Simpsonville vacation rentals

We found 134 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Simpsonville that are perfect for your trip. Vacation homes offer the amenities you expect for your family, friends, or furry companion, like WiFi and a washer and dryer. At the end of the day, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

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Find out more about Simpsonville

Why visit Simpsonville

  • Outdoor Recreation: Enjoy the picturesque Beckley Creek Park, perfect for hiking, picnicking, and family outings.
  • Proximity to Louisville: Benefit from Simpsonville's convenient location near Louisville, offering a vibrant urban experience.
  • Family-Friendly Atmosphere: Explore charming neighborhoods and engage in activities suitable for all ages.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including private homes, apartments, and condos.
  • Seasonal Events: Experience the lively summer nights and local events that create a festive community spirit.

Popular types of accommodation in Simpsonville

Planning a getaway to Simpsonville? The excitement begins with finding the perfect place to stay. Explore our top choices for vacation rentals, including private homes, apartments, and condos. Whether you're searching for affordable rentals or a spacious home with a full kitchen, we’ve got you covered. Browse available rental homes and discover ideal options that fit your needs, ensuring a memorable stay in this charming town.

  • Houses: The top choice for visitors to Simpsonville, these spacious homes offer a perfect base for families or friends seeking comfort and privacy.
  • Apartments: A popular option for travelers, apartments provide convenience and a home-like atmosphere for those exploring the area.
  • Condos: Ideal for those wanting a blend of luxury and practicality, condos are a favored rental choice in Simpsonville.
  • Cottages: These quaint and charming rentals offer a cozy ambiance, perfect for a romantic getaway or a peaceful retreat.
  • Cabins: For a rustic experience, cabins are a delightful option, allowing guests to immerse themselves in nature.**

Top attractions near Simpsonville

Simpsonville, Kentucky, offers an ideal vacation spot for families and business travelers alike, featuring a blend of urban parks, lakes, and recreational parks. Visitors can enjoy a variety of outdoor activities and family-friendly experiences, making it a perfect destination for those seeking both city excitement and natural beauty. Whether you're planning a short getaway or an extended stay, there's plenty to explore in and around this charming town.

  • Beckley Creek Park: This urban park offers a vibrant outdoor experience with ample space for family activities, walking trails, and picturesque picnic spots, all set against a backdrop of city life.
  • Yew Dell Botanical Gardens: A romantic escape, this botanical garden features stunning landscapes, diverse plant collections, and tranquil walking paths, perfect for families and nature lovers alike.
  • Southeast Christian Church: A culturally rich environment, this church is known for its welcoming community and inspiring architecture, making it a significant landmark in the area.

Things to do recommended for couples

Looking for a romantic getaway in Simpsonville? Enjoy a luxurious round of golf at Valhalla Golf Club, just 7 miles away. Then, savor the ambiance at Talon Winery, 5 miles away, or explore the enchanting Milla Nova Winery, 18 miles away, for a delightful experience together.

Things to do recommended for families

Families visiting Simpsonville can enjoy a day of fun at IceLand Sports Complex for ice skating, race at Bluegrass Indoor Karting, or embark on an exciting adventure at Danger Run arcade. Each location offers thrilling experiences that are perfect for family bonding and entertainment.

Things to do recommended for groups

Experience a day of shopping at The Outlet Shoppes of the Bluegrass, where you can enjoy family-friendly entertainment. For outdoor enthusiasts, play a round at Long Run Golf Course or Persimmon Ridge Golf Club, both offering stunning landscapes just a short drive from Simpsonville.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Simpsonville

When planning your trip, whether you're traveling with a group, family, pets, or looking for extended stays, be sure to use filters that align with your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Simpsonville with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, Vrbo allows you to filter for these options and many more.
  • Traveling to Simpsonville with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Simpsonville: For many families, a vacation isn't truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and beds, ensuring that both you and your pets feel comfortable and at home.
  • Planning for a long term stay visiting Simpsonville: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Simpsonville

Simpsonville, Kentucky, offers a delightful blend of family-friendly attractions and charming neighborhoods. Explore the picturesque Beckley Creek Park for outdoor recreation, or enjoy the vibrant atmosphere during summer nights. With its prime location near Louisville, you'll find a mix of cozy family homes and some pricier neighborhoods, perfect for both relaxation and business-themed visits. Whether you're seeking romance or friendly encounters, Simpsonville is a wonderful destination to create lasting memories.

