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.

Guest favorite

Guesthouse in Fountain Inn

4.92 out of 5 average rating, 257 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 4 – 11

$72 per night
Guest favorite

Home in Greenville

4.97 out of 5 average rating, 148 reviews

A Tranquil Place (near downtown Greenville)

A Tranquil Space is conveniently located close to Downtown Greenville. The large suite includes the bedroom, living area, kitchenette (fridge/freezer/convection oven), bathroom, and study/eating area. It is newly renovated area on the end of my home with a private entrance. The space is welcoming and inviting...a perfect space to get away from the hustle. Although minutes from Downtown, the suite feels like you're in the mountains with a private back yard and many trees. Enjoy your stay!

Aug 3 – 10

$87 per night
Guest favorite

Home in Simpsonville

4.97 out of 5 average rating, 185 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!

Sep 15 – 22

$146 per night

Popular amenities for Simpsonville vacation rentals

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

Tiny home in Greer

4.93 out of 5 average rating, 121 reviews

Shalom Tiny with Lake View - Greer, SC

Nov 21 – 28

$100 per night
Guest favorite

Home in Greenville

4.99 out of 5 average rating, 126 reviews

2 Living Spaces -2800 ft.²- Sleeps 10

Feb 13 – 20

$188 per night
Guest favorite

Guesthouse in Fountain Inn

4.85 out of 5 average rating, 84 reviews

The Woodlands - Spacious Apt in Central Location!

Jul 18 – 25

$66 per night
Guest favorite

Home in Simpsonville

4.98 out of 5 average rating, 48 reviews

Cozy Rural Home on a Family Farm

Aug 11 – 18

$65 per night
Guest favorite

Guesthouse in Fountain Inn

5.0 out of 5 average rating, 53 reviews

Upscale cottage in Downtown Fountain Inn

Jun 1 – 8

$99 per night
Guest favorite

Guesthouse in Mauldin

4.92 out of 5 average rating, 52 reviews

TICA’S HOME Your cozy Home away from Home

Feb 13 – 20

$81 per night
Guest favorite

Home in Simpsonville

4.96 out of 5 average rating, 81 reviews

Cheery southern cottage

Sep 18 – 25

$142 per night
Guest favorite

Home in Simpsonville

5.0 out of 5 average rating, 16 reviews

House Frieda

Dec 21 – 28

$144 per night
Guest favorite

Home in Fountain Inn

5.0 out of 5 average rating, 5 reviews

Fully Furnished Cozy 1 bd home

Feb 19 – 26

$65 per night
Guest favorite

Cabin in Simpsonville

5.0 out of 5 average rating, 28 reviews

Downtown Simpsonville Cozy Cabin

Jun 10 – 17

$132 per night
Guest favorite

Home in Simpsonville

5.0 out of 5 average rating, 22 reviews

"Red Barn Retreat"

Oct 14 – 21

$134 per night
Guest favorite

Guesthouse in Greenville

4.98 out of 5 average rating, 64 reviews

Finished Room over Garage (FROG) on Reedy River

Apr 8 – 15

$65 per night

Other great vacation rentals in Simpsonville

Guest favorite

Home in Simpsonville

4.96 out of 5 average rating, 24 reviews

Charming Simpsonville 3BR/2BA Home, Pet-Friendly!

Apr 24 – May 1

$93 per night
Guest favorite

Cottage in Greer

4.98 out of 5 average rating, 53 reviews

Serene cottage minutes from downtown Greenville

Jan 19 – 26

$100 per night
Guest favorite

Home in Simpsonville

4.94 out of 5 average rating, 18 reviews

Yellow Door Cottage Home

Jan 23 – 30

$104 per night
Guest favorite

Home in Gray Court

5.0 out of 5 average rating, 24 reviews

Little slice of heaven

Apr 15 – 22

$114 per night
Superhost

Apartment in Greenville

4.94 out of 5 average rating, 33 reviews

Entire 2 bedrooms 1 Bath Apartment in Greenville

Aug 22 – 29

$69 per night
Guest favorite

Guesthouse in Simpsonville

4.99 out of 5 average rating, 73 reviews

The Loft at Helen

Nov 5 – 12

$89 per night
Guest favorite

Home in Simpsonville

5.0 out of 5 average rating, 31 reviews

Cheerful 2-bedroom residential home

Mar 17 – 24

$115 per night
Guest favorite

Home in Fountain Inn

4.84 out of 5 average rating, 63 reviews

Walk to Downtown from Cheerful 3BR Private Home

Sep 28 – Oct 5

$94 per night
Guest favorite

Guest suite in Greenville

4.99 out of 5 average rating, 88 reviews

Private Guest House 4.5 Miles from GSP Airport

Jun 22 – 29

$113 per night
Guest favorite

Guesthouse in Greenville

4.97 out of 5 average rating, 33 reviews

Adorable Tiny guest house for 1

Nov 6 – 13

$55 per night
Guest favorite

Guest suite in Simpsonville

4.97 out of 5 average rating, 77 reviews

Godfrey Suite is upstairs in Century Old Farmhouse

Jun 28 – Jul 5

$80 per night
Guest favorite

Home in Greenville

4.89 out of 5 average rating, 85 reviews

Comfortable 3 Bedroom w/ Wi-Fi

Aug 13 – 20

$106 per night

Quick stats about vacation rentals in Simpsonville

Total rentals

50 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.9K reviews

Nightly prices starting at

$30 before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Simpsonville?

    Four-legged friends are welcome in Simpsonville. Choose from more than 10 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 20 vacation rentals in Simpsonville featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Simpsonville have air conditioning?

    Absolutely! We offer over 30 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 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Simpsonville have wireless internet?

    Absolutely! We offer over 30 house rentals with wireless internet in Simpsonville. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore