Simpsonville Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Simpsonville vacation rentals

Bar (on property)

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (31 reviews)
"The VRBO was perfect. Has the elegant modern feel just like the pictures show and has lots of space to hang out and relax. Loved the location and how walkable it was to coffee shops, restaurants, and bars. Loved staying here and highly recommend!"
United States
Lucas L.
The price is ￥14,131
￥27,894 total
includes taxes & fees
May 5 - May 6
Unique Downtown Studio with an Industrial Vibe
Fridge, microwave, oven, stovetop

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
The price is ￥19,783
￥54,218 total
includes taxes & fees
May 5 - May 6
Quiet Downtown Maple Cottage Gem
Exterior

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (10 reviews)
"It was everything we needed."
United States
Carmen C.
The price is ￥12,011
￥62,419 total
includes taxes & fees
May 5 - May 6
St. Matthew’s - Walk to Shops & Restaurants
Fridge, microwave, oven, stovetop

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (13 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is ￥34,621
￥69,991 total
includes taxes & fees
May 4 - May 5
Beautiful restored Victorian farmhouse
Terrace/patio

Bourbon Trail Retreat: Hot Tub & Game Room

Bourbon Trail Retreat: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (24 reviews)
"We enjoyed our stay. It's a great cozy and comfortable place that's secluded and private. Iris was a great host. "
United States
Madison W.
The price is ￥34,542
￥96,553 total
includes taxes & fees
May 4 - May 5
Bourbon Trail Retreat: Hot Tub & Game Room
TV

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (19 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is ￥14,916
￥28,766 total
includes taxes & fees
May 19 - May 20
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Iron/ironing board, WiFi, bed sheets

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is ￥8,479
￥22,505 total
includes taxes & fees
May 11 - May 12
Alfesco - Walkable Highlands Guesthouse
Smart TV, books

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Clifton
10.0 out of 10, Exceptional, (33 reviews)
"Our stay was very pleasant, great location, lots of great restaurants. Tyler the host was was always available when we had an issue. "
United States
Max D.
The price is ￥13,346
￥32,986 total
includes taxes & fees
May 5 - May 6
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Exterior

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.6 out of 10, Exceptional, (23 reviews)
"This home is warm and cozy and close to everything we had planned."
United States
Dawn G.
The price is ￥14,837
￥35,993 total
includes taxes & fees
May 5 - May 6
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Interior

Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (19 reviews)
"Everything was outstanding!"
United States
John W.
The price is ￥27,979
￥43,228 total
includes taxes & fees
May 4 - May 5
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Fridge, microwave, oven, stovetop

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (17 reviews)
"House was cozy, and host was responsive. Rooms were clean and welcoming. A lovely place to stay."
United States
Alec S.
The price is ￥15,701
￥23,952 total
includes taxes & fees
May 12 - May 13
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Interior

Perfect Kentucky Derby stay near Churchill Downs!

Perfect Kentucky Derby stay near Churchill Downs!
Jeffersonville
The price is ￥14,228
￥36,946 total
includes taxes & fees
May 5 - May 6
Perfect Kentucky Derby stay near Churchill Downs!
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (38 reviews)
"This is a great little place to stay! Close to the Exposition Center and a lot of other attractions. It is an older place but clean and comfortable. This is our second stay at this place. "
United States
jaggers959
The price is ￥16,486
￥41,917 total
includes taxes & fees
May 10 - May 11
Close to Everything in Louisville!!!
Sauna

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (88 reviews)
"Very nice place"
United States
Seth B.
The price is ￥24,063
￥53,166 total
includes taxes & fees
May 5 - May 6
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Exterior

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (144 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is ￥40,038
￥63,057 total
includes taxes & fees
May 5 - May 6
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Smart TV, video games

Secretariat Twin Spires Suite!

Secretariat Twin Spires Suite!
Jeffersonville
8.8 out of 10, Excellent, (5 reviews)
"Very nice, clean, great location."
United States
Leigh
The price is ￥14,916
￥24,745 total
includes taxes & fees
May 5 - May 6
Secretariat Twin Spires Suite!
Exterior

The Adelyn, where comfort meets convenience

The Adelyn, where comfort meets convenience
Jeffersonville
10.0 out of 10, Exceptional, (7 reviews)
"Convenient to all Louisville destinations and downtown Jeffersonville "
United States
Ron R.
The price is ￥19,359
￥48,666 total
includes taxes & fees
May 5 - May 6
The Adelyn, where comfort meets convenience
Fridge, microwave, oven, stovetop

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, (19 reviews)
"Beautiful home and surroundings!"
United States
Peg H.
The price is ￥34,253
￥82,658 total
includes taxes & fees
Jun 2 - Jun 3
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Interior

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"Amazing host! Great place to stay."
United States
Robert M.
The price is ￥21,196
￥37,359 total
includes taxes & fees
May 4 - May 5
Carriage House, 7 minutes from downtown Louisville
Living area

Stylish House Walking Distance from the Fun of the Highlands!

Stylish House Walking Distance from the Fun of the Highlands!
Phoenix Hill
9.4 out of 10, Exceptional, (32 reviews)
"We will stay here over and over again. It’s a lovely place that a perfect location."
United States
Jennifer H.
The price is ￥7,772
￥27,246 total
includes taxes & fees
May 4 - May 5
Stylish House Walking Distance from the Fun of the Highlands!
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

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

10/10 Excellent
"Friendly staff went above and beyond"
Brandon 2-night trip
Posted 1 hour ago
Holiday Inn Louisville Airport South by IHG

Find out more about Simpsonville

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Look no further and take a look at our great range of rental properties in Simpsonville!

Frequently asked questions

Can I find a vacation rental in Simpsonville?

Yes, you can find vacation rentals near the most popular local attractions in Simpsonville, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Simpsonville?

Charming home in the heart of the city!: This vacation home rental outside of Simpsonville is equipped with a selection of games, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Simpsonville?

Choose from 10 Expedia vacation rentals in Simpsonville for a memorable vacation.

What’s there to see and do in Simpsonville?

While exploring the area, visit family-friendly sights like Louisville Zoo, or get outside and enjoy nature at Beckley Creek Park. The Outlet Shoppes of the Bluegrass and Whitney M. Young, Jr. Birthplace are other places to visit while you're in town.

What’s a vacation rental in Simpsonville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Simpsonville. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.