Holiday rentals in Simpsonville

Safe Solo Suite | Desk & Kitchen | Greenville SC

Welcome to The Sojourner’s Sanctuary, your private, secure walk-out basement suite exclusively reserved for solo travelers! Unwind in a supremely comfy queen bed (it has to be experienced to be believed), cook in your full kitchen, focus on work at a dedicated desk, or sip coffee on your private patio, surrounded by nature in a quiet, tree-lined Greenville, SC neighborhood. Whether you’re here for work, a retreat, or to find your escape, your cozy private sanctuary is ready. Solo occupancy only.

Heart of Fountain Inn: 2BR Gem

Experience a comfortable stay in this cute historic 2 bedroom 1 bath mill house located in the heart of Fountain Inn. •Newly renovated with all new furniture and decor. •Enjoy the convenience of downtown's shops and dining just minutes away. This very walkable neighborhood makes exploring a breeze. •This charming, well-appointed home offers a cozy retreat for all; couples, individuals, families, and dogs*. Welcome to a memorable Palmetto State getaway! *Please see pet fee (dogs only,max 2)

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.

Luxury Country Chic

Enjoy all the luxuries of a stylish space, but be in a serene and peaceful location. High end hotel features. Rain shower, full kitchen, even a soda machine to make it special. Excellent location gives you quiet environment, but it’s close to everything. View the farm outside your window while working at adjustable height desk. Enjoy the fire pit & pebble pool. Farm fresh organic teas from the garden, raw milk for your coffee, free range organic chicken eggs make your stay special!

Serene cottage minutes from downtown Greenville

Our cottage is on a beautiful piece of property that makes you feel secluded and peaceful, but is only minutes away from amazing downtown Greenville, as well as quaint downtown Greer. You will have a fully equipped kitchen, wifi, smart tv, iron, ironing board, plush towels, high thread count sheets, choice of foam or feather pillows, and a choice of relaxing inside or outside on the screened porch with a heated throw. For one night stays please send detail request before reserving.

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.

Family & Pet-Friendly Retreat near Bridgeway & DT

Enjoy a private, pet-friendly retreat in a peaceful neighborhood, featuring a fenced yard, cozy fire pit, and relaxing outdoor lounge perfect for unwinding after a long day. Ideally located just minutes from Bridgeway Station, Downtown Greenville, restaurants, shops, and daily essentials. Perfect for couples, small families, remote workers, or weekend escapes, offering comfort, privacy, and convenience in one charming stay designed to make you feel right at home.

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!

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!

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, Happy Place, the swamp rabbit trail, 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.