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Compare 821 Vacation Homes in Simpsonville with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (23)
"We had a great time during our stay in Louisville. The house was clean and just as the listing described. I’ll definitely stay here again next time I’m in town."
Charming shotgun home, 3 miles from Churchill Downs & the 151st Kentucky Derby!

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 AED 621
AED 1,111 total
includes taxes & fees
28 Apr - 29 Apr
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Enchanting, energizing, and enjoyable!

10.0 out of 10, Exceptional, (75)
"Excellent property, well located to enjoy Louisville’s best attractions."
Enchanting, energizing, and enjoyable!

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 AED 774
AED 2,109 total
includes taxes & fees
14 Apr - 15 Apr
Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky

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 437
AED 1,017 total
includes taxes & fees
13 Apr - 14 Apr
Spacious and Beautiful home near downtown Louisville, Kentucky.

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

9.8 out of 10, Exceptional, (64)
"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 AED 2,016
AED 4,131 total
includes taxes & fees
14 Apr - 15 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

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 AED 1,098
AED 2,314 total
includes taxes & fees
14 Apr - 15 Apr
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

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✪

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 AED 317
AED 1,121 total
includes taxes & fees
13 Apr - 14 Apr
✪Heated Pool, Firepit, Bikes, Grill, Pets✪

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!

The price is AED 735
AED 1,096 total
includes taxes & fees
28 Apr - 29 Apr
Highlands Home: Bourbon, Derby, Bar, Karaoke & Fun!

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

10.0 out of 10, Exceptional, (20)
"My husband and I were in town to visit our daughter (goes to U of L) for the weekend. Very comfortable house with everything we needed - will definitely keep it on the list of places to re-visit!"
Cozy Cottage-Bourbon Trail, Expo, YUM, Derby!

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

10.0 out of 10, Exceptional, (148)
"We loved the decor, coziness and location of this quaint property! It had everything we needed for a comfortable, fun stay in Louisville! We will definitely stay here again! "
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

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

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

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

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

2.5 star property
10.0 out of 10, Exceptional, (6)
"This house was perfect for our company. We were able to spread out and have our own rooms. The host was amazing! We unfortunately had scary weather while we were there and Kapil went above and beyond to make sure we were safe. Would definitely stay here again!"
The price is AED 9,384
AED 15,032 total
includes taxes & fees
24 Apr - 25 Apr
Sleeps24~6000SF~Louisville~YardOasis~Dome~HotTub~Firepit~Pet~Lux Amenities~Views

3 BR Downtown Sanctuary! Huge back yard

8.8 out of 10, Excellent, (28)
"House was very nice"
The price is AED 349
AED 826 total
includes taxes & fees
13 Apr - 14 Apr
3 BR Downtown Sanctuary! Huge back yard

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

9.8 out of 10, Exceptional, (28)
"Beautiful spot! The unit is cozy and clean. Good amenities, a well stocked kitchen, and spacious bathroom. The location is was makes this unit the best though. Right on Frankfort Ave. but not too noisy at night. Great stay!"
Newly Renovated Studio! Ideal location for walking to restaurants & shops

✨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

3.0 star property
8.0 out of 10, Very Good, (229)
"Great stay!"
The price is AED 322
AED 587 total
includes taxes & fees
13 Apr - 14 Apr
Hancock House

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (92)
"Outstanding!"
The price is AED 492
AED 763 total
includes taxes & fees
14 Apr - 15 Apr
Stellar Suites

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.