Search Vacation Homes in Simpsonville

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Vacation Homes in Simpsonville

Outdoor dining
Angels Envy 29 - A relaxing place by the lake!

Angels Envy 29 - A relaxing place by the lake!

Taylorsville
9.4 out of 10, Exceptional, (20)
"Great place good accommodation "
United States
Ryan D.
$273 nightly
The price is $300
Dec 4 - Dec 5
Total with taxes and fees
Angels Envy 29 - A relaxing place by the lake!
Outdoor spa tub
Kentucky Sunrise 18- Greet the Sun As it Rises

Kentucky Sunrise 18- Greet the Sun As it Rises

Taylorsville
9.8 out of 10, Exceptional, (51)
"Great place - everything and more!Suzanne was super helpful!"
United States
leslie Z.
$285 nightly
The price is $314
Dec 4 - Dec 5
Total with taxes and fees
Kentucky Sunrise 18- Greet the Sun As it Rises
Fridge, microwave, oven, stovetop
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Pendleton
9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
$212 nightly
The price is $234
Dec 13 - Dec 14
Total with taxes and fees
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Outdoor spa tub
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Frankfort
10.0 out of 10, Exceptional, (18)
"Awesome place, it was clean and spacious! "
United States
Ben M.
$402 nightly
The price is $456
Dec 7 - Dec 8
Total with taxes and fees
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Dining
Creative & Bright Cozy Unit in Lou's Art District!

Creative & Bright Cozy Unit in Lou's Art District!

Merriwether
10.0 out of 10, Exceptional, (3)
"Place was clean and fit our needs well. "
United States
sean g.
$210 nightly
The price is $224
Dec 4 - Dec 5
Total with taxes and fees
Creative & Bright Cozy Unit in Lou's Art District!
Outdoor spa tub
Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)

Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)

Taylorsville
9.6 out of 10, Exceptional, (53)
"We had a girls weekend and everything was perfect. Would definitely stay here again."
United States
Susan N.
$255 nightly
The price is $281
Dec 4 - Dec 5
Total with taxes and fees
Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)
Exterior
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

St. Matthews
9.0 out of 10, Wonderful, (6)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
$228 nightly
The price is $264
Dec 9 - Dec 10
Total with taxes and fees
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
Outdoor spa tub
Modern Farmhouse Near Distilleries! Hot tub, GameRoom, Firepit, Luxury, 5-Acres!

Modern Farmhouse Near Distilleries! Hot tub, GameRoom, Firepit, Luxury, 5-Acres!

Bagdad
9.4 out of 10, Exceptional, (10)
"I had my bachelor party here and it was the perfect place to get away!"
United States
Kyser M.
$473 nightly
The price is $526
Dec 7 - Dec 8
Total with taxes and fees
Modern Farmhouse Near Distilleries! Hot tub, GameRoom, Firepit, Luxury, 5-Acres!
Exterior detail
Close to Everything in Louisville!!!

Close to Everything in Louisville!!!

Camp Taylor
9.4 out of 10, Exceptional, (37)
"Matches the description and photos "
United States
Angela C.
$220 nightly
The price is $255
Dec 8 - Dec 9
Total with taxes and fees
Close to Everything in Louisville!!!
Fridge, microwave, oven, stovetop
Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Bon Air
10.0 out of 10, Exceptional, (5)
"This was a very pleasant and comfortable stay at this home! I thoroughly enjoyed the decor, and everything was clean and well-maintained. Overall, it was a great stay."
United States
Brionna W.
$267 nightly
The price is $310
Dec 16 - Dec 17
Total with taxes and fees
Lumos Stays: 65" 4K TV, memory foam, kid-friendly
Fridge, microwave, oven, stovetop
Close to Expo Ctr, UofL, Walk to bars, shops!

Close to Expo Ctr, UofL, Walk to bars, shops!

Germantown
10.0 out of 10, Exceptional, (70)
"The place was very clean and organized. Furniture, floors, and appliances are all of good quality. I enjoyed my stay and would definitely book again "
United States
Victor H.
$166 nightly
The price is $192
Dec 4 - Dec 5
Total with taxes and fees
Close to Expo Ctr, UofL, Walk to bars, shops!
Exterior
The Barefoot Cottage 53. Pet friendly with fee, NEW HOT TUB

The Barefoot Cottage 53. Pet friendly with fee, NEW HOT TUB

Taylorsville
9.8 out of 10, Exceptional, (37)
"This place was amazing. Right by the water too."
United States
Tiffany W.
$361 nightly
The price is $397
Dec 4 - Dec 5
Total with taxes and fees
The Barefoot Cottage 53. Pet friendly with fee, NEW HOT TUB
Fridge, microwave, oven, stovetop
The Burnt Barrel | New HotTub & Grill | Backyard!

