Holiday rentals with a pool in Winston-Salem

4.9 out of 5 average rating, 253 reviews

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, 54 reviews

Apartment in Ardmore

Peaceful Ardmore 2BR w/pool by hospitals & DT

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.

4.93 out of 5 average rating, 61 reviews

Home in Winston-Salem

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.

4.84 out of 5 average rating, 56 reviews

Flat in Winston-Salem

Earthbound Escape

Located in a private community, Earthbound Escape is a keyless entry apartment in a peaceful, family-friendly neighborhood. Unwind in the comfort of this 1 bedroom apartment decorated in soothing earth tones. There’s free dedicated off-street parking, a futon for an extra guest, WiFi, and the apartment is conveniently located near every type of shopping you can imagine (and a few splendid restaurants). Perfect location for traveling nurses - proximity to hospitals is approximately 3 miles.

4.89 out of 5 average rating, 291 reviews

Home in Winston-Salem

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

4.9 out of 5 average rating, 20 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.

4.93 out of 5 average rating, 29 reviews

Flat in Ardmore

Clean & Cozy Condo | 4 Mins to WF Baptist | 2Kings

Keep it simple at this peaceful and centrally-located place. Convenient 4 min drive/20 min walk to WF Baptist Medical Center. Prime location for shopping + dining with a 4-9 min walk to Camel City Coffee, Bagel Station, Harris Teeter grocery, etc. High speed WiFi, 3 smart TVs logged into streaming apps, fully stocked kitchen, premium king mattresses & linens, blackout shades, dining area, free off-street parking, community pool, & more. A popular spot for traveling medical professionals!

Apartment in Winston-Salem

4.91 out of 5 average rating, 444 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 suite in Greensboro

4.94 out of 5 average rating, 126 reviews

Relax & Unwind @ The Cave • 6.5 mi to Coliseum

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 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.

4.92 out of 5 average rating, 255 reviews

Home in Mayodan

Home away from home.. 20 minutes-Greensboro/Triad

Home away from home! Relax and Enjoy! Walk to the park or downtown for a late night stroll & dinner! The home has 4 bedrooms, 2 full bathrooms with hot tub, a large deck, and covered parking spaces. Fully equipped kitchen with stainless gas range, SS Refrigerator, Vented microwave! Walk in Pantry! Formal Dining Room seating 8! Hardwoods throughout! Living room w/sectional couch! Every room has Roku Tv's! ! Salt water pool is Open May-September! Owner is a NC Broker. Inquire now!

Guest house in Mocksville

4.99 out of 5 average rating, 135 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.

Guest house in High Point

4.81 out of 5 average rating, 153 reviews

Private cottage, pet-friendly

Affordable modern cottage, steps from B&B, next to private pool. Queen bed, full kitchenette, breakfast table, full bath w/shower, sofa seating area. Spacious room with vaulted ceiling, professionally decorated. Smart TV. Pet OK w approval, walkable historic Emorywood & HP Country Club neighborhood, near hospital, park, Library, farmers market & HPU. Big deck, patios & gas BBQ. Week-longterm discount. 1111 Orlando

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Popular amenities for Winston-Salem rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.82 out of 5 average rating, 50 reviews

Home in Jamestown

Heated Pool | Hot-tub | Pool Table | King Beds

LisaRating, 5 stars2 weeks ago

The house was spacious, beautiful, and clean. The living room couch was super comfortable and provided room for everyone. We loved have Roku in basically every room/bedroom, made life easier with the kids. The beds were very comfortable with lots of pillows. My only recommendation would be to add some more throw blankets as most of the house runs cold. The room above the garage that has 2 beds runs a little warm though and those blankets were the best, so soft and comfortable. The outdoor space was beautiful. The deck is huge and great for hanging out on, the in ground pool was clean and pretty and the hot tub was great! We ran into an issue with the pool heater and Jeremy was incredibly understanding and responsive. Another bonus is the backyard is completely fenced in. All around it was a perfect space for 2 families of 4 to vacation!

