Search Vacation Homes in Simpsonville

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 635 Vacation Homes in Simpsonville with updated reviews, rates, and availability.

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

9.0 out of 10, Wonderful, (20)
"Wonderful set up for our ladies weekend. Tyler was easy to work with and very responsive. Jeffersonville is a hidden gem!"
The price is SAR 379
SAR 1,332 total
includes taxes & fees
26 Dec - 27 Dec
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Historic District Townhouse in City's BEST Location
Interior

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (183)
"This was a great stay and the property was so well-managed! Super easy to check in, everything was in great condition. Comfortable beds, and pretty much anything you need in the kitchen. The property was spotless. They provide white noise machines to mask outdoor noises, since it's on a commercial strip, but we didn't need them. Just note that you do need to climb stairs to get to the bedrooms. Deirdre was super-responsive to questions. Highly recommend."
Historic District Townhouse in City's BEST Location
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade
Interior detail

River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

9.8 out of 10, Exceptional, (48)
"Close to the Expo for the livestock show stay. House was clean. Beds were comfortably. "
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Original stained glass windows adorn your expansive living area!

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

10.0 out of 10, Exceptional, (137)
"Stayed for a few nights with family over Thanksgiving. Communication with James was outstanding. The house is exactly as pictured, which means it is interesting and beautiful, combining modern comforts with original beauty. Neighborhood could not have been better - quiet but with extremely easy walking access to a ton of stuff. Highly recommend!"
The price is SAR 702
SAR 1,474 total
includes taxes & fees
30 Dec - 31 Dec
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Open floor plan with lots of light.

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

10.0 out of 10, Exceptional, (33)
"The house was a great location for doing a lot of the distilleries. With my big group we had no problems with places to sleep and hang out. A+++"
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Newly Renovated Studio! Ideal location for walking to restaurants & shops
1,000 sq foot studio. Fully renovated with new furniture, appliances, etc

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

9.8 out of 10, Exceptional, (23)
"Place was very clean and cozy. Easy to get in and out and owner was very responsive. "
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail
Enjoy a meal on the deck or play games in the massive backyard. There's plenty of room to get a game of Cornhole going.

Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail

9.8 out of 10, Exceptional, (26)
"Property was clean and had amenities we needed. Great place to stay as a starting point to other points of interest. Needed to be careful where you went in some surrounding neighborhoods."
The price is SAR 285
SAR 1,022 total
includes taxes & fees
5 Jan - 6 January 2025
Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Shelbyville Vacation Rental | 3BR | 2BA | 1,700 Sq Ft | Steps Required to Access

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

9.8 out of 10, Exceptional, (11)
"There are a few issues with the listing and the property. Very happy overall with our stay. However, second bathroom door does not latch. No heat register in the second bathroom which makes it very cold. Master bedroom door does not latch. Grounds were not kept up very well. Extensions cords laying across the back sidewalk. Yard is NOT fenced in like the description indicates. We loved the location and the overall layout of the house, just needs some attention. "
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Derby Cigar & Bourbon Lounge Group Stays in charming Louisville
Exterior detail

Derby Cigar & Bourbon Lounge Group Stays in charming Louisville

The price is SAR 710
SAR 2,049 total
includes taxes & fees
26 Dec - 27 Dec
Derby Cigar & Bourbon Lounge Group Stays in charming Louisville
7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

10.0 out of 10, Exceptional, (15)
"Was in Louisville for a bachelor party (20 of us). The house was amazing! Plenty of space, very clean, great location. Would definitely recommend for larger groups."
7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home
Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi
Private kitchen

Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi

10.0 out of 10, Exceptional, (59)
"Very nice. Beautifully decorated "
The price is SAR 285
SAR 763 total
includes taxes & fees
5 Jan - 6 January 2025
Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi
5BR Very Spacious Home! Perfect for Family!
012

5BR Very Spacious Home! Perfect for Family!

8.8 out of 10, Excellent, (9)
"We had a great stay! Beautiful home in a safe and quiet neighborhood. Great communication with host. Comfortable accommodations for 10 adults. Easy access to Freedom Hall where our event was hosted."
The price is SAR 334
SAR 1,431 total
includes taxes & fees
24 Dec - 25 Dec
5BR Very Spacious Home! Perfect for Family!
Cozy, historic, pet-friendly home!
Living area

Cozy, historic, pet-friendly home!

9.8 out of 10, Exceptional, (14)
"The home is just as it appears in the photos....very charming and entertaining with seasonal decorations. The home was clean and comfortable. We enjoyed the gas firepit outside after touring the town. We will return during this season as the decorations for walking tours and historical site visits were amazing. Great location."
The price is SAR 920
SAR 1,461 total
includes taxes & fees
27 Dec - 28 Dec
Cozy, historic, pet-friendly home!
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Exterior

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (61)
"Really enjoyed the house, very spacious. Great host as well, would recommend staying here!"
The price is SAR 2,438
SAR 4,722 total
includes taxes & fees
6 Jan - 7 January 2025
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Spring blooms!

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

9.8 out of 10, Exceptional, (80)
"The host of this property is great. She communicates well and was easily accessible. The property is clean and in a great location if you are looking for things south of Louisville. Great layout for families with kids and in-laws. "
The price is SAR 563
SAR 1,664 total
includes taxes & fees
5 Jan - 6 January 2025
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
The Orange Door welcomes you to Louisville

The Orange Door ~ Prime Germantown 4BR/2BA Luxury

10.0 out of 10, Exceptional, (19)
"It was pretty solid no real complaints."
The price is SAR 597
SAR 1,490 total
includes taxes & fees
5 Jan - 6 January 2025
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
Updated 3 Bedroom Centrally Located Near Downtown
Living room

Updated 3 Bedroom Centrally Located Near Downtown

9.2 out of 10, Wonderful, (27)
"Exactly like pics, clean everything worked, nice extras like washer dryer"
The price is SAR 387
SAR 1,256 total
includes taxes & fees
24 Dec - 25 Dec
Updated 3 Bedroom Centrally Located Near Downtown
Ultra Modern in NuLu|Hot Tub|Fire Pit|King Bed
All the amenities you need to entertain the group

Ultra Modern in NuLu|Hot Tub|Fire Pit|King Bed

9.6 out of 10, Exceptional, (38)
"Great location for downtown and area. Very nice property. Neighborhood is a little sketchy but no issues. Would stay there again when coming to Louisville "
The price is SAR 376
SAR 1,487 total
includes taxes & fees
12 Jan - 13 January 2025
Ultra Modern in NuLu|Hot Tub|Fire Pit|King Bed
RIVERFRONT - Boat Slips - 10 Min to Dtown Lville
Terrace/patio

RIVERFRONT - Boat Slips - 10 Min to Dtown Lville

10.0 out of 10, Exceptional, (121)
"We (myself and my 12, 15, and 17 year old children) took a last minute fall break trip down south and chose this amazing home to stay in for a couple nights. WOW, did NOT disappoint!!!! The proximity to Louisville is awesome, but there are also so many great little restaurants right there in Jeffersonville. This home was probably the best part of the trip though. It ended up being a little too chilly for us to take advantage of all the cool outside activities (ping pong, volleyball, you...
RIVERFRONT - Boat Slips - 10 Min to Dtown Lville
THE BARRET HOUSE, 2 floor luxury home, LOCATION! Downtown, HIGHLANDS, NuLu, EXPO

THE BARRET HOUSE, 2 floor luxury home, LOCATION! Downtown, HIGHLANDS, NuLu, EXPO

10.0 out of 10, Exceptional, (68)
"Our family enjoyed the location and cleanliness of property. Thank you for hosting our clan!"
THE BARRET HOUSE, 2 floor luxury home, LOCATION! Downtown, HIGHLANDS, NuLu, EXPO
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.
Don't see what you're looking for?
See all available properties in Simpsonville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Simpsonville

Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (88)
"Outstanding!"
The price is SAR 441
SAR 708 total
includes taxes & fees
14 Jan - 15 January 2025
Stellar Suites
Hancock House
Exterior

Hancock House

3.0 star property
8.0 out of 10, Very Good, (197)
"I was impressed with the room. It smelled nice, it was clean, and I really liked the design. They programmed a set of codes for me and they were easy to follow. I also felt like the parking was safe. I would definitely stay there again. "
The price is SAR 319
SAR 589 total
includes taxes & fees
25 Dec - 26 Dec
Hancock House
The Bellwether Hotel
Front of property

The Bellwether Hotel

2.0 star property
7.4 out of 10, Good, (8)
"Love the convenience of checking in, location, and rooms and property were gorgeous! "
The price is SAR 395
SAR 458 total
includes taxes & fees
5 Jan - 6 January 2025
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.