  • Louisville: As a vibrant metropolis, Louisville is known for its rich culture and engaging outdoor experiences. Located adjacent to Simpsonville, this city offers a variety of attractions for families, business travelers, and outdoor enthusiasts alike. Explore the expansive shopping mall centers, unwind in recreational areas, or catch a live music concert at one of the many venues. Key landmarks include an event conference venue and a convention center, ideal for business travelers, along with beautiful lakes perfect for a relaxing day by the water.
  • Finchville: Just 4 miles from Simpsonville, Finchville is a charming city that caters to those seeking outdoor adventures and romantic getaways. Visitors will find delightful shopping centers and recreational areas that provide ample opportunities for entertainment and relaxation. Nearby attractions include a picturesque lake, a versatile event conference venue, and the stunning national state park, making Finchville a perfect stop for nature lovers and couples looking for a peaceful retreat.
  • Shelbyville: Located 7 miles from Simpsonville, Shelbyville is a welcoming city ideal for family outings and romantic excursions. The city boasts several shopping mall centers and recreational areas, ensuring there's something for everyone to enjoy. Key attractions include a lovely lake for outdoor activities, an event conference venue for any business needs, and a visitor center that offers insights into the local culture and history. Shelbyville's charm makes it an excellent addition to your travel itinerary.

Best time to go to Simpsonville

If you're planning a trip to Simpsonville, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March and June to July, while off-peak times, like January, May and August tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.7°F (0.4°C)Light RainMostly CloudySlightly LowSlightly Low
February36.3°F (2.4°C)Light RainMostly CloudyAverageSlightly Low
March45.7°F (7.6°C)Light RainMostly CloudySlightly HighAverage
April55.2°F (12.9°C)Light RainMostly SunnyAverageSlightly High
May65.1°F (18.4°C)Light RainMostly SunnySlightly LowSlightly High
June73.2°F (22.9°C)Light RainMostly SunnySlightly HighAverage
July76.5°F (24.7°C)Light RainMostly SunnySlightly HighAverage
August75.0°F (23.9°C)Light RainMostly SunnySlightly LowAverage
September69.3°F (20.7°C)Light RainMostly SunnyAverageSlightly High
October57.6°F (14.2°C)Light RainMostly SunnyAverageAverage
November45.3°F (7.4°C)Light RainMostly SunnyAverageAverage
December38.5°F (3.6°C)Light RainMostly CloudyAverageSlightly Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. By enrolling in our travel rewards program, One Key, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up where you left off, or manage your travel plans with ease. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Simpsonville getaway

Learn about the unique charm of Simpsonville with a stay in a private vacation home. This city has something for everyone. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Simpsonville

Are you searching for things to do in the area? Venture out of your cozy vacation rental and check out everything that makes Simpsonville a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Valhalla Golf Club (7.1 mi / 11.4 km)
  • Louisville Zoo (19.4 mi / 31.2 km)
  • Talon Winery (4.5 mi / 7.3 km)
  • Polo Fields Golf and Country Club (6.1 mi / 9.9 km)
  • Danger Run (12.6 mi / 20.3 km)
  • Milla Nova Winery (18 mi / 29 km)

Exploring the natural features in Simpsonville

Whether you're looking for adventure or just want to take in the scenery, Simpsonville is a great place to get outside. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Beckley Creek Park (6.8 mi / 11 km)
  • Yew Dell Botanical Gardens (10.8 mi / 17.4 km)
  • Ohio River Valley (12.3 mi / 19.7 km)
  • E.P. Tom Sawyer State Park (12.5 mi / 20 km)
  • Taylorsville Lake State Park (13.5 mi / 21.7 km)
  • Taylorsville Lake (15.9 mi / 25.6 km)

Transportation options to and around Simpsonville

The nearest airport is in Louisville, KY (LOU-Bowman Field), located 17.3 mi (27.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Louisville Intl. Airport (SDF), which is 21.4 mi (34.5 km) away.

