Holiday houses in Simpsonville

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Top-rated holiday rentals in Simpsonville

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Top Guest favourite
A serene bedroom features a spacious bed dressed in light linens, flanked by a bedside table with a soft lamp. A modern hanging light fixture adds a stylish touch, while a decorative plant and a cozy area rug complete the inviting atmosphere.
Guest suite in Greenville
5 out of 5 average rating, 98 reviews

The Peaceful Retreat Estate in Greenville, SC.

The Peaceful Retreat Estate offers guests a beautifully designed and European modern living experience in Greenville, South Carolina. The five acre property is nestled in a variegated wooded environment with a gentle running stream allowing for a space to truly enjoy healthy living. The superb location provides convenient access to key points of interest and areas in the city. Come and enjoy a place where you can pause--enjoy a simple rest, work with clarity, or refocus on what matters in life.

Top Guest favourite
An open-concept living area features a modern kitchen with stainless steel appliances and a spacious island, complemented by a dining table. A cozy living room is equipped with a soft sectional sofa facing a mounted television and warm electric fireplace. Natural light enhances the inviting atmosphere.
Home in Greenville
4.97 out of 5 average rating, 142 reviews

Greenville GEM Luxurious Retreat in Prime Location

Beautifully renovated 3 beds, 2 baths haven! This gem is a tranquil & stylish retreat, blending modern & cozy charm. Spacious bedrooms, each with plush bedding and storage. Two Bathrooms with soaking tub and a spacious walk-in shower. Cozy living room with a fireplace, TV, and comfy seating.  Fully equipped kitchen, Wi-Fi, Private deck and gazebo, fenced yard. Close to the city's best attractions, dining, and entertainment options. This is the perfect home base for your Greenville adventures.

Guest favourite
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
4.9 out of 5 average rating, 114 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.
Guesthouse in Fountain Inn
4.97 out of 5 average rating, 118 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
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
4.96 out of 5 average rating, 149 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 favourite
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, 110 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 favourite
A split-level home is set amidst a well-maintained lawn, featuring a welcoming entrance with a front door framed by windows. Lush greenery and trees surround the property, and a pathway leads to the entrance, providing easy access.
Home in Greenville
4.99 out of 5 average rating, 185 reviews

2 Living Spaces -2800 ft.²- Sleeps 10

This spacious split-level house is in a quiet neighborhood and has plenty of room for 10 guests. Enjoy a king bed in the master bedroom, and 3 additional bedrooms, each featuring a queen bed. 2 single trundle beds are also available for the little ones. This home has space to gather everyone together or spread out and have some quiet time. Some fun features of this home are an outdoor fire pit, pool table, fenced backyard, deck with grill, and 3 smart TVs. 4 bedroom 3 bath home.

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.
Apartment in Simpsonville
4.99 out of 5 average rating, 328 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 favourite
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, 268 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 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, 139 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
A welcoming living area is displayed, featuring a comfortable sofa and a matching armchair. A wooden coffee table sits in the center, surrounded by a decorative area rug. A flat-screen TV is positioned on a wooden console against the wall, and natural light filters in through nearby windows.
Home in Simpsonville
4.96 out of 5 average rating, 183 reviews

Water Oak Retreat / Comfy king bed, big back yard!

-Private deck with grill and eating area - Fully stocked kitchen with tea, coffee, basic cooking needs and snacks -Safe and quiet neighborhood -1 mile from all of downtown Simpsonville's shops and restaurants -1 mile to huge park with playground, tennis, pickleball, basketball, walking trail, and farmers market -Short 20 minute drive to downtown Greenville -Perfect for families and those traveling for work

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, 109 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.

Popular amenities for Simpsonville holiday rentals

When is the best time to visit Simpsonville?

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Avg. price$155 AUD$145 AUD$145 AUD$164 AUD$148 AUD$162 AUD$161 AUD$155 AUD$161 AUD$158 AUD$155 AUD$162 AUD
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.

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 $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    100 of Simpsonville holiday 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!