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Holiday rentals in Simpsonville

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Quick stats about holiday rentals in Simpsonville

  • Total holiday rentals

    Explore 100 holiday rentals in Simpsonville

  • Nightly prices starting at

    Simpsonville holiday rentals start at £23 per night before taxes and fees

  • Verified guest reviews

    Over 3,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    90 of Simpsonville holiday rentals include wifi 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 holiday rentals in Simpsonville

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

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Guest favourite
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, 117 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

Top guest favourite
A screened porch is highlighted, featuring comfortable wooden seating with light cushions and a matching table. Natural light is allowed through large windows and a skylight, providing a view of the surrounding greenery. A small potted plant decorates the table, enhancing the relaxing atmosphere.
Home in Greenville
4.96 out of 5 average rating, 157 reviews

The Greenville Nest - Retreat & Relaxation Home

This beautifully one-level home offers 3 queen beds and 2 baths, accommodating up to 6 guests. Centrally located in a peaceful neighborhood. 8-minute drive to GSP airport, 15-minute drive to downtown Greenville, minutes from I-85/385, and minutes from Woodruff and Pelham Rd. You'll appreciate the easy access to food delivery and restaurants. Enjoy a stylish Experience for entertaining, working, and relaxing with high-speed Wi-Fi. Quiet and safe with an enjoyable private screened porch and Grill.

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
4.89 out of 5 average rating, 125 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>

Top guest favourite
The spacious living area features a comfortable gray sofa with decorative pillows, a small dining table, and modern kitchen appliances. Natural light fills the room through sliding glass doors that open to a view of the outdoors. A light-colored area rug adds warmth to the space.
Guest house in Fountain Inn
4.98 out of 5 average rating, 128 reviews

Upscale cottage in Downtown Fountain Inn

All new cottage/studio apartment. 5 minutes to CCNB amphitheater at Heritage Park, 10 minutes to downtown Simpsonville, 25 minutes to Bon Secours Wellness Arena in downtown Greenville. 20 minutes from GSP airport. Close to Hillcrest Hospital and Bon Secours in Simpsonville. 25 minutes from Presbyterian College, 30 minutes from Furman University. Guest have access to partially fenced backyard as well as full access to private cottage. Host lives on property! There is NO Bathroom Door.

Top guest favourite
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.
Flat in Simpsonville
5 out of 5 average rating, 22 reviews

Luxury Country Chic

Enjoy all the luxuries of a stylish space, but be in a serene and peaceful location. High end hotel features. Rain shower, full kitchen, even a soda machine to make it special. Excellent location gives you quiet environment, but it’s close to everything. View the farm outside your window while working at adjustable height desk. Enjoy the fire pit & pebble pool. Farm fresh organic teas from the garden, raw milk for your coffee, free range organic chicken eggs make your stay special!

Guest favourite
A charming home with a dark blue exterior is surrounded by a grassy yard and mature trees. A white picket fence encircles the property in the background. The welcoming front porch is adorned with a decorative wreath, inviting guests to enter this comfortable space.
Home in Five Forks
4.9 out of 5 average rating, 250 reviews

Peaceful Oasis Convenient to Greenville!

Fully updated and upgraded in June 2021, this open floor plan 3bedroom / 2 full bathroom home-away-from-home is perfect for a family or professional traveling for work. We have WiFi TV, and WFi internet, . We have put careful thought into each room and it's our goal to make it comfortable and enjoyable for your stay! We are located between Greenville & Simpsonville in an area known as "Five Forks" - convenient to Woodruff Rd that has everything you need from shopping to restaurants.

Top guest favourite
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.
Flat in Simpsonville
4.99 out of 5 average rating, 339 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.

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, 109 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!

Top guest favourite
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, 265 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!

Top guest favourite
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, 157 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 favourite
The living area is enhanced by warm wooden walls and features large windows allowing natural light. A blue sofa is paired with an orange chair, accented by cushions. A rustic coffee table sits on a patterned rug, while a small kitchen area is visible in the background.
Cabin in Simpsonville
5 out of 5 average rating, 124 reviews

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.

Superhost
Home in Simpsonville
4.67 out of 5 average rating, 6 reviews

Preserved Charm & Comfort | Downtown Simpsonville

Stay in the heart of Downtown Simpsonville, just two blocks from the action. This beautifully restored home blends antique charm with modern comfort, inspired by the Woodside Mill era of the 1930s. Walk to live music, outdoor dining, shops, and pickleball courts, then unwind in a fresh, welcoming space. You’re also just 20 minutes to Downtown Greenville and 15 minutes to GSP Airport.

Popular amenities for Simpsonville holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Simpsonville's top sights

Papas And Beer

13 locals recommend

Heritage Park

20 locals recommend

CCNB Amphitheatre at Heritage Park

23 locals recommend

Other great holiday rentals in Simpsonville

Top guest favourite
The outdoor area features a saltwater pool reflecting the evening sky, surrounded by comfortable lounge chairs and umbrellas. The two-story home showcases large windows, allowing warm light to illuminate the interior spaces. A hot tub is positioned nearby, enhancing the inviting atmosphere.
Home in Simpsonville
4.96 out of 5 average rating, 46 reviews

The Wright Place! 25/min DT G-Ville. Pool/Hottub.

Guest favourite
Home in Simpsonville
5 out of 5 average rating, 23 reviews

Downtown Simpsonville/5 Private Bedrooms/Pergola

Top guest favourite
An outdoor seating area is arranged around a circular fire pit, surrounded by gravel and plants. String lights hang above, creating a warm ambiance. The tiny house features a covered porch with steps leading down. Large windows offer glimpses of the interior.
Tiny home in Greenville
4.97 out of 5 average rating, 65 reviews

Tiny Home, Hot Tub, Pet Allowed, Fire Pit, Oasis!

Top guest favourite
Home in Fountain Inn
4.93 out of 5 average rating, 95 reviews

3BR Home w Fire Pit, Grill & Private Backyard

Guest favourite
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, 87 reviews

Peaceful Retreat with Spacious Backyard & Fire Pit

Top guest favourite
Home in Mauldin
5 out of 5 average rating, 56 reviews

Fire Pit Retreat | Pet Friendly | Near Greenville

Guest favourite
A well-appointed bedroom features a spacious bed draped in neutral linens, complemented by accent pillows. A pull-out twin bed is positioned underneath. Natural light fills the room through a large window dressed with sheer curtains, while a dresser and decorative lamp add functional elegance.
Home in Simpsonville
5 out of 5 average rating, 31 reviews

Southern Charm Townhome

Top guest favourite
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, 68 reviews

Fountain Inn on Main St

When is the best time to visit Simpsonville?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price£85£90£85£86£78£85£84£81£84£83£81£85
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