Simpsonville vacation rentals

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Top-rated vacation rentals in Simpsonville

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

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Guest favorite

Guesthouse in Fountain Inn

4.92 out of 5 average rating, 263 reviews

Main Street Guest Cottage

The Main Street Cottage is close to downtown Fountain Inn, five excellent restaurants, the county library, Younts performance center, museum, Farmers Market, Swamp Rabbit Trail (hiking, cycling), and I-385 (Greenville in 20 min). You’ll love this separate apartment because of the location, the outdoors space and the small town ambiance. Very good for couples, business travelers, and families (with kids). We are within two blocks of downtown, but the apartment enjoys a quiet residential setting.

Jul 19 – 26

$72 per night

Guest favorite

Cottage in Lyman

4.99 out of 5 average rating, 232 reviews

Lakeside Retreat

With quiet views on Lyman Lake in South Carolina, this cottage is a great place to rest and relax. Close to Greenville and Spartanburg, SC. You’ll love my place because of the location, the ambiance, and the outdoor space. My place is good for couples, solo adventurers, and business travelers. GSP Airport-7 miles, Peace Center/Downtown Greenville-15 miles, Downtown Spartanburg-15 miles, Clemson Univ-42 miles, Furman Univ-14 miles, Tryon- 14 miles, Charlotte Airport-73 miles Asheville-46 mi

Oct 1 – 8

$107 per night

Guest favorite

Apartment in Taylors

4.98 out of 5 average rating, 252 reviews

Indigo Terrace Luxury Bathroom Couples Retreat

Indigo Terrace is a brand 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.

Jul 8 – 15

$88 per night

Guest favorite

Home in Simpsonville

4.97 out of 5 average rating, 187 reviews

Willow Oak Retreat // Comfy beds & Large backyard!

Welcome to Willow Oak Retreat! We cant wait to host you! - Clean and sanitized with care, contactless entry - 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, frisbee golf, tennis, basketball and farmers market. - Short 20 minute drive to downtown Greenville - Perfect for families and those traveling for work!

Jul 15 – 22

$123 per night

Guest favorite

Tiny home in Greenville

4.93 out of 5 average rating, 140 reviews

Tiny house that isn’t tiny but it is beautiful!

This home is located in a extremely quiet, well managed community. Near both Prisma and Bon Secours hospitals. Within 5 minutes of downtown Greenville. 250 square foot dog run. Up to two dogs under 12 pounds and fully house trained allowed. If you love to cook this kitchen is for you. And if you want to grill check out the Big Green Egg Grill. Love to ride or hike - we are very close to Swamp Rabbit Trail and many other nature parks. Bikes can be kept in the laundry building off the deck.

Feb 15 – 22

$77 per night

Superhost

Shipping container in Greenville

4.83 out of 5 average rating, 158 reviews

Container Cottage

Our Container Cottage is a rustic, former shipping container, now cozy cottage. Enjoy Greenville, SC at the only container home conveniently located to downtown Greenville. Sleep easy knowing that the neighborhood is safe. A fire station is located just a block over. The entire interior of the home is crafted with reclaimed wood. A short drive to downtown. Fenced in yard and dog friendly. Just a street over from a busy highway to which we have no control over the sound that carries over.

Sep 21 – 28

$91 per night

Guest favorite

Guesthouse in Greenville

4.99 out of 5 average rating, 356 reviews

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.

Jan 27 – Feb 3

$102 per night

Guest favorite

Farm stay in Fountain Inn

4.94 out of 5 average rating, 137 reviews

The Fountain Moon Cabin on Hidden Pasture Farm

Such a unique property, do not miss this special place. We have so much to offer nature and animal lovers. Quiet and peaceful, The Fountain Moon Cabin at Hidden Pasture Unicorn Farm® is a breathtaking getaway to relax and enjoy nature or some good old fashioned gettin' back to center, your center. We are nestled on small pond with dock, canoe and paddle boat, plus fishing. We have trails and a wonderful agritourism visiting area and are the only visiting Unicorn Farm® in the world.

Oct 4 – 11

$105 per night

Guest favorite

Apartment in Simpsonville

4.99 out of 5 average rating, 243 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.

Jul 8 – 15

$85 per night

Guest favorite

Farm stay in Easley

4.99 out of 5 average rating, 185 reviews

Dogwood Cottage- farm charm - Greenville & Clemson

A retreat in and of itself! This perfect, peaceful cottage is complete with full kitchen, bath and private porch. This converted llama barn elevates reclaimed woods and metals into a darling spot on our 24 acre farm. Serene and tranquil yet only minutes from downtown Greenville or Clemson activities. Nature galore with walking, fishing and even farm animals to meet. Our farm sits at the foot of the Blue Ridge with many quaint mountain towns to visit.

Jul 14 – 21

$91 per night

Guest favorite

Home in Greenville

4.99 out of 5 average rating, 196 reviews

Grateful GVL Gathering

Welcome to Grateful GVL Gathering! Experience all that Greenville has to offer with this newly renovated home that has everything you'll need for your stay. Conveniently located in the Greater Overbrook neighborhood only 1.5 miles from downtown. Whether you're looking to shop and explore, see a show at Bon Secours Arena, enjoy the great outdoors, or attend a Clemson game, this location is perfect for any and all travelers!

Jan 27 – Feb 3

$100 per night

Guest favorite

Apartment in Simpsonville

4.92 out of 5 average rating, 124 reviews

Private Apartment in Great Location

Stay in a tastefully decorated basement apartment with its own entrance close to downtown Simpsonville with eating, shopping, and healthcare within a mile or two. Convenient to I-385 and only 15 minutes from downtown Greenville with all of its amenities. This apartment comes with 2 bedrooms, 1 bath, full kitchen and living room. It can accommodate 2-3 couples (extra sleeper sofa) or a family. Wifi and Smart TV included.

May 6 – 13

$86 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simpsonville vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Simpsonville's top sights

CCNB Amphitheatre at Heritage Park8 locals recommend

Heritage Park9 locals recommend

Regal Simpsonville & IMAX9 locals recommend

Applebee's Grill + Bar5 locals recommend

Papa's and Beer, Simpsonville11 locals recommend

Ice Cream Station19 locals recommend

Other great vacation rentals in Simpsonville

Guest favorite

Farm stay in Greer

4.95 out of 5 average rating, 157 reviews

Farmhouse Getaway

Aug 30 – Sep 6

$107 per night

Guest favorite