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 :)

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!

The Cottage at Old Oaks Farm

Built in the early 1900's, this serene cottage is located approximately one mile from Furman University at the base of Paris Mt. It has been lovingly improved, but the floors are a bit slanted and no corner is exactly square. Located in a neighborhood on a five acre farm, it consists of three large rooms, comfortably furnished and lots of natural light. The cottage is convenient to downtown Greenville(5 miles),Travelers Rest, Furman, and the Swamp Rabbit Trail. No pet fee or cleaning fee.

Indigo Terrace Luxury Bathroom Couples Retreat

Indigo Terrace is a new one-bedroom basement apartment perfect for a couple, small family or business traveler. This modern space features a beautiful, spacious bathroom (with tub for 2!), full kitchen, one bedroom with queen bed, and sleeper sofa in living room. It’s located in a quiet, tree-lined neighborhood and has a private driveway & entrance with self check-in. Conveniently situated off a main road, it's close to GSP airport, Taylors Mill, and just 8 miles from downtown Greenville.

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.

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/convenient apartment in Simpsonville (A)

Welcome to our beautiful home-away-from-home in the heart of Simpsonville! This bright and modern private studio features a kitchenette, queen bed, smart TV, high-speed Wi-Fi, and a cozy workspace. Steps from cafes, restaurants, and Prisma Health Hillcrest Hospital, perfect for a travel nurse. You’ll love exploring the city on foot. Perfect for solo travelers or couples. NOTE: For long stays (more than 2 weeks) count with a W/D you’ll share.

Walk Downtown Simpsonville 3/1

Walk to Downtown Simpsonville Main Street only a few blocks away. This refinished 3BR/1BA is ready for our first guests. New kitchen with new SS appliances and W/D, new paint throughtout and new bathroom vanity/floor, refinished hardwood floors throughout. Quiet residential neighborhood. Walk to Eggs Up Grill for a great breakfast, and continue another block to restaurants, ice cream, coffee shops, etc. Be our first guests!

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.

Downtown Simpsonville Cozy Cabin

Come stay at our "Cozy Cabin" just 2 short blocks from everything Downtown Simpsonville has to offer! This cozy, well-appointed cabin has everything you need for an enjoyable stay in the heart of Simpsonville. Enjoy live music, outdoor dining and more just steps away from this cozy retreat. The home is just 20 minutes from Downtown Greenville and 25 minutes from GSP International Airport.