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Vacation rentals in Simpsonville

Vacation rentals in Simpsonville

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Simpsonville

Guests agree: these stays are highly rated for location, cleanliness, and more.

Room w bath in quiet neighborhood
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
Room w bath in quiet neighborhood

Enjoy a large, bright bedroom and private bath. Guests have the whole second floor, and several have commented on how spacious the bedroom is--approx 18 x 18 ft. Air-conditioned, queen bed. Located in close-in St. Matthews, a quiet tree-lined area with easy access to downtown, major tourist attractions and eateries.

Staycation! Captain's Cabin: Historic Romantic
SUPERHOSTEntire cabin · 2 guests · 1 bed · 1 bathroom
Staycation! Captain's Cabin: Historic Romantic

Your own log cabin on a wooded hillside overlooking a private lake with gourmet breakfast served to your door (on weekends)! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! On most weekends, I offer a Cooking With Bourbon AirBNB experience that you are welcome to join.

What guests are saying:

“The captains cabin is truly a great place to visit to reset and enjoy the sound of nature and the peace and quiet. The cabin is spacious for 2 two people and the bathtub is very spacious! The cabin has a very rustic and vintage feel, but was very clean and sanitary. We spent our nights listening to rain outside by the porch or played dominos. Tammy and Jan were great hosts, very responsive, kind and friendly. They also have a Newfoundland named Captain, he is a very well behaved pup. Tammy made us breakfast every morning since it was the weekend and it was truly one of the highlights of our day. Tammy is a great cook/chef I definitely encourage to take her up on one of her cooking classes.”

Kentucky Derby Guest House
SUPERHOSTEntire guest house · 16+ guests · 6 beds · 1 bathroom
Kentucky Derby Guest House

The Kentucky Derby guest house ! We provide a great place to stay!

What guests are saying:

“What a beautiful space! It is so incredibly spacious and comfortable. Kati and Chad were super hospitable, easy to communicate with, and friendly. The area had 3 air conditioners, so it was very cool in there. It is also accessible for areas like Louisville or Bardstown. I had a great time and would absolutely stay again!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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Popular amenities for Simpsonville holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Simpsonville

The Sweet Spot!
SUPERHOSTEntire apartment
The Sweet Spot!
Price:₹12,225 / night
Private Pool & Hot Tub are open!
SUPERHOSTEntire guest suite
Private Pool & Hot Tub are open!
Price:₹13,592 / night
The Lakehouse at an Airstream resort in Derby City
SUPERHOSTEntire house
The Lakehouse at an Airstream resort in Derby City
Price:₹20,020 / night
Private Lower Level King Bed/Patio
SUPERHOSTPrivate room
Private Lower Level King Bed/Patio
Price:₹6,652 / night
Louisville's Hidden Gem
SUPERHOSTPrivate room
Louisville's Hidden Gem
Price:₹2,821 / night
Cute and quirky single apartment in St. Matthews
SUPERHOSTEntire flat
Cute and quirky single apartment in St. Matthews
Price:₹4,484 / night
Sky Blue Ensuite has a King bed and a balcony.
SUPERHOSTPrivate room
Sky Blue Ensuite has a King bed and a balcony.
Price:₹7,474 / night
Travelers quarters at Midlane Farm
SUPERHOSTPrivate room
Travelers quarters at Midlane Farm
Price:₹5,606 / night
Rustic apartment near the treetops
SUPERHOSTEntire loft
Rustic apartment near the treetops
Price:₹4,111 / night
AMAZING POOL HOUSE HOT TUB
SUPERHOSTEntire guest house
AMAZING POOL HOUSE HOT TUB
Price:₹7,634 / night
Park like setting!!
SUPERHOSTEntire guest suite
Park like setting!!
Price:₹5,242 / night
The Grace Airstream by the water in Derby City
SUPERHOSTCampervan/Motorhome
The Grace Airstream by the water in Derby City
Price:₹11,906 / night
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