5 out of 5 average rating, 9 reviews

Home in High Point

Beautiful 5BR High Point Home

ErnestRating, 5 stars13 months ago

We came for my daughter’s graduation at Wake Forest. We would have preferred to stay in Winston-Salem, but there was nothing available. This AirBnB is about 1/2hr from campus, so not too bad. There are a lot of chain restaurants and supermarkets nearby. The house itself is very roomy. The kitchen is well stocked with almost every small appliance, pots/pans, baking sheets you can think of. The Master bedroom on the first floor was huge. There are 4 bedrooms upstairs, but only 1 full bath, which we felt there should be a second bathroom upstairs. The upstairs loft was huge, and the 4 recliners were very comfy. The neighborhood is residential, and we saw a lot of families when we went for a stroll. It was more fun and economical to be together in the AirBnB versus multiple hotel rooms for multiple days. We didn’t explore High Point, so can’t say if there are any interesting attractions nearby. Overall, we enjoyed our stay here!

5 out of 5 average rating, 37 reviews

Home in Greensboro

Forest Valley Entire Home + Private Pool + Hot Tub

PhoebeRating, 5 stars6 days ago

We had a great stay at Tiffany’s place. Conveniently located near the airport. Had everything we needed, great outdoor space. Beds were comfortable, nice water temperature in the showers. Very comfortable stay for our family of 4.

5 out of 5 average rating, 39 reviews

Home in Greensboro

Roomy,Open,Pool access,King Suite,20 mins to Elon!

LashondaRating, 5 stars1 week ago

It was an amazing stay. The place was beautifully decorated, spacious and just all around a peaceful atmosphere. It was close enough to drive into town and near by cities. The host was super responsive with any questions made everything so clear and direct for easy check in. Great space and would highly recommend as well would definitely stay again when I come to the area.

4.76 out of 5 average rating, 25 reviews

Home in High Point

5BD Family Oasis | Pool | FirePit | Bball | Pong

LauraRating, 5 stars2 months ago

We were there in early spring so could not take advantage of all of the amenities. I am not sure the mini basketball court is mentioned in the description. So cute! My husband loved the firepit and grilled chicken one night. House is in an established neighborhood.

4.94 out of 5 average rating, 18 reviews

Home in Stokesdale

5 Star Weddings, Pool!, Early Chck, Nearby Fishing

ZoeRating, 5 stars7 months ago

Beautiful, quiet location with lots of amenities. We had an issue with the lock, but it was addressed very quickly and professionally. Great stay - fall colors in the trees were gorgeous, but with the pool, it'd be a great place to stay in the summer.

4.93 out of 5 average rating, 15 reviews

Home in Winston-Salem

The Humble Abode

SandraRating, 5 stars2 months ago

oh my goodness! Ashley was a phenomenal host, and went above and beyond helping us with resources for finding homes (as we are relocating to the area) and recommendations for areas she thought we'd enjoy. she was very quick to respond and truly made us feel like family in her beautiful haven of peace and tranquility. everything was awesome and so was she. thank you for a truly memorable experience 💖

5 out of 5 average rating, 6 reviews

Home in Summerfield

Modern Farmhouse | 4 BR | 4 BA | Sleeps 10 | Pool

SharifaRating, 5 stars1 month ago

INVITING!! This home was absolutely beautiful. There were so many unique touches that sparked conversation and made the experience memorable. YES! I’m holding back but it’s a lot of stunning conversational pieces. My daughter graduated from NC A&T and Ms.Ryan was amazing, kind, responsive, super friendly and so welcoming. She went the extra mile to accommodate my guest for a dinner party. She even had the tablecloth with the school colors laid out. Which made it extra special. This was my 1st time using Airbnb and OMG!! Ms. Ryan I couldn’t have asked for a better host. From the bottom of my heart I Appreciate everything you have done. Thank you. I Highly Recommend!!

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Apartment rentals with a pool

Apartment in Clemmons

4.92 out of 5 average rating, 169 reviews

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

KevinRating, 5 stars20 months ago

Thaddeus was the best host I have had to date. Over delivered in every category!

4.98 out of 5 average rating, 41 reviews

Apartment in Greensboro

The Best of Benjamin

TrevorRating, 5 stars1 week ago

Tiffany was a great host! Responded quickly when needed. The condo was clean and had all the amenities needed. Thank you for a lovely stay!