Family-friendly holiday rentals in Simpsonville

Hidden Gem - Private Home - 3 BDRM In 5 Forks

Freshly renovated 3 bedroom home in highly sought after 5 Forks area. Beautiful space for family or multiple couples to enjoy inside or outside with open living and big back deck. Stay in and cook in our gorgeous kitchen that any woman would want to bring home with them OR go out and have many options at your fingertips on Woodruff Road. Come back to our comfortable queen sized beds in each bedroom and enjoy the peace and quiet of our home and 1.5 acre lot. Pet fee is required for furry friend

Indoor spaces · Kitchen · Amenities

Barndominium Getaway with Private Pool and Hot Tub

✨ Stunning New Construction Barndominium Poolhouse in Greenville, SC! 🏡 Experience the perfect blend of rustic charm & modern luxury in this newly built Barndominium GuestHouse! Thoughtfully designed, this space offers 1 bedroom 🛏️ + a pullout couch 🛋️, providing a comfortable and stylish stay. Free High-speed internet, 2 large covered patio’s offers a perfect spot to unwind, watch a game, cook dinner and enjoy the outdoors. 📺☀️. Back deck space available with new private jacuzzi hot tub.

Indoor spaces · Kitchen · View

Creative Oasis in Retro Airstream | wifi, AC, heat

Hola! So happy you found us. Come have your creative getaway in nature in our colorfully renovated 1972 Argosy Airstream. We didn't want you to have to squeeze into a tiny camper bathroom, so we made a brand new concrete/tile bathroom to give you extra space to get ready to explore the town in style. Private Roku tv in bedroom, wifi, coffee setup, books, AC/Heat, huge porch for relaxing. 25 minutes to downtown Greenville, near plenty of hikes and trails, or you can relax in nature at home :)

Indoor spaces · Kitchen · Decor

Luxury Retreat & Heated Pool Downtown Simpsonville

Luxury Pool House in the Heart of Simpsonville – Perfect for Gatherings! Designed for comfort, fun, and relaxation. 2 minutes from Downtown Simpsonville and 15 minutes from Downtown Greenville, this luxury retreat feels like a private resort with all the warmth of home. With nature views and countless amenities, you’ll have everything you need for an unforgettable stay. Up to 8 guests with 4 Spacious Beds and 2.5 Baths. Indoor & Outdoor Entertainment, Well-Equipped Kitchen, Cozy Living Room!

Family · Indoor spaces · Barbecue

Spacious 4 BR Escape w/ Fenced Yard Near Downtown

Welcome to your stylish retreat, conveniently located just 3 minutes from the shopping & dining in charming Downtown Simpsonville & convenient to everything that Greenville has to offer. With 4 bedrooms, 2 full baths & a fenced in yard, this house has everything you need for your stay. Located in a safe & quiet neighborhood just 20 minutes from downtown Greenville & 5 minutes to all of your daily needs. <B>Traveling with a large group? Ask about our other 4BR house across the street!<B>

Family · Kitchen · TV

Upstate Bungalow @ Five Forks

Small modern rustic studio located in a quiet neighborhood in the heart of Five Forks. Less than 1 mile from Woodruff Road for endless restaurant and shopping options. Also, just a quick drive to downtown Greenville, Simpsonville, and Mauldin. Perfect for locals or tourists to enjoy and explore all the Upstate has to offer! (Please note- there is an in-ground swimming pool that is not included in the listing/stay. It’s fenced and locked at all times. Signed liability waiver required).

Family · Kitchen · Hiking

Family home w/ PingPong & Playset-Central location

This is a very family friendly home with a playset, toys, and ping pong. It’s centrally located with all the shopping & restaurants you need just a couple miles away, and downtown Greenville is a 14 minute drive! The Millennium Campus and St. Francis Millennium Hospital are just a couple minutes away. The house is in a very safe neighborhood, with a nice walking trail nearby. It is a very comfortable and clean home that features all new mattresses, beds, washer, dryer, & much more!

Family · Indoor spaces · Cleanliness

Godfrey Suite is upstairs in Century Old Farmhouse

Come and relax in a peaceful setting on 6 acres amongst many oak trees.  Enjoy a cup of coffee on the front porch.  Private entrance with 2 bedrooms, 1 bathroom with walk-in shower, kitchenette/family room, TV with FireTVStick, free WiFi, books & games.  Kitchenette has small refrigerator with freezer, microwave, toaster oven and Keurig coffee maker. But no sink or stove . Coffee, creamer, sugar, water, paper products and plastic ware provided.  Parking is available on property.

Family · Kitchen · Amenities

2 Living Spaces -2800 ft.²- Sleeps 10

This spacious split-level house is in a quiet neighborhood and has plenty of room for 10 guests. Enjoy a king bed in the master bedroom, and 3 additional bedrooms, each featuring a queen bed. 2 single trundle beds are also available for the little ones. This home has space to gather everyone together or spread out and have some quiet time. Some fun features of this home are an outdoor fire pit, pool table, fenced backyard, deck with grill, and 3 smart TVs. 4 bedroom 3 bath home.

Family · Indoor spaces · Sleep quality

Five Forks' Best Kept Secret! 1 Bedroom Apt

This inviting 1 bedroom apartment in the popular Five Forks area is tucked away on a private, 7-acre property set back from the road. Our central location makes commuting a breeze. The ramp to the porch and private entrance as well as the handrail in the bathroom makes the home handicapped friendly. The apartment includes a well-equipped kitchen and thoughtfully appointed dining/living room, bedroom and bathroom. You will enjoy a hybrid mattress that will ensure restful sleep.

Family · Indoor spaces · Bathroom

Historic 3BR with Porch near Downtown

Welcome to The Southern Stoop – a newly refreshed, pet-friendly 3-bedroom, 1-bathroom home just a minute from Downtown Simpsonville and 20 minutes to Downtown Greenville. Enjoy a spacious lot with a screened-in porch and classic front stoop. Inside, find updated living spaces, a fully equipped kitchen, and comfortable bedrooms. Perfectly situated near local dining, shopping, and parks, it's your ideal base for a Southern getaway. We can't wait to host you!

Kitchen · Indoor spaces · Access

Water Oak Retreat / Comfy king bed, big back yard!

-Private deck with grill and eating area - Fully stocked kitchen with tea, coffee, basic cooking needs and snacks -Safe and quiet neighborhood -1 mile from all of downtown Simpsonville's shops and restaurants -1 mile to huge park with playground, tennis, pickleball, basketball, walking trail, and farmers market -Short 20 minute drive to downtown Greenville -Perfect for families and those traveling for work

Family · Indoor spaces · Cleanliness