derby!

10.0 out of 10, Exceptional, (22)
"The little house was cozy and was great for my family for our little stay. "
Cozy Cottage-Bourbon Trail, Expo, YUM, Derby!
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Exterior

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

10.0 out of 10, Exceptional, (149)
"Our host was wonderful! He was quick to respond to my messages - always helpful and polite. The house was comfortable with generously stocked kitchen and bathrooms. Good quality of towels and bedding were a plus! It's a cute home and comfortable. We enjoyed our stay and highly recommend the house and our host, James!"
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Stay on Broadway - Sleeps 10, Hot Tub, Walkable!
Exterior

Stay on Broadway - Sleeps 10, Hot Tub, Walkable!

9.4 out of 10, Exceptional, (3)
"Visit to celebrate my wife’s commencement, we all enjoyed our stay very much"
Stay on Broadway - Sleeps 10, Hot Tub, Walkable!
Family/Pet-Friendly Riverside Home w/Amazing Views
Terrace/patio

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (20)
"Nestled on the Ohio River in a quiet neighborhood close to Louisville (about 20 minutes). Pet friendly. Clean. Nice kitchen with appliances like a Keurig coffee machine, regular coffee pot, air fryer, and blender. Beds were not the most comfortable and neither was the furniture. Great shower! The yard needs attention. Looks like it went through a storm!"
Family/Pet-Friendly Riverside Home w/Amazing Views
Walk to Dinner, Pubs, Fun- Huge Historic District Home with Poker Room, Fire Pit
Outdoor dining

Walk to Dinner, Pubs, Fun- Huge Historic District Home with Poker Room, Fire Pit

10.0 out of 10, Exceptional, (133)
"Came down with my family and four other couples to do a bourbon trail trip for my fiancé’s 40th birthday. House was big and beautiful! Walking distance to plenty of nightlife. Wonderfully furnished and comfortable beds. Plenty of bathrooms for a packed house. Was perfect for this trip. Had great communication with the owners and our stay couldn’t have gone any better. Would highly recommend this rental and would definitely book again."
Walk to Dinner, Pubs, Fun- Huge Historic District Home with Poker Room, Fire Pit
6000SF*Sleeps24*Louisville*YardOasis*HotTub*Dome*Pet*Firepit*Lux Amenities*Views
Outdoor dining

6000SF*Sleeps24*Louisville*YardOasis*HotTub*Dome*Pet*Firepit*Lux Amenities*Views

2.5 star property
10.0 out of 10, Exceptional, (7)
"From the time of Booking Kapil was great at communicating. He was very professional and polite through out our stay, checking in and allowing us to reach out at our convenance. The property was as advertised. A quite location on the river with local bars and restaurants within walking distance. Our group enjoyed the backyard in the evenings playing corn hole and sitting around the fire. The place was very clean inside and out and all things where in working order. I would highly recommend for...
The price is SAR 9,978
SAR 15,598 total
includes taxes & fees
24 Apr - 25 Apr
6000SF*Sleeps24*Louisville*YardOasis*HotTub*Dome*Pet*Firepit*Lux Amenities*Views
3 BR Downtown Sanctuary! Huge back yard
TV, offices

3 BR Downtown Sanctuary! Huge back yard

8.8 out of 10, Excellent, (28)
"House was very nice"
The price is SAR 356
SAR 848 total
includes taxes & fees
20 Apr - 21 Apr
3 BR Downtown Sanctuary! Huge back yard
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Fridge, microwave, oven, stovetop

Newly Renovated Studio! Ideal location for walking to restaurants & shops

9.8 out of 10, Exceptional, (29)
"My teenage daughter and I stayed here for a volleyball tournament that was held at KICC. The location was perfect. Very short drive to the courts and many restaurants and stores were walkable from the house. Close to the airport too. This was perfect for our needs. "
Newly Renovated Studio! Ideal location for walking to restaurants & shops
✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16
Exterior

✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16

10.0 out of 10, Exceptional, (22)
"This place is in a great location. Secluded by near everything you need. The entire property was well maintained and the hosts were easy to work with and very prompt in response. There was an HVAC issue that changed the comfort aspect of our stay but overall the stay was great. "
✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16
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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Other property types in Simpsonville

Hancock House
Executive Room | View from room

Hancock House

3.0 star property
8.0 out of 10, Very Good, (231)
"Great stay!"
The price is SAR 371
SAR 649 total
includes taxes & fees
21 Apr - 22 Apr
Hancock House
Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (92)
"Outstanding!"
The price is SAR 486
SAR 760 total
includes taxes & fees
19 May - 20 May
Stellar Suites
Newly renovated 4BR CozySuites
House | Private kitchen | Fridge, microwave, oven, stovetop

Newly renovated 4BR CozySuites

4.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent "
Newly renovated 4BR CozySuites
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.