Family-friendly holiday rentals in Simpsonville

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!

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>

Carolina's Olde Mill, family friendly

Your family will be close to everything when you stay at this centrally-located house. New 2023 build in a quiet neighborhood, 1 mile from downtown Fountain Inn and 18 miles to Greenville. Just 2 blocks from Interstate 385. Olde Mill is located only a few miles to Walmart, grocery store, restaurant's and shopping. Spacious place to unwind after a day of exploring or stay in and play cards/board games provided. Hot out... let kiddos run thru the sprinkler! Enjoy grilling on covered deck.

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 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!

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.

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.

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.

The Belle is lovely in the fall

Experience this thoughtfully designed hidden retreat nestled in a wooded setting with all the comforts of home. Enjoy the charm of the outdoors on your private porch in peaceful surroundings. Return from shopping, sightseeing or work to The cozy comfortable Belle. Outside grilling, picnic area, fire pit, porch sitting or swing. It’s all waiting for your pleasure. 20 min downtown Greenville 20 min Bon Secours Wellness Area 10 min downtown Greer 10 min The Pavillion

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!

Willow Oak Retreat // Comfy beds & Large backyard!

Welcome to Willow Oak Retreat! We cant wait to host you! - Private deck with grill and eating area - Fully equipped kitchen with tea, coffee and snacks - Safe and quiet neighborhood - 1 mile to all of downtown Simpsonville's restaurants and shops - 1 mile to huge park including playground, tennis, pickleball, walking trail, basketball and farmers market. - Short 20 minute drive to downtown Greenville - Perfect for families and those traveling for work!

Spacious 3 BR house with private backyard.

Welcome to our peaceful retreat! Nestled in a quiet corner, our cozy Airbnb features a charming fire pit for evening relaxation, a screened-in porch perfect for sipping your morning coffee or unwinding in the evening, and a fenced-in backyard for added privacy and comfort. Plus, enjoy the fun of our pool during warm weather. We hope you enjoy a tranquil stay filled with warmth and relaxation.