Holiday rentals with a pool in Winston-Salem

4.9 out of 5 average rating, 272 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

4.91 out of 5 average rating, 22 reviews

A light-filled living area features a plush gray sofa and two blue accent chairs, arranged around a circular table. Art with fluid patterns adorns the wall, complemented by natural light streaming through two windows, framed by soft orange drapes.

Flat in Winston-Salem

Downtown WS Walkable Suite• King Bed• Free Parking

Stay in style in the heart of Downtown Winston-Salem steps from 4th Street dining, Truist Stadium, & the Benton Convention Center. This modern 1-bedroom suite features a king bed, full kitchen, fast Wi-Fi, and in-unit laundry, plus access to a pool, gym, and free parking. *Studio with half wall & curtains for privacy *Queen Pullout in Living Room *2 Smart TVs (55" & 43") *Lightening fast Wi-Fi *In-Unit Laundry *Pool & Gym *Age Requirement 25+ *ID + Screening Required *100% Smoke-Free Community

4.92 out of 5 average rating, 61 reviews

A spacious living area features a comfortable, light gray sectional sofa positioned near a wall-mounted television. A modern fireplace is visible, and large sliding glass doors lead to a small balcony. Natural light floods the space through multiple windows.

Apartment in Ardmore

Peaceful Ardmore 2BR 5 min to hospitals & downtown

Keep it simple at this peaceful and centrally-located condo with ample natural lighting in Ardmore. Dedicated work space in bedroom with double bed (pictures to be updated soon). Walking distance to restaurants and shopping and right around the corner from interstate. 5 min drive to downtown area. Walking distance to Atrium Health Wake Forest Baptist Health, less than 2 miles to Novant Health Medical Park/Forsyth Medical Center. 8 mins to Hanes mall area. ~10 min drive to Wake Forest University.

A contemporary living area is highlighted by a plush, emerald green sofa adorned with yellow accent pillows. A sleek coffee table sits on a patterned rug, illuminated by natural light from nearby sliding glass doors. Modern decor includes a wall art piece and stylish lighting fixtures.

4.95 out of 5 average rating, 86 reviews

Emerald Retreat - Central & Stylish - 2 BR/2 BA

Centrally located, yet away from the hustle and bustle is this contemporary styled condo ideal for families, couples and professionals with downtown, supermarkets, medical centers and great food all just mins away. Nestled within a leafy community, the condo features chic design, spacious living, a fully equipped kitchen, 2 beautiful bedrooms, 2 modern bathrooms and a private patio. You’ll be mins from Hanes Mall, Forsyth Tech, Novant and Wake Forest Medical Center, shops and many restaurants.

The outdoor space features a private hot tub surrounded by lush greenery and a wooden deck. A circular above-ground pool is situated nearby, separated by low wooden panels. The area is complemented by garden beds with foliage, creating an inviting and peaceful retreat.

4.93 out of 5 average rating, 113 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.

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.

4.9 out of 5 average rating, 317 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)

Townhouse in Winston-Salem

A cozy corner offers two armchairs on a light wood floor, complemented by a small, modern table. A wall clock is mounted above the table, and sheer white curtains frame the window, allowing natural light to enhance the room's neutral tones.

4.87 out of 5 average rating, 31 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 suite in Greensboro

A spacious entertainment area features a pool table in the foreground, with colorful balls arranged on the felt. In the background, a large screen displays a welcome message, surrounded by comfortable seating and soft lighting from modern fixtures.

4.95 out of 5 average rating, 136 reviews

The Cave ~ An Adult Getaway with 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 (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.

Apartment in Winston-Salem

A comfortable living room features a light-colored sofa set with decorative cushions. A central ottoman sits atop a soft area rug. Large windows allow natural light to brighten the space, complemented by the soft illumination from a ceiling fan. Potted plants add a touch of greenery.

4.9 out of 5 average rating, 458 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.

4.95 out of 5 average rating, 110 reviews

The front entrance of the townhouse is framed by vibrant flowers, showcasing red blooms against a backdrop of lush greenery. The inviting façade features a welcoming porch with two large windows, along with neat brick and siding detailing, creating a charming first impression.

Townhouse in Greensboro

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.

5 out of 5 average rating, 5 reviews

Home in Ardmore

Ardmore HotTub Firepit Washer Dryer Hospital 3 min

Enjoy a peaceful retreat in this spacious walkout basement apartment, ideally located across from Miller Park and just five minutes from the best of Winston-Salem. Toddler Friendly with cabinet locks, door locks, pac n play, and toddler items. Perfect for small families or couples, this home features a fully fenced backyard, a relaxing hot tub upgrade package available, and plenty of entertainment options. Perfect for travel workers, relocation housing, and meeting up with friends.

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 out of 5 average rating, 11 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.

Popular amenities for Winston-Salem rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 25 reviews

A comfortable living room setup is featured with a gray sofa adorned with various pillows. A matching armchair complements the space, which is warmly lit by a standing lamp. A round coffee table sits on a soft rug, with sunlight filtering through windows adorned with light curtains.

Home in Greensboro

Perfect Greensboro location Entire Townhome

4.89 out of 5 average rating, 63 reviews

The exterior of a newly renovated two-story home is highlighted, featuring a wrap-around porch and a symmetrical layout. The porch is bordered by manicured shrubs and small trees. Stairs lead to the central entrance, while large windows add natural light to the façade.

