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Vacation rentals in Simpsonville

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Quick stats about vacation rentals in Simpsonville

  • Total vacation rentals

    Explore 90 vacation rentals in Simpsonville

  • Nightly prices starting at

    Simpsonville vacation rentals start at R 478 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 4,020 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 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

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 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!

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 serene bedroom features a spacious bed dressed in white linens, complemented by decorative pillows. Two bedside tables with lamps frame the bed, while a television is mounted on the wall across from it. Natural light filters through sheer curtains, enhancing the calming atmosphere.
Home in Simpsonville
4.93 out of 5 average rating, 121 reviews

Hidden Gem - Private Home - 3 BDRM In 5 Forks

Freshly renovated 3 bedroom home in highly sought after 5 Forks area. Beautiful space for family or multiple couples to enjoy inside or outside with open living and big back deck. Stay in and cook in our gorgeous kitchen that any woman would want to bring home with them OR go out and have many options at your fingertips on Woodruff Road. Come back to our comfortable queen sized beds in each bedroom and enjoy the peace and quiet of our home and 1.5 acre lot. Pet fee is required for furry friend

ValueFamilyGrill

Guest favorite
The outdoor area showcases a tranquil pool surrounded by lush greenery, with comfortable lounge chairs positioned nearby. A pastel sunset provides a serene backdrop, while inflatable pool accessories add a playful touch to the inviting atmosphere.
Home in Simpsonville
4.93 out of 5 average rating, 106 reviews

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!

ValueLocationKitchen

Superhost
A bright living room features a comfortable gray sofa, patterned accent chairs, and a glass coffee table. Large windows allow natural light to fill the space. In the outdoor area, a playground with a slide and climbing structure is visible within a fenced yard, perfect for children.
Home in Simpsonville
4.88 out of 5 average rating, 131 reviews

Spacious 4 BR Escape w/ Fenced Yard Near Downtown

Welcome to your stylish retreat, conveniently located just 3 minutes from the shopping & dining in charming Downtown Simpsonville & convenient to everything that Greenville has to offer. With 4 bedrooms, 2 full baths & a fenced in yard, this house has everything you need for your stay. Located in a safe & quiet neighborhood just 20 minutes from downtown Greenville & 5 minutes to all of your daily needs. <B>Traveling with a large group? Ask about our other 4BR house across the street!<B>

ValueLocationBathroom

Superhost
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 Five Forks
4.96 out of 5 average rating, 168 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/stay. It’s fenced and locked at all times. Signed liability waiver required).

FamilyLocationHospitality

Guest favorite
A single-story home is presented with a welcoming façade, featuring beige siding and dark shutters. The landscaped front yard is adorned with vibrant flowers and greenery, enhancing the natural surroundings. A wooden deck with steps leads to the entrance, framed by a manicured lawn.
Home in Simpsonville
4.92 out of 5 average rating, 91 reviews

Peaceful Retreat with Spacious Backyard & Fire Pit

Welcome to House Frieda in the heart of downtown Simpsonville. This private, beautifully maintained home offers the perfect balance of comfort and convenience, nestled in a peaceful, nature-surrounded neighborhood. Enjoy a spacious backyard with a new fire pit for relaxing evenings. Equipped with enhanced amenities beyond the typical Airbnb, this home is ideal for families, extended stays, or business travelers. Advanced AC with UV sterilization keeps indoor air clean and fresh.

ValueFamilyDecor

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, 345 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.

ValueFamilyWalkability

Top guest favorite
The exterior of the residence is shown, highlighting a welcoming front porch adorned with a green accent. Lush shrubs frame the entrance, complemented by a well-kept lawn. A blacktop driveway leads to a private gate and additional outdoor space visible beyond.
Home in Fountain Inn
4.97 out of 5 average rating, 71 reviews

Fountain Inn on Main St

Located on Main Street in the heart of Fountain Inn, SC. This private residence features a complete living area, master suite with two additional bedrooms, 2.5 bathrooms. Dining area will accommodate six and the full kitchen has four counter seats. Fire pit, grill, and basketball hoop await you in the backyard with ample parking. Full washer, dryer and a convenient dog door to backyard! Walking distance to The Slice, coffee and ice cream on Main Street. 2 miles from I-385.

LocationFamilyGetting around

Top guest favorite
Home in Simpsonville
5.0 out of 5 average rating, 32 reviews

Comfy, Dog-Friendly, Nice Community

Need good rest on a comfy mattress with soft cotton sheets? Need to be less than 5 minutes away from a grocery store, urgent care and some shops and restaurants? Fenced-in yard?! Then book our place! :) Relax and recharge in our recently refreshed and stylish house with a fenced in yard and patio. Enjoy your nights at a fire-pit making s’mores and grilling dinner on a charcoal grill. Comfortable beds with cotton linens and fluffy down comforters assure a restful sleep!

