Vacation rentals with a pool in Winston-Salem

4.91 out of 5 average rating, 292 reviews

A serene view of a green landscape is provided from a covered porch. Two rocking chairs face an open yard with a small table, leading toward a rustic building in the background. A prominent mountain peak is visible in the distance under a partly cloudy sky.

Farm stay in Pinnacle

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

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Guest suite in Greensboro

The exterior view of The Cave showcases a home illuminated at dusk, featuring a well-lit pool area. A welcoming sign states 'The Cave: An Oasis for Adults.' The indoor lounge area displays a cozy setup with modern lighting and a large screen welcoming guests.

4.95 out of 5 average rating, 150 reviews

Peaceful Couples Retreat • Pool, Theatres, & More

Tucked away in the peaceful Sedgefield PGA community of Greensboro, The Cave is a 2-bedroom, 1-bath poolside GUEST SUITE designed for relaxation & comfort. This serene grown-up getaway boasts luxury amenities including exclusive use of our private seasonal (summer) 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.

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4.96 out of 5 average rating, 47 reviews

Home in Kernersville

Private Pool; HotTub; Game Room; Gym

POOL OPENS APRIL14! Experience the ultimate getaway in this spacious 5-bedroom, 4.5-bath home that sleeps up to 20 guests. Highlights include a pool, 4-person hot tub, expansive yard, and a screened-in porch. Enjoy endless entertainment in the game room with pool table and ski ball or stay active in the gym with a sauna. Perfect for reunions or retreats, this oasis is close to Winston-Salem, Greensboro, and High Point. Relax, recharge, and create unforgettable memories in this luxurious retreat!

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4.96 out of 5 average rating, 23 reviews

Home in Ardmore

Light and Bright Condo w/POOL - WFU, Atrium Hosp

About this space You will love the peaceful feel of this light filled condo with designer touches, located in walking distance to so many conveniences. Located less than 1 mile to WF Baptist Medical Center; 3.5 mile /10 min drive to WFU and NCSA. Prime shopping + dining with a 2-10 min walk to over 40 dining and shopping options including Camel City Coffee, Bagel Station, Harris Teeter grocery, and Trader Joe’s. Explore the popular Ardmore neighborhood with sidewalk lined streets and parks.

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4.93 out of 5 average rating, 81 reviews

Condo in Ardmore

Peaceful 2BR w/pool near DTWN, Hospitals, Shopping

Keep it simple at this peaceful and centrally-located condo with ample natural lighting in Ardmore. Dedicated workspace with standing desk available. King sized air mattress for living room space. Walking distance to restaurants and shopping and right around the corner from interstate. 5 min drive to downtown area. Walking distance to Atrium Health WF Baptist Health, 2 miles to Novant Health Medical Park/Forsyth Medical Center. 8 mins to Hanes mall area. ~10 min drive to Wake Forest University.

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Superhost

A striped hammock is positioned in the foreground, offering a vibrant contrast against the natural green backdrop. In the background, a sparkling pool is visible, surrounded by lounge chairs and an umbrella, set against a serene, leafy environment.

4.67 out of 5 average rating, 21 reviews

Aqua D’Lux House w/ Pool~4Rms~2kg 2qn 1f beds

•If you like to enjoy the sun, swim, water view and the tranquil surrounding without going far away from home. This lovely centrally located home is designed to provide a comfortable getaway to all diversity visitors looking for a perfect stay. • All four bedrooms has abundance of amenities along with a fantastic fresh stylish looking and plenty of natural light will provide all the relaxation you need after a long day of work♡ • Travel work is welcomed like travel nursing, and travel agents!

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A serene outdoor space is highlighted by a landscaped salt-water pool surrounded by lush greenery. Colorful flowers in pots add vibrancy, while lounge chairs and patio furniture offer inviting areas for relaxation. A wooden fence provides privacy, creating a peaceful oasis for enjoyment.

5.0 out of 5 average rating, 25 reviews

Amazing Retreat Outdoors+Indoors

I’m Tom, a design-build professional & my wife Lindy’s background is international furniture. We’ve combined our talents to create this retreat with BEAUTIFUL interior & WONDERFUL outdoor amenities: Lush landscaping, heated salt water pool (POOL IS HEATED FROM THE LAST WEEK OF APRIL THRU THE FIRST WEEK OF OCTOBER), cedar barrel sauna and hot tub. We created this retreat for ourselves but do rent it on a limited basis to other FAMILIES to create wonderful FAMILY memories. PET FEE $50 per dog.

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A private outdoor space features a round stock tank pool surrounded by a pebbled area. Two colorful inflatable pool toys rest in the water. Comfortable seating arrangements with woven chairs are paired with hammocks, creating a cozy atmosphere amidst lush greenery.

4.89 out of 5 average rating, 358 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)

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Townhouse in Winston-Salem

4.82 out of 5 average rating, 44 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.

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A modern living area features plush gray sofas positioned around a glass coffee table. Large sliding doors provide access to a wooden deck. A wall-mounted TV and electric fireplace enhance the contemporary design, while vibrant yellow drapes add a pop of color.

4.97 out of 5 average rating, 119 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!

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4.94 out of 5 average rating, 126 reviews

Home in High Point

Historic Street House/Hot Tub/Splash Pool/Chickens

3 min. drive to Furniture Market, Hospital, Truist Point Baseball Stadium, Children’s Museum. High Point University, Carolina Core Soccer 1 mile away. Uptowne shops, Restaurants, Breweries, Alex's House Diner, Toms Place, Sweet Ol Bill's, Historic JH Adams Inn less than a mile away. Weekend Live Music, Greenway/Pickleball Courts. Joy Bar coffee 2 blocks away. Farmers Market. Library, Krispy Kreme, Relaxing front porch or ping pong inside! Hot Tub. 10 foot plunge pool. Backyard chickens!

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