Simpsonville Vacation Rentals

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Vacation Rentals in Simpsonville

Property grounds
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
10.0 out of 10, Exceptional, (176)
"Please don’t hesitate in booking this property. It was immaculate and the amenities far exceeded other properties I have stayed at. Plenty of paper products, towels and kitchen supplies. The owner has supplied everything you need, even throw blankets for the sofas when you want to cozy up in the cute living room. The king bed was extra comfy. Would absolutely stay here again."
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Exterior
Captain's Cabin Bed & Breakfast: Historic & Romantic
10.0 out of 10, Exceptional, (113)
"Beautiful, well maintained cottage. We loved it! We wished we could have stayed longer. Very close to local activities and the airport."
The price is ￥39,068
per night
Jun 4 - Jun 5
Captain's Cabin Bed & Breakfast: Historic & Romantic
Property grounds
Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!
10.0 out of 10, Exceptional, (20)
"We enjoyed our time getting out in the countryside for the weekend. It was peaceful and beautiful!"
The price is ￥20,701
per night
Jun 4 - Jun 5
Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!
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Fridge, microwave, oven, stovetop
BOOK NOW FOR DERBY! Bourbon Trail/Parks Easy access to Downtown w/Pool/Firepit
10.0 out of 10, Exceptional, (65)
"We really enjoyed the stay and the property was great. We would definitely stay here again"
BOOK NOW FOR DERBY! Bourbon Trail/Parks Easy access to Downtown w/Pool/Firepit
Fridge, oven, stovetop, dishwasher
Stay at Re-Nu: Unique Shipping Container Apartments in NuLu
10.0 out of 10, Exceptional, (9)
"My wife wants to stay at a place like this everehere"
The price is ￥16,502
per night
May 27 - May 28
Stay at Re-Nu: Unique Shipping Container Apartments in NuLu
Fridge, microwave, oven, stovetop
Ultimate Bourbon Experience in Heart of Louisville
10.0 out of 10, Exceptional, (4)
"The property was clean and cute. It was a bit small for 4 adults but manageable."
Ultimate Bourbon Experience in Heart of Louisville
Fridge, microwave, oven, stovetop
RIVERFRONT - Boat Slips - 10 Min to Dtown Lville
10.0 out of 10, Exceptional, (110)
"This property boasts everything it says it does and comes with great neighbors too! I stayed with my two teen kiddos and we had so much fun that we didn't have to leave the property for most of our stay. The games/amenities provided kept us busy and comfortable. My son just fished and fished and fished and even cooked us up a catfish or two. My daughter loved the volleyball net and many other games provided."
RIVERFRONT - Boat Slips - 10 Min to Dtown Lville
Fridge, microwave, oven, stovetop
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
9.8 out of 10, Exceptional, (53)
"My group of 8 had an excellent time time at the house. There were ample beds for all to have their own private room and many additional beds to spare. The space is a wonderful historical mansion, with clearly several additions over the years. The outdoor spaces are sensational! Great destination for a big group!"
The price is ￥108,799
per night
May 28 - May 29
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Exterior
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
9.8 out of 10, Exceptional, (186)
"Absolutely beautiful and very peaceful! Lots of room to accommodate family and friends! Could not have been a more perfect weekend!"
The price is ￥62,104
per night
May 22 - May 23
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
Smart TV, books
Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries
9.8 out of 10, Exceptional, (28)
"This was exactly as pictured- so cozy and so close to town. It was a great place to stay with a few friends!"
The price is ￥7,783
per night
May 27 - May 28
Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries
Fridge, microwave, oven, stovetop
★ Victorian Louisville ★ Large 1200 sqft APT #1
9.8 out of 10, Exceptional, (113)
"This was a great place to stay for our trip to the PGA Tournament. Easy access to interstate and close to downtown and U of L. Street parking was always available. The unit has lots of charm and everything you need for your stay. Our host was great with his communication and the check-in/check-out process couldn’t have been easier."
The price is ￥17,122
per night
Jun 4 - Jun 5
★ Victorian Louisville ★ Large 1200 sqft APT #1
Fridge, microwave, oven, stovetop
Cozy Bourbon Speakeasy Themed Loft - Minutes from Downtown!
9.8 out of 10, Exceptional, (23)
"The place was very nice and clean. Would definitely stay again"
The price is ￥9,376
per night
May 27 - May 28
Cozy Bourbon Speakeasy Themed Loft - Minutes from Downtown!
Exterior
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
9.8 out of 10, Exceptional, (36)
"We've joined together for Thanksgiving for several years and this was by far the nicest place. My only complaint would be the ice maker didn't work. We hope to visit again!"
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Property grounds
Family/Pet-Friendly Riverside Home w/Amazing Views
9.8 out of 10, Exceptional, (11)
"Great view"
Family/Pet-Friendly Riverside Home w/Amazing Views
Front of property
Stellar Suites
4.5 star property
9.6 out of 10, Exceptional, (68)
"I have enjoyed my stays at Stellar Suites. "
The price is ￥18,590
per night
Jun 5 - Jun 6
Stellar Suites
Fridge, microwave, oven, stovetop
River City Retreat close to the Zoo/Expo/Airport/Churchill
9.6 out of 10, Exceptional, (35)
"The hosts went above and beyond making our stay a great experience. We stayed for the Kentucky Derby and the hosts left Kentucky Derby items for us to take home, ponchos in case it rained, the fridge and freezer were stocked, and a snack basket was left out with a hand-written welcome card. Additionally, they accommodated our requests and responded in a timely manner. I have stayed several places in the past and can say without a doubt that this was the best experience due to the exceptional...
River City Retreat close to the Zoo/Expo/Airport/Churchill
Interior
Quiet and Quaint Carriage House: Sabai Sabai
9.6 out of 10, Exceptional, (5)
"This property suited our needs. It was clean and close to our destination. Quiet neighborhood."
The price is ￥6,407
per night
May 22 - May 23
Quiet and Quaint Carriage House: Sabai Sabai
Fridge, microwave, oven, stovetop
Couples Cozy Lake Cottage at Edgewater Resort 36
9.6 out of 10, Exceptional, (37)
"I booked this place for my BIL’s 40th. Three nights. It was 6 adults, 3 couples. We could not ask for a more centrally located place. Easy drives to all the great distilleries. But out of the way and peaceful. The views of the lake driving in were amazing. We saw deer and a turkey. You can’t quite see the lake but it’s so pretty from the back deck. When we arrived one of the bathroom showers wouldn’t stop running. I messaged the property manager and she and the owner got back to me right away....
Couples Cozy Lake Cottage at Edgewater Resort 36
Exterior
Close to Everything in Louisville!!!
9.4 out of 10, Exceptional, (25)
"Great"
The price is ￥14,009
per night
May 28 - May 29
Close to Everything in Louisville!!!
Property grounds
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
9.4 out of 10, Exceptional, (22)
"Yearly my wife and I get away just to enjoy our time together. This is the second year in a row we stayed at this location and we are planning on next year already. The cabin is so relaxing and the host is outstanding in communicating with us before our arrival. This is the place to be. Thank you for an enjoyable time."
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
Don't see what you're looking for?
See all available properties in Simpsonville
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.

