Family-friendly holiday rentals in Simpsonville

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 :)

The Belle a Cozy Hideway

The Belle is nestled in a wooded setting with all the comforts of home and tastefully decorated. Push pause and enjoy coffee and breakfast outside on your private porch in peaceful surroundings. If you are a Pickleball fan a new 18 court complex has been built 1 mile from The Belle. Enjoy shopping, sightseeing or work then return to the comfort of The Belle. Grill, picnic area, fire pit, or porch sit. It’s all waiting for your enjoyment. 20 min downtown Greenville 10 min downtown Greer

Teeny House (monthly discounts)

Designed for the solo traveler (no more than one person allowed), this micro space is an 8'x12' free standing teeny house with just enough room for a twin bed and a bathroom with a 36" square shower, a sink and toilet. In the hospitality world, this is called a “layover”— a comfortable, one person spot to rest your head and a clean, hot shower. Located between 2 other Airbnbs on the same property, so you will likely see other guests coming and going, but the space is completely private.

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. 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.

70's Nostalgia

Go back to a simpler time in this totally restored 1969 Concord Traveler at Kingfish Farms. Located just a mile and a half from the quaint town of Woodruff, SC. and a little over 2 miles from I-26. Our 20 acre farm gives you plenty of room to enjoy the outdoors and get back to nature. Relax and rejuvenate in our traditional Finnish sauna and outdoor shower. Take a walk through our wooded trail and visit the goats and pigs. Enjoy the covered front porch, fire pit, and grill.

Private Suite in Downtown Simpsonville

Cozy 1 bed/1 bath apartment in downtown Simpsonville. With this private single unit above a garage used for storage only, you do not share walls with anyone! You are within walking distance to restaurants & shopping! This private unit is a rare find for the price!! As you pull into your own parking space, you overlook a private yard. ***Please note there is a train near the home that runs once midday and once late at night.

Tiny House in the Country

Escape to the country and relax in this cozy tiny house in Fountain, SC. This charming space features one full bed, a bathroom with shower, microwave, and refrigerator. Enjoy the peace and quiet of the countryside, or explore the nearby towns and attractions. Perfect for a secluded romantic getaway, music festival trip, or just visiting! Book your stay today and experience the simple life in a tiny house in the country!

Sally's Cottage

Couples retreat located 6 miles from downtown Greenville and the Swamp Rabbit Trail in a comfortable country setting. Wake up to a beautiful woods view through a large bay window and wildlife that surrounds the cottage (deer, birds and squirrels). Experience the beauty of the country in the city! Enjoy the eclectic collection of art and design in this cute little cottage.

Cozy Pet-Friendly Home | Near Greenville & I-85

You’ll love staying here because it’s the perfect mix of comfort, privacy, and charm. Whether you’re relaxing by the fire pit, enjoying the peaceful outdoor space, or unwinding inside with all the comforts of home, this cozy retreat offers everything you need for a relaxing and memorable stay. Plus, it’s pet-friendly and located in a quiet neighborhood close to everything!

Upscale Tiny Home close to downtown Greenville

Enjoy a tiny space that creates huge memories. 15 mins from GSP Aiport and downtown Greenville. There's soo much to do, you'll barely have a chance to enjoy free WiFi. Enjoy a day exploring Paris Mountain State Park, Bon Secours Wellness Arena, Falls Park on the Reedy, or shopping at Haywood Mall or Greenridge. Also, check your travel dates for a ballgame at Fluor Field.

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

-Private deck with grill and eating area - Fully stocked kitchen with tea, coffee 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, basketball, and farmers market -Short 20 minute drive to downtown Greenville -Perfect for families and those traveling for work