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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 821 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, (25)
"Perfect size and location. Would stay again."
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, (18)
"The home was well worth the price. The amenities were good and the home was welcoming. "
The price is AED 621
AED 1,140 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, (77)
"We stayed here for a group trip to the Bourbon Trail. Great property and neighborhood! "
Enchanting, energizing, and enjoyable!
Kentucky Derby 5 Bed Group 12+ Vacation Stay in Louisville Kentucky
Interior

Kentucky Derby 5 Bed Group 12+ Vacation Stay 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 AED 1,186
AED 2,668 total
includes taxes & fees
12 May - 13 May
Kentucky Derby 5 Bed Group 12+ Vacation Stay 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 AED 547
AED 1,154 total
includes taxes & fees
11 May - 12 May
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)
"Really enjoyed the house, very spacious. Great host as well, would recommend staying here!"
The price is AED 2,567
AED 4,860 total
includes taxes & fees
12 May - 13 May
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, (89)
"Nice, comfy home. The property was clean and convenient. Tammy was easy to contact and very helpful. Definitely would book again."
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, (192)
"Huge well appointed townhouse, nicely decorated and some of the most comfortable beds we have ever slept in!Restaurants, bars, art and coffee right out your front door. Rent this place. "
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, (11)
"The house was the perfect size and setup for my family. All bedrooms are upstairs so there privacy from downstairs noise. The house was very cozy, heat worked extremely well in the winter. We did not use the pool. Just a note, it’s small but big enough for a small group of people or family with young kids. Great price for the size of home in the area. "
The price is AED 1,033
AED 2,042 total
includes taxes & fees
10 May - 11 May
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Brand New Downtown Luxury Home
Outdoor dining

Brand New Downtown Luxury Home

9.8 out of 10, Exceptional, (10)
"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!

2.0 out of 10, (1)
"Horrible"
The price is AED 1,102
AED 1,607 total
includes taxes & fees
18 May - 19 May
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, (23)
"We stayed at the property while in Louisville for an event at the YUM Center and found that everything we needed was just a short drive away. We had a great stay and would definitely stay again if we are in the area. "
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, (152)
"Great time visiting family!"
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)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
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)
"Great house"
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)
"We had a great time- the property was perfect for our group of 14. Would stay here again!"
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, (29)
"Nice place, Great showers, extra tv, great kitchen great room for the family to hang together"
The price is AED 408
AED 901 total
includes taxes & fees
11 May - 12 May
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, (30)
"Great location and accommodations!"
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)
"Lovely home and helpful hosts. "
✨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, (232)
"Great stay!"
The price is AED 364
AED 764 total
includes taxes & fees
13 May - 14 May
Hancock House
Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (93)
"Great location! Excellent dining options nearby!"
The price is AED 393
AED 649 total
includes taxes & fees
26 May - 27 May
Stellar Suites
The Bellwether Hotel
Highland Station Penthouse Suite | Private kitchen | Microwave, coffee/tea maker, paper towels

The Bellwether Hotel

2.0 star property
8.4 out of 10, Very Good, (13)
"The boutique Bellwether Hotel is so beautiful and a step back in time. The art deco design, the second floor lounge, and the rooms all beautifully decorated and comfortable. Walk to restaurants, grocery, bars and antique shops. "
The price is AED 505
AED 586 total
includes taxes & fees
11 May - 12 May
The Bellwether Hotel
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.