Holiday rentals in Simpsonville

4.98 out of 5 average rating, 45 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!

Guest house in Fountain Inn

4.97 out of 5 average rating, 102 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.

4.96 out of 5 average rating, 138 reviews

Simpsonville Southern Comfort

Welcome to Simpsonville Southern Comfort! Our home offers a comfortable, completely remodeled space with all of the amenities of home to make your stay enjoyable. This home is in a GREAT location just a 5-minute drive from the conveniences of the Five Forks area, and a short 7-minute drive to the enjoyment of The Square in Downtown Simpsonville. Our home is also a quick 20-minute drive from GSP International Airport, and 20 minutes from Downtown Greenville. Enjoy your stay!

4.99 out of 5 average rating, 299 reviews

Flat in Simpsonville

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.

4.98 out of 5 average rating, 126 reviews

Home in Greenville

Family & Pet Friendly Home - Sleeps 8

Our home is absolutely perfect for entertaining, work and relaxation. Enjoy fast wifi and free coffee. Connect over a meal at our spacious dining table. Families will love the large, fenced-in backyard, toys and board games in our huge rec room, complete with ping pong table! Quiet and easy connections to Greenville & Simpsonville. Only 5 mins from Discovery Island Waterpark. Community park and playground accessible with lots of space to roam with family or pets.

Superhost

Bungalow in Simpsonville

4.76 out of 5 average rating, 187 reviews

Yellow Door

Our family enjoyed many happy years in this home and we hope you love it as much as we do! Located in a fully walkable neighborhood- all of your shopping and dining in downtown is a short stroll away. Come and relax on the porch and enjoy the Southern weather. Our beds are plush and our seating areas are perfect for kicking back with friends and family. If you love to cook, we have a fully stocked kitchen for your convenience. Come and see for yourself!

4.98 out of 5 average rating, 43 reviews

Flat in Simpsonville

Private/convenient apartment in Simpsonville (A)

Welcome to our beautiful home-away-from-home in the heart of Simpsonville! This bright and modern private studio features a kitchenette, queen bed, smart TV, high-speed Wi-Fi, and a cozy workspace. Steps from cafes, restaurants, and Prisma Health Hillcrest Hospital, perfect for a travel nurse. You’ll love exploring the city on foot. Perfect for solo travelers or couples. NOTE: For long stays (more than 2 weeks) count with a W/D you’ll share.

4.96 out of 5 average rating, 23 reviews

Walk Downtown Simpsonville 3/1

Walk to Downtown Simpsonville Main Street only a few blocks away. This refinished 3BR/1BA is ready for our first guests. New kitchen with new SS appliances and W/D, new paint throughtout and new bathroom vanity/floor, refinished hardwood floors throughout. Quiet residential neighborhood. Walk to Eggs Up Grill for a great breakfast, and continue another block to restaurants, ice cream, coffee shops, etc. Be our first guests!

4.97 out of 5 average rating, 231 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, basketball and farmers market. - Short 20 minute drive to downtown Greenville - Perfect for families and those traveling for work!

Tiny home in Fountain Inn

4.94 out of 5 average rating, 390 reviews

Creative Getaway in Tropical Tiny House

Hola! Welcome to La Casita Bonita, or "the pretty little house". A perfect place for your creative getaway to write the rest of your book, work from home, read all day, or just want to get away to a new city. This sweet jungalow has two bedrooms, 5 skylights, a porch and swing to drink your coffee in the morning, Wifi and smart tv streaming, and many more little quirks and perks.

Guest house in Greenville

5 out of 5 average rating, 127 reviews

Sally's Cottage

Couples retreat located 6 miles from downtown Greenville and the Swamp Rabbit Trail in a comfortable country setting. Wake up to a beautiful woods view through a large bay window and wildlife that surrounds the cottage (deer, birds and squirrels). Experience the beauty of the country in the city! Enjoy the eclectic collection of art and design in this cute little cottage.

Superhost

Guest suite in Simpsonville

4.79 out of 5 average rating, 33 reviews

Ideal Location - Hidden Home Studio

Forget your worries in this spacious and serene space. We invite you to enjoy this newly renovated private entry lower level Studio with efficiency kitchen and full bath. Enjoy our serene backyard, full of birds and towering trees. Come here to relax, work, or both! Just 18 minutes to downtown Greenville!

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Popular amenities for Simpsonville holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Simpsonville

5 out of 5 average rating, 3 reviews

New! Yellow Jasmine Modern Living 2BR

JakeRating, 5 stars3 weeks ago

Great place to stay with a very responsive and helpful host!

Guest house in Simpsonville

4.94 out of 5 average rating, 244 reviews

Private Suite in Downtown Simpsonville

DarlaRating, 5 stars3 weeks ago

I had a great stay in Simpsonville, SC. Everyone was very helpful and polite. Thank you!

Private room in Simpsonville

5 out of 5 average rating, 9 reviews

Private room in home

EdnaRating, 5 stars2 weeks ago

Very peaceful and clean. Nice quiet neighborhood. The host was quite pleasant. I will book again.

4.97 out of 5 average rating, 97 reviews

Relaxing Cottage near downtown S’ville

SavannaRating, 5 stars3 months ago

My family needed a place to stay while my husband and I raced in a cycling event over the weekend. Definitely saving this place for future race weekends. It’s clean, cozy, spacious, and close to downtown where there’s great food and shopping.