Family-friendly vacation rentals in Simpsonville

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.

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>

Upscale cottage in Downtown Fountain Inn

All new cottage/studio apartment. 5 minutes to CCNB amphitheater at Heritage Park, 10 minutes to downtown Simpsonville, 25 minutes to Bon Secours Wellness Arena in downtown Greenville. 20 minutes from GSP airport. Close to Hillcrest Hospital and Bon Secours in Simpsonville. 25 minutes from Presbyterian College, 30 minutes from Furman University. Guest have access to partially fenced backyard as well as full access to private cottage. Host lives on property! There is NO Bathroom Door.

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.

Simple Circle Cottage - Quiet. Quaint. Close.

Just 3 blocks from the heart of downtown Simpsonville - come enjoy all that our charming town has to offer without giving up the peace & quiet of a country retreat! Walk to a variety of small retail shoppes and restaurants including Southern-style BBQ, Mexican, Thai, Pizza, authentic crêpes, gourmet coffee, ice cream and more! The police & fire stations are within 1 block, as well as City Park. 3 min to Heritage Park Amphitheater <15 min to downtown Greenville 20 min to GSP AIrport

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).

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.

Relaxing Cottage near downtown S’ville

Relax with the whole family in this 3 bed/2 bath spacious cottage. Whether sitting in the chair hammocks on the back porch or cozying up around the campfire, you will love the little spaces around this house for relaxing or being together. The Brentwood Cottage is only minutes from I-385, downtown Simpsonville, and about 25 minutes from the heart of downtown Greenville and all that it has to offer. It is close to restaurants, shopping, Target, grocery stores, and the like.

The Belle a Lovely Southern glamper

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!