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 favorite

Farm stay in Pinnacle

4.9 out of 5 average rating, 258 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 favorite

Condo in Ardmore

4.91 out of 5 average rating, 55 reviews

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.

Superhost

Home in Winston-Salem

4.89 out of 5 average rating, 292 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 favorite

Apartment in Ardmore

4.94 out of 5 average rating, 32 reviews

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!

Guest favorite

Condo in Winston-Salem

4.91 out of 5 average rating, 447 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.

Top guest favorite

Home in Winston-Salem

5 out of 5 average rating, 48 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!

Guest favorite

Home in Mayodan

4.92 out of 5 average rating, 256 reviews

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!

Top guest favorite

Guest suite in Greensboro

4.95 out of 5 average rating, 128 reviews

Come Cool Off @ The Cave • Luxe Amenities & More

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 favorite

Guesthouse in Mocksville

4.99 out of 5 average rating, 140 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.

Superhost

Home in Winston-Salem

5 out of 5 average rating, 3 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, salt water pool, cedar barrel sauna and hot tub. We created this retreat for ourselves with no intention of renting it but have recently decided to share our Winston-Salem home with other FAMILIES to create wonderful FAMILY memories.

Guest favorite

Apartment in Winston-Salem

5 out of 5 average rating, 7 reviews

Immerse in Local Culture

This thoughtfully restored industrial landmark blends historic character with modern luxury. Steps from the city’s top attractions, it offers a rare mix of urban energy and refined retreat. Enjoy elevated amenities, including a private bowling alley, rooftop BBQ with skyline views, a cutting-edge cardio studio, serene yoga space, and a fully equipped fitness center—crafted for those who appreciate timeless design and contemporary comfort.

Guest favorite

Guesthouse in High Point

4.81 out of 5 average rating, 154 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