Home in Belews Creek

Belews Lake Paradise

4.93 out of 5 average rating, 82 reviews

A spacious living area features a coral-colored sectional sofa and a classic stone fireplace. Natural light filters through the large windows, highlighting decorative mirrors and artwork on the walls. An upper loft is visible, adding dimension to the open layout.

Home in Greensboro

Quiet Townhouse near the airport and beltline

4.6 out of 5 average rating, 96 reviews

A gas-heated pool is surrounded by a red patio and lush greenery. The crystal-clear water reflects the sunlight, creating serene ripples. The pool's unique shape is complemented by a mosaic tile border, inviting relaxation and enjoyment.

Home in Jamestown

Theater, heated pool/hot tub near HPU/Market

An aerial view of a spacious backyard reveals a large blue swimming pool surrounded by a patio area. The deck is equipped with seating and overlooks vibrant greenery. The house features a sturdy brick exterior with a balcony area providing shaded space.

4.91 out of 5 average rating, 89 reviews

Relaxing Getaway w/ Pool,HotTub,Fire Pit, Foosball

5 out of 5 average rating, 14 reviews

A welcoming living area features a variety of seating options, including a classic sofa and an armchair. A fireplace contributes a sense of warmth, while natural light streams through the windows, illuminating the laminate flooring.

Home in Clemmons

Village Brook

A spacious outdoor area features a large swimming pool surrounded by lounge chairs. A wooden fence encloses the yard, which includes a play area and accessible pathways. The backdrop displays a multi-story house and lush green trees, all under a vibrant sunset sky.

4.92 out of 5 average rating, 12 reviews

Pickleball, Basketball, Movie Theater, King Beds

A stylish living room features a spacious black sectional sofa, accented with colorful throw pillows. A sleek coffee table sits on a soft area rug, with light streaming through large windows. The adjoining dining area, visible in the background, includes a wooden table and chairs.

4.91 out of 5 average rating, 33 reviews

Modern, Relaxing, Peaceful home near Mkt and HPU

Apartment rentals with a pool

The living room features a comfortable brown leather sofa and a pair of matching chairs. A television is placed on a media unit, while light enters through large glass doors. Decorative items and framed photographs enhance the cozy ambiance of the space.

Apartment in Clemmons

4.92 out of 5 average rating, 169 reviews

2br King-Queen/2ba/Pool/ No cleaning fees!

Apartment in Winston-Salem

5 out of 5 average rating, 8 reviews

Located near WFU, Baptist, & Forsyth Hospital‼️

4.97 out of 5 average rating, 202 reviews

A modern kitchen features sleek black cabinetry and stainless steel appliances. An elegant round dining table occupies the center, surrounded by transparent chairs. Blue accent walls complement the minimalist design, while soft lighting from pendant fixtures enhances the ambiance.

Apartment in High Point

Modern/Retro Luxury Condo

4.82 out of 5 average rating, 61 reviews

Apartment in Greensboro

Comfy townhouse near airport and dining!

Apartment in High Point

5 out of 5 average rating, 5 reviews

3BR/2 bath Condo Near Downtown HP&HPU sleeps 6

The living room features a cozy seating arrangement with a leather sofa and two wooden armchairs, accompanied by a circular coffee table. A textured area rug lies beneath, and a wooden fireplace is set against a diagonal wood-paneled wall, enhancing the warm ambiance.

Apartment in Winston-Salem

Charming Condo - Near WFU and Hospitals, Fast WiFi

Other holiday rentals with a pool

5 out of 5 average rating, 18 reviews

Home in Lewisville

Gorgeous house… with hot tub and pool

A peaceful outdoor area with a gravel path is surrounded by colorful flowers and a stone fire pit. A cozy reading nook features a comfortable chair and wooden shelf with books. A spacious bedroom offers a queen bed with natural light from a window. A refreshing pool area showcases lounge chairs and a clean pool inviting for relaxation.

Guest suite in Thomasville

4.88 out of 5 average rating, 118 reviews

The Haven

A well-maintained pool area is surrounded by lush greenery and vibrant flower beds. Comfortable lounge chairs and a shaded seating area are positioned nearby, creating a relaxing outdoor space. Natural elements and tropical plants enhance the serene atmosphere of the backyard.

Place to stay in Archdale

4.68 out of 5 average rating, 215 reviews

Private Peaceful Cottage & Serene Gardens

A spacious living area features a large sectional sofa in soft brown fabric, complemented by a minimalist wooden coffee table. Floor-to-ceiling windows allow natural light to flood the room, offering views of the surrounding trees. A dining area with tall chairs is visible in the background.

5 out of 5 average rating, 3 reviews

Rosewood Loft | Entire Building

A clear swimming pool is framed by a concrete deck. The water reflects a vibrant blue, surrounded by green grass and a low fence in the background. Comfortable lounge chairs are positioned nearby, adding to the space for relaxation.

Home in Greensboro

4.9 out of 5 average rating, 151 reviews

Remodeled Oasis in the heart of Greensboro

Guest house in Mocksville

A clear blue swimming pool is framed by a brick border, featuring a small rock fountain. Red umbrellas provide shade over black patio tables and chairs arranged nearby, with well-maintained landscaping surrounding the area. The back of a light-colored house is visible in the background.

4.99 out of 5 average rating, 146 reviews

Entire Private Entrance Studio Apartment with Pool

A light-filled living area features a comfortable sofa with decorative cushions, a wooden coffee table, and two stylish lamps. An abstract painting hangs above the sofa, and a patterned area rug adds warmth to the hardwood flooring. Natural light streams through the window, complemented by soft curtains.