Simpsonville Vacation Rentals

Vacation Rentals in Simpsonville

Property grounds
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
10.0 out of 10, Exceptional, (173)
"We stayed at this property for 5 nights. Perfect size for the 3 of us. Hot tub was awesome. Everything was provided from trash bags to soaps and shampoos. The neighborhood was quiet. A great place to get a way from it all and explore Kentucky!!!"
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Exterior
Captain's Cabin Bed & Breakfast: Historic & Romantic
10.0 out of 10, Exceptional, (113)
"This location was exactly as described. It was one of most interesting and quite different from the average property. If you like the feel of a rustic cabin in the woods with amazing scenery, then this is a great spot. The hosts were incredibly hospitable and kind. The house has all of the basic needs and more. I appreciate being able to experience this one."
The price is $247
$387 total
includes taxes & fees
Jun 3 - Jun 4
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, (18)
"Wanted to find a place to gather with friends for a long fireside chat to catch up. We all loved this quiet setting and that hug of a cabin with its sweet appointments. So grateful our hosts created such a special place! Loved having time with my friends there."
The price is $133
$169 total
includes taxes & fees
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, (64)
"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 $102
$211 total
includes taxes & fees
May 20 - May 21
Stay at Re-Nu: Unique Shipping Container Apartments in NuLu
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 $699
$1,322 total
includes taxes & fees
May 20 - May 21
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 $399
$666 total
includes taxes & fees
May 21 - May 22
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 $45
$145 total
includes taxes & fees
May 19 - May 20
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, (112)
"Southern hospitality at its best! Our host welcomed us with a wonderful local goodies basket. To my surprise the clear ponchos that I had left at home to attend the Derby were included! We had 4 ladies in our group and the beds and accommodations were perfect. There’s even a backyard patio to enjoy with a zen garden. This is a spacious Victorian beautifully remodeled with all hard wood floors. Everything was clean and very well stocked. We were able to walk downtown during the day and Uber home...
The price is $110
$192 total
includes taxes & fees
May 28 - May 29
★ 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 $70
$180 total
includes taxes & fees
May 28 - May 29
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)
"We had a great time during our stay. Our entourage included my husband and I, 3 teenagers plus 2 large dogs. It was the perfect size for sleeping, but a little tight for hanging out unless you hang out outside on the hige deck over the river. The furniture is college dorm style, but works for the purposes we needed. All in all it is a cute little house and a great location."
Family/Pet-Friendly Riverside Home w/Amazing Views
Property grounds
Stunning Victorian Home - prime location minutes from Louisville
9.8 out of 10, Exceptional, (13)
"We stayed at this property with a group of guys for a bourbon tour weekend. The property is located just outside Louisville and was only a 10 dollar Uber downtown (or 10 minute drive). If you have time, there is also an extremely cool walking bridge to Louisville. The property is well-maintained and fit all of our needs. We especially enjoyed that backyard and spent a number of hours hanging out, playing yard games and grilling back there. Communication with the host Amy was excellent. An...
Stunning Victorian Home - prime location minutes from Louisville
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 $114
$185 total
includes taxes & fees
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)
"While, we didn't get too spend a lot of time at the house, while we were there - was great! It is such a cute little house, that has been totally updated! We loved the unique setup of the house! The kitchen, in the basement, was fun! We will definitely check to see if this house is available when we return for Nationals, again next year!"
River City Retreat close to the Zoo/Expo/Airport/Churchill
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 $90
$245 total
includes taxes & fees
May 20 - May 21
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
Outdoor dining
Cute, Chic, Pet Friendly Bungalow By St. Matthews!
9.4 out of 10, Exceptional, (25)
"Great location and nice secure backyard for the dogs. We enjoyed our stay."
The price is $137
$340 total
includes taxes & fees
May 21 - May 22
Cute, Chic, Pet Friendly Bungalow By St. Matthews!
Property grounds
Ultra Modern in NuLu|Hot Tub|Fire Pit|King Bed
9.4 out of 10, Exceptional, (19)
"We had a wonderful stay in Louisville. Our home was just as it was described in the listing. The house was perfectly located near shopping, restaurants, breweries, downtown. . . . Our hosts were very responsive and it was a super easy check in and check out process. We would recommend this property to anyone coming to visit Louisville - in fact, we already have."
The price is $190
$515 total
includes taxes & fees
Jun 3 - Jun 4
Ultra Modern in NuLu|Hot Tub|Fire Pit|King Bed
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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.

Simpsonville Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Simpsonville private vacation homes
Known landmarks
Talon Winery, Shelby County Community Theatre and Beckley Creek Park
International airport
Louisville, KY (SDF-Louisville Intl.)

Other types of properties in Simpsonville you may be interested in

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, (410)
"Very clean and spacious room. Staff were excellent! If I had to say anything negative it would be the lack of a coffee before 8am."
The price is $109
$128 total
includes taxes & fees
May 19 - May 20
Derby City Gaming & Hotel - A Churchill Downs Property
Restaurant
Hotel Genevieve
4.0 star property
9.2 out of 10, Wonderful, (285)
"I loved absolutely everything about this charming boutique hotel. The rooms were immaculate and I loved the décor. Bathrooms were large and gorgeous as well. The location was probably my favorite aspect of the hotel as it was mere minutes walking to some amazing restaurants. Will definitely make this my hotel of choice whenever I visit Louisville. "
The price is $158
$185 total
includes taxes & fees
Jun 16 - Jun 17
Hotel Genevieve
Interior
Crowne Plaza Louisville Airport Expo Center, an IHG Hotel
3.5 star property
7.6 out of 10, Good, (1004)
"Delightful location convenient to everything"
The price is $107
$126 total
includes taxes & fees
May 20 - May 21
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.

Everything you need to know about Simpsonville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpsonville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpsonville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpsonville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpsonville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Simpsonville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $45 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpsonville rentals

At Expedia, we put the best Simpsonville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Simpsonville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpsonville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpsonville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

5/5 Excellent
"Very clean and spacious room. Staff were excellent! If I had to say anything negative it would be the lack of a coffee before 8am."
A verified traveler stayed at Derby City Gaming & Hotel - A Churchill Downs Property
Posted 1 day ago
Derby City Gaming & Hotel - A Churchill Downs Property