LocationFamilyView

Superhost
The exterior of the home is shown, featuring a covered front porch with seating and well-maintained landscaping. Surrounding trees provide shade, and the spacious lawn offers an inviting atmosphere. The house is painted in light colors with distinctive window shutters, enhancing its welcoming appearance.
Home in Simpsonville
4.83 out of 5 average rating, 116 reviews

Historic 3BR with Porch near Downtown

Welcome to The Southern Stoop – a newly refreshed, pet-friendly 3-bedroom, 1-bathroom home just a minute from Downtown Simpsonville and 20 minutes to Downtown Greenville. Enjoy a spacious lot with a screened-in porch and classic front stoop. Inside, find updated living spaces, a fully equipped kitchen, and comfortable bedrooms. Perfectly situated near local dining, shopping, and parks, it's your ideal base for a Southern getaway. We can't wait to host you!

ValueLocationHospitality

Top 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, 268 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, pickleball, walking trail, basketball and farmers market. - Short 20 minute drive to downtown Greenville - Perfect for families and those traveling for work!

ValueFamilyCondition

Guest favorite
Home in Mauldin
4.86 out of 5 average rating, 28 reviews

The Haven 15 miles to Downtown Greenville

Four bedrooms upstairs — one king, four queens — plus a queen sofa bed downstairs. 2.5 baths keep mornings simple. • Full kitchen • Office for remote work • Games for rainy days • Free, fast WiFi Relax on the screened patio or gather around the fire pit for s’mores. Big backyard for kids, dogs, and grown-ups to unwind. Long driveway parking. 1 pet welcome per stay. Perfect for exploring Greenville or lazy stay-in days. Book The Haven today!

LocationFamilyBackyard

Top guest favorite
Home in Mauldin
4.97 out of 5 average rating, 69 reviews

3BR | Family & Pet Friendly•Fenced Yard •BridgeWay

Private, pet-friendly Southern-style home minutes from Downtown Greenville! Sleeps up to 6 guests, with the option to add a private guest house for up to 10 guests total. Enjoy a fully fenced backyard with a gazebo, BBQ grill, wood-fired pizza oven, and fire pit, plus smart self check-in, a fully equipped kitchen, TVs in every bedroom, and easy access to BridgeWay Station, shopping, dining, and Greenville’s top attractions.

FamilyValueHospitality

Popular amenities for Simpsonville vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Simpsonville's top sights

Discovery Island

23 locals recommend

CCNB Amphitheatre at Heritage Park

23 locals recommend

Heritage Park

20 locals recommend

Papas And Beer

13 locals recommend

Southside Park

8 locals recommend

Sweet Sippin

5 locals recommend

Other great vacation rentals in Simpsonville

Superhost
Home in Simpsonville
5.0 out of 5 average rating, 28 reviews

Downtown Simpsonville/5 Private Bedrooms/Pergola

ValueFamilyGetting around

Superhost
The exterior of a modern two-unit duplex features a clean white facade with black trim. The entrance is framed by a small porch and a well-defined pathway. Large windows enhance the inviting appearance, while neatly landscaped areas add a touch of greenery.
Home in Simpsonville
5.0 out of 5 average rating, 18 reviews

Entire Duplex with Backyard Firepit | Sleeps 12

FamilyLocationLaundry

Guest favorite
Home in Fountain Inn
4.96 out of 5 average rating, 75 reviews

Heart of Fountain Inn: 2BR Gem

LocationFamilyWalkability

Top guest favorite
A modern dining area features a dark wood table set for four, with decorative plates arranged neatly. The light, airy space is enhanced by an area rug beneath the table, and a potted plant adds a touch of greenery. A kitchen and living area are visible in the background.
Townhouse in Simpsonville
4.94 out of 5 average rating, 31 reviews

Fresh & Charming Townhome

LocationFamilyNearby

Guest favorite
The bedroom features a spacious bed with crisp white pillows and a dark gray blanket. Natural light floods the room through multiple windows, creating a bright atmosphere. A sleek bench and contemporary nightstands complement the minimalist design.
Home in Five Forks
4.97 out of 5 average rating, 76 reviews

Beautiful home in the heart of Five Forks!

LocationFamilyCondition

Top guest favorite
An open-concept living area features modern kitchen cabinetry and stainless steel appliances. A dining table with four chairs is positioned nearby, while a comfortable blue sofa invites relaxation. Large windows provide natural light and views of the surrounding greenery.
Apartment in Simpsonville
5.0 out of 5 average rating, 25 reviews

Luxury Country Chic

LocationFamilyGetting around

Superhost
Home in Simpsonville
5.0 out of 5 average rating, 5 reviews

The Curtis House

FamilyLocationKitchen

Guest favorite
The exterior of a single-story house is shown, featuring a light-colored façade and multiple windows. A shaded front yard includes sparse grass, with trees partially framing the view. The building is situated within a quiet residential area, conveying a sense of peacefulness.
Home in Simpsonville
4.84 out of 5 average rating, 64 reviews

Walk Downtown Simpsonville 3/1

FamilyValueAccuracy

When is the best time to visit Simpsonville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 1,802 ZARR 1,914 ZARR 1,802 ZARR 1,962 ZARR 2,073 ZARR 2,057 ZARR 1,786 ZARR 1,722 ZARR 1,786 ZARR 1,754 ZARR 1,722 ZARR 1,802 ZAR
Avg. temp6°C8°C12°C16°C20°C25°C27°C26°C23°C17°C11°C7°C

Frequently Asked Questions

  • What are the best places to stay in Simpsonville?