The Burnt Barrel | New HotTub & Grill | Backyard!

2.0 star property
Germantown
10.0 out of 10, Exceptional, (1)
"Excellent walking to different little shops. Super decorated inside and out. Loved the hot tub. Would stay again! "
United States
kevin m.
$212 nightly
The price is $228
Dec 9 - Dec 10
Total with taxes and fees
The Burnt Barrel | New HotTub & Grill | Backyard!
2 bedrooms, WiFi, bed sheets
Stylish House Walking Distance from the Fun of the Highlands!

Stylish House Walking Distance from the Fun of the Highlands!

Phoenix Hill
9.6 out of 10, Exceptional, (24)
"We enjoyed our stay. The place was just as advertised. The host was so helpful and easy to reach. "
United States
Trena D.
$175 nightly
The price is $203
Dec 8 - Dec 9
Total with taxes and fees
Stylish House Walking Distance from the Fun of the Highlands!
Private kitchen
Putt Putt House by Louisville Walking Bridge

Putt Putt House by Louisville Walking Bridge

2.0 star property
Jeffersonville
10.0 out of 10, Exceptional, (9)
"Beautiful property in lovely area "
United States
A. Dawn
$260 nightly
The price is $294
Dec 7 - Dec 8
Total with taxes and fees
Putt Putt House by Louisville Walking Bridge
Fridge, microwave, oven, stovetop
Stylish Jeffersonville Home - Mins from Louisville

Stylish Jeffersonville Home - Mins from Louisville

Jeffersonville
9.0 out of 10, Wonderful, (20)
"This was a great place for us to stay for an event at the expedition center. Close to the highway for quick access to the city. "
United States
Chad L.
$281 nightly
The price is $317
Dec 4 - Dec 5
Total with taxes and fees
Stylish Jeffersonville Home - Mins from Louisville
Fridge, microwave, oven, stovetop
Private Home Close to Zoo, U of L, Churchill Downs

Private Home Close to Zoo, U of L, Churchill Downs

Poplar Level
9.6 out of 10, Exceptional, (18)
"I love this property! Great neighborhood near the park and zoo, comfortable beds, and a nice living room to hang out in. Very charming older home"
United States
Rosemary P.
$266 nightly
The price is $311
Dec 4 - Dec 5
Total with taxes and fees
Private Home Close to Zoo, U of L, Churchill Downs
Exterior
St. Matthews Retreat | Relaxing Home w/ Backyard!

St. Matthews Retreat | Relaxing Home w/ Backyard!

2.0 star property
Rockcreek Lexington Road
10.0 out of 10, Exceptional, (3)
"Fantastic service. The home was beautiful and if in town again we would definitely stay there again. Nice area great access to amenities. "
United States
T J.
$411 nightly
The price is $450
Dec 4 - Dec 5
Total with taxes and fees
St. Matthews Retreat | Relaxing Home w/ Backyard!
Terrace/patio
Fam & Business Stay | Cozy Home in Prime Location!

Fam & Business Stay | Cozy Home in Prime Location!

2.0 star property
Smoketown Jackson
10.0 out of 10, Exceptional, (2)
"Great location for our stay while attending the state fair. Fit all of us perfectly. Beautifully remodeled 20th century home. Host was amazing. "
United States
Le Ann G.
$215 nightly
The price is $229
Dec 8 - Dec 9
Total with taxes and fees
Fam & Business Stay | Cozy Home in Prime Location!
Exterior
Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Taylorsville
9.8 out of 10, Exceptional, (24)
"Very nice house, new hot tub in the resort it was located in was very nice"
United States
Mike O.
$366 nightly
The price is $403
Dec 4 - Dec 5
Total with taxes and fees
Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB
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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Top Simpsonville Hotel Reviews

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

10/10 Excellent
"Clean rooms and front desk staff very pleasant."
Kim 1-night trip
Posted 2 days ago
Derby City Gaming & Hotel - A Churchill Downs Property

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Simpsonville Vacation Homes information

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