Vacation rentals in Simpsonville

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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, 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

Superhost
A renovated 1972 Argosy Airstream is showcased under a spacious wooden shelter. The exterior features a vibrant blue and white color scheme. A large porch is visible, highlighted with soft lighting and set amidst a wooded area, providing a serene outdoor space for relaxation.
Camper/RV in Fountain Inn
4.9 out of 5 average rating, 125 reviews

Creative Oasis in Retro Airstream | wifi, AC, heat

Hola! So happy you found us. Come have your creative getaway in nature in our colorfully renovated 1972 Argosy Airstream. We didn't want you to have to squeeze into a tiny camper bathroom, so we made a brand new concrete/tile bathroom to give you extra space to get ready to explore the town in style. Private Roku tv in bedroom, wifi, coffee setup, books, AC/Heat, huge porch for relaxing. 25 minutes to downtown Greenville, near plenty of hikes and trails, or you can relax in nature at home :)

Top guest favorite
Home in Simpsonville
5 out of 5 average rating, 15 reviews

Safe & Quiet 4/3 Huge Yard | Downtown Simpsonville

Brand new listing, hosted by experienced local Superhosts - this fully renovated 4BR/3BA single-story home is designed with families in mind. Located in a quiet, safe neighborhood less than 1 mi. from downtown Simpsonville, the home features smart TVs in every bedroom, high-speed Wi-Fi, a fully stocked kitchen, kid-friendly amenities, and a large backyard. Comfortable, clean, and stress-free from arrival to checkout. Traveling with a large group? Ask about our house across the street too!

Top guest favorite
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
4.98 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 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 out of 5 average rating, 20 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 favorite
The exterior of a light yellow cottage is visible, framed by lush greenery. A covered entrance leads to the front door, flanked by two windows. Soft sunlight casts gentle shadows, enhancing the natural surroundings. The peaceful setting is complemented by well-maintained shrubs and trees.
Home in Simpsonville
4.91 out of 5 average rating, 102 reviews

Simple Circle Cottage - Quiet. Quaint. Close.

Just 3 blocks from the heart of downtown Simpsonville - come enjoy all that our charming town has to offer without giving up the peace & quiet of a country retreat! Walk to a variety of small retail shoppes and restaurants including Southern-style BBQ, Mexican, Thai, Pizza, authentic crêpes, gourmet coffee, ice cream and more! The police & fire stations are within 1 block, as well as City Park. 3 min to Heritage Park Amphitheater <15 min to downtown Greenville 20 min to GSP AIrport

Top guest favorite
A well-maintained two-story brick home is shown, featuring a charming front porch with seating. Lush greenery surrounds the entrance, and a clean brick pathway leads to the front door. The manicured lawn contributes to the inviting appearance of the property.
Home in Fountain Inn
5 out of 5 average rating, 47 reviews

Heart of Downtown Fountain Inn

Southern hospitality defines Downtown Fountain Inn, SC. This beautiful two story 3 bedroom/2 bath home is located in the heart of historic downtown Fountain Inn, SC. Walk to bars, breweries, and many restaurants in a matter of seconds. 5 minute drive to CCNB amphitheater at Heritage Park, 10 minutes to Downtown Simpsonville and just 25 minutes to Downtown Greenville and the Bon Secours Wellness Arena. Conveniently located 2 miles from Interstate 385 and 20 minutes from GSP Airport.

Guest favorite
A contemporary living area features a comfortable gray sofa with accent pillows, positioned beside a coffee table. A flat-screen TV is mounted on a shiplap wall above an electric fireplace. Natural light floods the space through window coverings, illuminating the stylish decor.
Home in Simpsonville
4.97 out of 5 average rating, 148 reviews

Modern Farmhouse in Downtown Simpsonville, SC

Newly renovated two-bedroom home located in downtown Simpsonville, within easy walking distance of an excellent variety of restaurants, shops and places of interest. A spacious private balcony, leading off from the main bedroom suite overlooks a peaceful backyard... a great place to relax outdoors! The kitchen is fully equipped for preparing great meals. Our home is thoroughly and professionally cleaned & sanitized. ***Please note there is a train that runs midday and late at night.

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, 338 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
4.82 out of 5 average rating, 108 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 favorite
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, 156 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 favorite
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, 195 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

Popular amenities for Simpsonville vacation rentals

When is the best time to visit Simpsonville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,645 GYDG$25,110 GYDG$23,645 GYDG$23,854 GYDG$21,553 GYDG$23,645 GYDG$23,436 GYDG$22,599 GYDG$23,436 GYDG$23,017 GYDG$22,599 GYDG$23,645 GYD
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 vacation rentals in Simpsonville

  • Total vacation rentals

    Explore 100 vacation rentals in Simpsonville

  • Nightly prices starting at

    Simpsonville vacation rentals start at G$6,277 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,820 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 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

    60 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!