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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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

Charming shotgun home, in the heart of Louisville!
Outdoor dining

Charming shotgun home, in the heart of Louisville!

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, in the heart of Louisville!
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

9.2 out of 10, Wonderful, (15)
"We had a great stay. Good beds and nice layout. Wonderful house and area. Everyone was friendly with great service. "
The price is SAR 521
SAR 1,006 total
includes taxes & fees
4 Apr - 5 Apr
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, (74)
"Very nice place. I would recommend it. "
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 790
SAR 2,154 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.
Terrace/patio

Spacious and Beautiful home near downtown Louisville, Kentucky.

10.0 out of 10, Exceptional, (2)
"Our family of four adults just needed a one night stay on our trip to Alabama. We were very pleased with this house. There was a small basket of welcoming snacks that we all sampled before we unpacked, Yummy. The rooms were very comforrable and nicely decorated, we all felt right at home. My daughter chose the bunk beds, she is an adult but was comfortable on the smaller bed. We were surprised and happy to see how well stocked the kitchen was. We didn't need a lot for one night but appreciated...
The price is SAR 446
SAR 1,039 total
includes taxes & fees
3 Apr - 4 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, (63)
"Very neat place. Very satisfying for all of us."
The price is SAR 2,247
SAR 4,467 total
includes taxes & fees
7 Apr - 8 Apr
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Fridge, microwave, oven, stovetop

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

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 2,363 total
includes taxes & fees
14 Apr - 15 Apr
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
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, (189)
"Everything was as expected and told. Deirdre is an awesome host. She is very responsive and makes everything come off without a flaw. She is also a very friendly person. The stay was more enjoyable because of all the little things done well. Our friends requested an extra day and they were allowed without any issue. That was excellent"
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 673
SAR 1,596 total
includes taxes & fees
5 Apr - 6 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 1,115 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, (19)
"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
Exterior

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

10.0 out of 10, Exceptional, (146)
"We (two moms traveling with two teens) came to Louisville for a national volleyball tournament at the Expo and couldn’t have picked a better place to stay! From the moment we booked, James was an incredible host—super communicative, helpful, and easy to work with.The house itself was spotless, beautifully decorated with a fun eclectic style, and had plenty of space for all of us to spread out comfortably. The beds were incredibly cozy, and honestly, this was the best-equipped home we’ve ever...
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, (19)
"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)
"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
Outdoor dining

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

2.5 star property
10.0 out of 10, Exceptional, (5)
"The house was perfect for our group. It was clean and the decor was beautiful. Judy s short ride to all of our Louisville destinations. The host was very responsive. We look forward to staying at this property again!"
The price is SAR 10,319
SAR 16,317 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
TV, offices

3 BR Downtown Sanctuary! Huge back yard

8.6 out of 10, Excellent, (27)
"House was very nice"
The price is SAR 356
SAR 839 total
includes taxes & fees
3 Apr - 4 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, (27)
"When arriving at the property it was very clean and well prepared! Kristin communicated with us anytime we needed. I would 100% recommend. Very cozy location! Thankful to have had such a pleasant experience! "
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, (224)
"Came into town for a concert at the Yum Center. The hotel isn’t close enough to walk but we did Lyfts there and back and it worked out really well. The room was very clean and the bed was comfy. The only draw back was the heat/air unit hummed, it didn’t bother me one bit, but my husband mentioned that it did keep him up once he was awake. If you want a place with a kitchen and clean and comfy, this is your place. "
The price is SAR 329
SAR 599 total
includes taxes & fees
6 Apr - 7 Apr
Hancock House
Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (91)
"Outstanding!"
The price is SAR 453
SAR 721 total
includes taxes & fees
20 Apr - 21 Apr
Stellar Suites
The Bellwether Hotel
Highland Station Penthouse Suite | Private kitchen | Microwave, coffee/tea maker, paper towels

The Bellwether Hotel

2.0 star property
8.0 out of 10, Very Good, (11)
"Beautifully redone historic building. Enjoyed design features and Christmas decor! Great walkable neighborhood. "
The price is SAR 544
SAR 631 total
includes taxes & fees
17 Apr - 18 Apr
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.