Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A renovated 1972 Argosy Airstream is showcased under a spacious wooden shelter. The exterior features a vibrant blue and white color scheme. A large porch is visible, highlighted with soft lighting and set amidst a wooded area, providing a serene outdoor space for relaxation.
Camper/RV in Fountain Inn
4.91 out of 5 average rating, 114 reviews

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 :)

Top guest favorite
The studio features a spacious bed with a light-colored coverlet, accompanied by a decorative pillow. Two chairs are positioned beside a small table, and a kitchenette with a refrigerator, microwave, and coffee maker is visible in the corner. Natural light enters through the door leading to the outside.
Guest suite in Simpsonville
4.97 out of 5 average rating, 131 reviews

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).

Top guest favorite
A charming house is set amidst a well-maintained yard, surrounded by green shrubs and trees. The front porch features white chairs and decorative elements, while the gray roof and light-colored siding present a welcoming appearance. Natural light bathes the area, enhancing its tranquil feel.
Guest suite in Simpsonville
4.98 out of 5 average rating, 105 reviews

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.

Top guest favorite
A serene porch area welcomes visitors with hanging ferns and vibrant pink roses bordering the space. A wooden swing and two chairs provide comfortable seating options, while the entrance features a wooden door framed by a decorative piece. Soft natural light creates a tranquil atmosphere.
Apartment in Simpsonville
4.99 out of 5 average rating, 315 reviews

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.

Top guest favorite
A cozy campsite is illuminated by string lights in the evening. A vintage camper is situated under a wooden canopy, with a stone path leading to a fire pit surrounded by two wooden chairs. Nearby, a small table provides an additional seating area.
Camper/RV in Woodruff
4.98 out of 5 average rating, 146 reviews

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.

Guest favorite
A cozy living space features rich wooden floors and a white brick fireplace as a focal point. Comfortable seating is arranged in front of the fireplace, with soft natural light filtering through the large windows. The adjoining kitchen is visible, showcasing wooden cabinetry.
Home in Simpsonville
4.97 out of 5 average rating, 245 reviews

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, basketball and farmers market. - Short 20 minute drive to downtown Greenville - Perfect for families and those traveling for work!

Top guest favorite
The open living area features a striped armchair facing a wooden coffee table. A kitchen with white cabinetry and a breakfast bar is seen in the background, equipped with modern appliances and natural lighting from multiple windows.
Guesthouse in Simpsonville
4.95 out of 5 average rating, 259 reviews

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.

Top guest favorite
A cozy sleeping area features a full bed adorned with a quilted coverlet in red, white, and blue. Decorative elements include wall art in circular frames and a vintage windmill accent. Soft lighting from bedside lamps enhances the space's warmth.
Tiny home in Fountain Inn
4.99 out of 5 average rating, 121 reviews

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!

Top guest favorite
A charming cottage is set among lush greenery, featuring a spacious deck that extends from the front. Large windows provide natural light, while surrounding trees and plants create a serene atmosphere.
Guesthouse in Greenville
5 out of 5 average rating, 155 reviews

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.

Top guest favorite
A cozy living area features a brown sofa adorned with decorative pillows, flanked by large windows allowing natural light to fill the space. A private outdoor seating area includes a shaded daybed surrounded by greenery, providing a peaceful retreat.
Guesthouse in Mauldin
4.9 out of 5 average rating, 231 reviews

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!

Top guest favorite
A cozy living area features a brown leather sofa adorned with cushions in neutral and mustard tones. A decorative vase with tall pampas grass is positioned on a wooden coffee table. A wall art piece depicting a dog adds character to the space.
Tiny home in Greenville
4.98 out of 5 average rating, 116 reviews

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.

Superhost
A cozy entrance area features a doorway with an oval window, complemented by a small wooden table with a decorative plant. A media console is positioned against the wall, while a brown couch is visible, inviting relaxation. Warm tones create a comforting ambiance.
Apartment in Simpsonville
4.71 out of 5 average rating, 444 reviews

Cozy studio apartment near downtown Simpsonville.

This cute and cozy studio apartment is attached to my house with a private entrance. It is fully furnished with plenty of amenities. Come check it out!! It is just minutes from 385 and lots of restaurants and shopping. *** It is also only 6 min. (2.5 miles) from CCNB amphitheater at Heritage park! ***

Popular amenities for Simpsonville vacation rentals

When is the best time to visit Simpsonville?

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Avg. priceG$22,591 GYDG$21,126 GYDG$21,126 GYDG$23,846 GYDG$21,545 GYDG$23,636 GYDG$22,800 GYDG$23,218 GYDG$24,055 GYDG$26,565 GYDG$22,591 GYDG$23,846 GYD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Simpsonville?

    Four-legged friends are welcome in Simpsonville. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Simpsonville?

    Yes! Work meets play with ease at over 60 vacation rentals in Simpsonville featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Simpsonville vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Simpsonville, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Simpsonville have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Simpsonville. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Simpsonville have air conditioning?

    Absolutely! We offer over 70 house rentals with air conditioning in Simpsonville. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Simpsonville?

    Experience the best of Simpsonville with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Simpsonville?

    Simpsonville has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Simpsonville have wifi?

    Absolutely! We offer over 70 house rentals with wifi in Simpsonville. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Simpsonville

  • Total vacation rentals

    Explore 100 vacation rentals in Simpsonville

  • Nightly prices starting at

    Simpsonville vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,330 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Simpsonville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Simpsonville rentals

  • 4.8 Average rating

    Simpsonville stays are highly rated by guests—averaging 4.8 out of 5!