Other types of properties in Simpsonville you may be interested in

Restaurant
Hotel Genevieve
4.0 star property
9.2 out of 10, Wonderful, (292)
"Very nice hotel. Funky retro furnishings. Great rooftop bar. Lots of dining options in the area. Very walkable. Would definitely stay here again when in Louisville. "
The price is ￥27,972
per night
Jun 16 - Jun 17
Hotel Genevieve
Premium bedding, in-room safe, desk, laptop workspace
Derby City Gaming & Hotel - A Churchill Downs Property
4.0 star property
9.2 out of 10, Wonderful, (420)
"Comfortable rooms, minimal noise, would recommend."
The price is ￥14,941
per night
Jun 3 - Jun 4
Derby City Gaming & Hotel - A Churchill Downs Property
Interior
Crowne Plaza Louisville Airport Expo Center, an IHG Hotel
3.5 star property
7.6 out of 10, Good, (1015)
"It was clean. Quiet rooms. In the middle of remodeling. We got an updated room but you can tell it was recently redone. We could smell the faint fumes of paint and in the back was all their old furniture. But def not decent enough for the price."
The price is ￥16,063
per night
May 24 - May 25
Crowne Plaza Louisville Airport Expo Center, an IHG 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.

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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?

One room rent: This vacation home rental outside of Simpsonville has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Simpsonville?

Choose from 7 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.

Recent reviews of Simpsonville properties
Expedia verified reviews

Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

5/5 Excellent
"Stay was great! Clean and friendly "
A verified traveler stayed at Wingate by Wyndham Louisville Fair and Expo
Posted 1 day ago
Wingate by Wyndham Louisville Fair and Expo