Frequently asked questions

What is the best area to stay in Simpsonville, Kentucky, United States of America when booking a vacation rental?
When considering a vacation rental in Simpsonville, Kentucky, the area around the historic downtown is a fantastic choice. This charming neighborhood offers a blend of small-town warmth and accessibility to local attractions. One of the highlights nearby is the serene and picturesque Simpsonville Park, where visitors can enjoy walking trails and green spaces superb for picnicking or leisurely strolls. Additionally, the proximity to the famous Shelbyville Horse Show adds an exciting cultural dimension to your stay, especially for horse enthusiasts.

Another great option is the area near the Outlet Shoppes of the Bluegrass, which is not only a shopping haven but also a delightful spot for dining and entertainment. The variety of vacation rentals available here ensures that you'll find accommodations that suit your needs, whether you're traveling with family or seeking a cozy getaway.
How much does it cost to rent a vacation home in Simpsonville?
Prices for vacation rentals in Simpsonville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Simpsonville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Simpsonville vacation house rentals?
You can find great discounts on house rentals in Simpsonville on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Simpsonville?
In Simpsonville, vacation houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties often feature spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many vacation houses come with outdoor spaces such as decks or patios, offering a place to relax and enjoy the surrounding natural beauty. Cottages, on the other hand, provide a charming and cozy atmosphere, often situated in quieter neighborhoods that allow for a peaceful retreat.
Are there any family house rentals in Simpsonville?
In Simpsonville, Kentucky, there are several family-friendly house rentals available, making it an excellent choice for those traveling with children. Many of these homes are spacious, offering multiple bedrooms and comfortable living areas for family gatherings. Visitors can expect amenities such as fully equipped kitchens, which are superb for preparing meals together, as well as outdoor spaces where kids can run and play.

The town is conveniently located near attractions like the Kentucky Horse Park and the picturesque parks in the surrounding area, providing opportunities for outdoor activities and family outings.
Can I find long-stay vacation rentals in Simpsonville?
A long-stay vacation rental in Simpsonville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Simpsonville?
In Simpsonville, Kentucky, there are several vacation rentals suitable for remote work. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi and dedicated workspaces, including desks and ergonomic chairs, which are conducive to productivity. Travelers can expect comfortable living environments that allow for both work and relaxation, often featuring spacious interiors and cozy settings.

The town's proximity to local attractions, such as the serene parks and the picturesque rural landscape, provides a refreshing break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Simpsonville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Simpsonville with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Simpsonville?
In Simpsonville, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals conveniently. Many rentals offer onsite parking, making it easy for travelers to arrive by car. A coffee and tea maker is typically available, providing a nice touch for morning routines. Additionally, most properties feature decks or patios, superb for enjoying the outdoors and relaxing after a day of exploring. Many rentals also include a desk, suiting those who may need a workspace during their stay.
When is the best time to visit Simpsonville for a vacation rental?
The best time to visit Simpsonville for a vacation rental is during the peak summer months of June through August, with July being the most popular month. This vibrant season draws families and travelers looking to enjoy the warm Kentucky weather, where temperatures typically range from the mid-70s to low 90s Fahrenheit. It's an ideal time for outdoor activities, such as exploring local parks, attending summer festivals, and sampling delicious food at lively outdoor markets.

Simpsonville has an inviting space, with plenty of opportunities for sightseeing and relaxation. The summer months provide a great backdrop for enjoying the scenic beauty of the area, whether you're strolling through charming neighborhoods or visiting nearby attractions.

For those seeking a budget-friendly option, consider visiting in January. This quieter month allows for a more tranquil experience, superb for cozying up in a rental and enjoying the slower pace of winter in Simpsonville.
How early should I book a Simpsonville vacation rental?
Book your Simpsonville vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Simpsonville, Kentucky, United States of America?
In Simpsonville, Kentucky, visitors can explore several attractions that highlight the local charm. The town is known for its proximity to the Kentucky Bourbon Trail, where travelers can visit nearby distilleries and experience bourbon tastings. The picturesque Main Street is lined with quaint shops and restaurants, great for leisurely strolls and dining experiences.

Just a short drive away, the expansive Red Orchard Park offers walking trails, picnic areas, and a playground, making it an ideal spot for families and outdoor enthusiasts. For those interested in history, the nearby Kentucky Railway Museum in neighboring New Haven provides insights into the region's railroad heritage.
Can I change or cancel my Simpsonville home rental booking on Vrbo?
To find Simpsonville vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Simpsonville vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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