Vacation rentals with a pool in Winston-Salem

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Top-rated rentals with a pool in Winston-Salem

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Farm stay in Pinnacle

4.9 out of 5 average rating, 265 reviews

Beautiful Retreat at Pilot Mountain Vineyards

This quiet rancher sits right off of HWY 52 in Pinnacle, NC. The property is connected to Pilot Mountain State Park on two sides. PMSP trails can be accessed from here. Right down the road, there is a river access to the Yadkin River and horseback riding trails. Hanging Rock state park and the Dan River are only a few miles away. The historic town of Pilot Mountain is down the road. Enjoy the beautiful view of the mountain and the feel of being isolated while close to restaurants and activities

Top guest favourite

Home in High Point

4.93 out of 5 average rating, 112 reviews

Historic Street House/Hot Tub

Walking distance to Furniture Market , Hospital, Baseball Stadium, Children’s Museum, High Point University, Carolina Core Soccer, Uptowne shops, Restaurants, Breweries, Alex's House, a local breakfast diner, Dinner at Sweet Ol Bill's or the Historic JH Adams Inn. Live Music within walking distance. Nearby Greenway/Pickleball Courts. Joy Bar coffee 2 blocks away.Saturday Farmers Market. Library, Krispy Kreme, Relax on the front porch or ping pong inside! Back yard Hot Tub. 10 foot plunge pool.

Guest favourite

Home in Winston-Salem

4.9 out of 5 average rating, 308 reviews

Cozy King Blue H2O Staycation , Pool & Hot Tub

Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool (Closed until 5/23/25) . A fire pit to unwind. Back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)

Guest favourite

Townhouse in Winston-Salem

4.89 out of 5 average rating, 28 reviews

“Deacon Townhouse” 3 bedroom

Perfect Family Getaway! Discover your ideal home retreat in this spacious and comfortable accommodation, perfect for group of 6 people or families seeking memorable stay. You’ll enjoy access to fantastic community playgrounds and a refreshing swimming pool, ideal for fun-filled days. This inviting home features 3 cozy bedrooms and 2.5 bathrooms, providing ample space and privacy for everyone. Engage in friendly competition with the pool and ping pong table promising ours of entertainment.

Guest favourite

Condo in Winston-Salem

4.9 out of 5 average rating, 455 reviews

Sanctuary – 1bedroom & 1bathroom

My modern and convenient condo located in the heart of Winston-Salem’s shopping district will provide you with a 1 bedroom & bathroom space. The condo is professionally furnished and cleaned to provide a 5 star experience. Basic appliances provided (microwave, kitchen appliances, washer & dryer, dishwasher, Keurig). Very spacious with patio furniture for extra relaxation! You can also enjoy the community pool and gym. This space is NOT shared. Guests have the entire space to themselves.

Guest favourite

Home in Winston-Salem

4.97 out of 5 average rating, 63 reviews

Grey Sapphire Hideaway - 2BR/2BA w/ Arcade

Nestled along a leafy tree-lined street in a quiet neighborhood is this stylish property with all the modern comforts of home and an inviting community pool waiting for you to enjoy. Inside this modern hideaway, you’ll find plush sofas, a warm fireplace, a gourmet kitchen, king and queen bedrooms and a bright sunroom filled with a Pac-Man arcade & an air hockey table. Centrally located only minutes from Hanes Mall, Downtown Winston Salem, Medical Centers, shops, restaurants, and more!

Top guest favourite

Townhouse in Greensboro

4.95 out of 5 average rating, 108 reviews

Pearlitah: Cozy 3-BR, King Suite – Winter Escape

Nestled in a serene, semi-gated community, Pearlitah is a newly-renovated 3-BR townhouse in Greensboro that blends luxury with comfort. The master suite features a California King bed, and the home comfortably sleeps up to 9. Just 14 minutes from GSO airport, with easy highway access, and walking distance to local eateries and shops, Pearlitah offers a tranquil yet connected retreat. Ideal for relaxation and exploration, it’s the perfect home-away-from-home in this charming residence.

Top guest favourite

Guest suite in Greensboro

4.95 out of 5 average rating, 134 reviews

The Cave • Adult Getaway w/ Luxe Amenities

Tucked away in the peaceful Sedgefield PGA community of Greensboro, The Cave is a 2-bedroom, 1-bath poolside suite designed for relaxation & comfort. This serene grown-up getaway boasts luxury amenities including exclusive use of our private seasonal pool, indoor & outdoor theaters, Brunswick pool table, bar/ kitchenette, & more. Enjoy personalized service & a prime location—just minutes from top dining, shopping, golf courses, entertainment venues, sports arenas, & universities.

Top guest favourite

Guesthouse in Mocksville

4.99 out of 5 average rating, 146 reviews

Entire Private Entrance Studio Apartment with Pool

This private entrance, NOT shared, spacious open plan apartment includes a king bed, sofa, dining area, work space, plus a private full bathroom. The living space is located on the 2nd floor and the bathroom is on the ground floor. There are 15 stair steps between the 2 levels. The property is located 1-1/2 miles from downtown Mocksville and Interstate 40. Travel time is 25 mins to Winston-Salem & Wake Forest University, 22 mins to downtown Statesville, & 24 mins to Salisbury.

Top guest favourite

Home in Lewisville

5 out of 5 average rating, 16 reviews

Pool and Hot Tub | Stunning home

This beautifully staged 4-bedroom, 3,5 bath home in Lewisville, NC, sleeps 7 and offers the ultimate relaxation with a private pool, hot tub, and outdoor dining space. Inside, enjoy a spacious open-concept living area and a fully equipped kitchen. Located minutes from top wineries, a distillery, and a brewery, it’s the perfect home base for exploring local flavors. Whether you’re lounging by the pool or touring nearby attractions, this retreat has it all!

Superhost

Apartment in Winston-Salem

4.9 out of 5 average rating, 20 reviews

Luxe City Suite| King Bed|Pool|Free Parking

This is an entire luxury apartment in the heart of Winston-Salem equipped with everything you need for a comfortable stay *610 SqFt studio with half wall and curtains for privacy *King Beds & Queen Pullout in Living Room *2 Smart TVs (55" & 43") *Lightening fast Wi-Fi *Front Load Washer + Dryer Inside Unit *Free On-Site Parking *Pool & Gym *Pet Friendly (Fee $100) *Age Requirement 25+ *ID + Screening Required *100% Smoke-Free Community

Guest favourite

Guesthouse in High Point

4.81 out of 5 average rating, 155 reviews

Carolina Cowgirl Cottage

Charming cottage, newly refurbished. Cozy space w/full kitchenette, breakfast table, full bath w/shower, TV- seating area, queen bed with vaulted ceiling, professionally decorated. Pet OK w approval. walkable historic Emorywood & HP Country Club neighborhood, near HPU, hospital, park, HP Library, farmers market & HP Furniture Market. Big yard, patio & gas BBQ. Week-longterm discount. 1111 Orlando Place.