    Many guests choose to stay near Simpsonville’s downtown for easy access to dining and events, or around quieter residential neighborhoods near parks. These areas have a range of vacation rentals suited for solo travelers, families, and groups.

  • What are the best things to do in Simpsonville with kids?

    Kids frequently enjoy playgrounds and open spaces at Heritage Park, interactive activities at local recreation centers, and seasonal splash pads. The area also has family-friendly bowling and mini-golf venues.

  • What are some of the best things to do in Simpsonville?

    Explore Heritage Park’s walking trails, catch live music at the amphitheatre, and browse shops or cafés in the downtown area. Community markets and seasonal festivals often create a lively local atmosphere.

  • How is the weather in Simpsonville?

    Simpsonville experiences cool to mild winters around 32–55°F (0–13°C), and warm, humid summers that reach 87–90°F (31–32°C). Rain is fairly consistent year-round, with the most rainfall in summer and winter months.

  • When is the best time to visit Simpsonville?

    Late spring through early fall is often recommended for a visit to Simpsonville, as warm weather and community events are common. Spring brings blooming trees and festivals, while autumn has comfortable temperatures for outdoor activities.

  • What are the best places to visit in Simpsonville?

    Frequently suggested spots in Simpsonville include Heritage Park for outdoor activities, the downtown area for local dining and shops, and nearby cultural centers hosting performances or exhibits. Parks around the city provide open spaces for relaxation.

  • What are some hiking trails in Simpsonville?

    Simpsonville has paved walking and biking trails in Heritage Park and other city greenways. For a longer route, explore trails that pass through forested areas and wetlands, where birdwatching and quiet observation are often enjoyed.

  • What are some family activities we can do in Simpsonville?

    Families frequently enjoy exploring Heritage Park’s playgrounds, attending community festivals, and discovering interactive exhibits at local museums. The city also has bowling lanes and seasonal splash pads, making it easy for all ages to have fun.

  • What are some of the best day trip ideas from Simpsonville?

    Guests often plan day trips to nearby waterfalls, mountain hikes, or historic towns with local shops and markets. Nature reserves and regional museums around the area provide engaging options for different interests.

  • Are there any pet friendly accommodations available in Simpsonville?

    Pet-friendly accommodations are available in Simpsonville, especially in areas near city parks and residential neighborhoods. Many hosts welcome dogs and cats, but it is a good idea to check house rules for specific details.

  • What are some local tips for visiting Simpsonville?

    Locals often suggest visiting on weekends when farmers markets and pop-up events are more common. Early mornings at city parks provide a peaceful experience, and tasting local Southern cuisine is frequently recommended.

  • What is Simpsonville known for?

    Simpsonville is known for its welcoming small-town spirit, local music events, and green spaces such as Heritage Park. The city has a blend of community traditions and easy access to regional attractions.

  • What are the best hidden gems to explore in Simpsonville?

    Exploring Simpsonville’s downtown reveals locally owned shops, public art installations, and quiet parks. Around the city, small museums and nature trails provide opportunities for discovery away from busier spots.

  • What are the best foods to try in Simpsonville?

    Southern classics such as pulled pork barbecue, fried chicken, and pimento cheese are frequently suggested in Simpsonville. Locally owned cafés and bakeries also highlight regional desserts, including cobblers and seasonal pies.

  • What should I bring for a trip to Simpsonville?

    Pack comfortable walking shoes for exploring parks or downtown, and consider layers, as temperatures range widely through the year, from 32°F to 90°F (0°C to 32°C). An umbrella or light rain jacket can come in handy, especially during spring and summer months when rainfall is higher.

  • What is the nightlife in Simpsonville like?

    Simpsonville has a relaxed nightlife scene with local pubs, casual bars, and live music venues concentrated downtown and near main streets. It is common to find venues featuring regional bands and welcoming spaces for conversation.

  • What are the most popular events or festivals in Simpsonville?

    Simpsonville is known for community gatherings at the Heritage Park Amphitheatre, where concerts and regional festivals take place, especially during spring and summer. Seasonal events often bring together music, food, and local crafts for a welcoming atmosphere.

  • Are there family friendly vacation rentals in Simpsonville?

    Simpsonville has many vacation rentals welcoming families, often with features like full kitchens, multiple bedrooms, and outdoor spaces. Neighborhoods around parks and quiet residential areas are frequently suggested for families seeking a comfortable stay.

Destinations to explore