
Vacation rentals with a pool in Winston-Salem
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Winston-Salem

Total vacation rentals
Explore 70 vacation rentals in Winston-Salem

Nightly prices starting at
Winston-Salem vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 2,300 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Winston-Salem vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winston-Salem rentals

4.6 Average rating
Winston-Salem stays receive an average rating of 4.6 out of 5 from guests
Top-rated rentals with a pool in Winston-Salem
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Modern/Retro Luxury Condo
Unique condo with brand new Ultra Modern renovation with a touch of Retro. If you seek an Extremely Clean, Modern Luxurious place close to everything then this is it. My place is in walking distance to all shopping and restaurants. High Point University only ( 1.8miles ), HP Furn Market is only ( 2.3 miles ).Kitchen is fully stocked, all luxury linens, shampoo, soap, toilet paper are included. Hearing impaired doorbell. Led TV's with Netflix,Amazon & whatever channels come in on regular antenna.

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

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!

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.

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.

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.

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)

“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.

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!

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!

Townhouse near the Airport
Welcome to my home! Ideally located just 5 minutes away from the PTI airport, this home boasts a convenient main level primary bedroom with Spacious Living Room and Kitchen. Upstairs, you'll discover a cozy and inviting loft, a second bedroom, and a bathroom. The home also includes a well-equipped kitchen, perfect for cooking your own meals or eating taking out. The living room features a cozy fireplace and Apple TV for your entertainment. I look forward to hosting you!
Popular amenities for Winston-Salem rentals with a pool
House rentals with a pool

Perfect Greensboro location Entire Townhome

5 Min to High Point Market | Sleeps 8 | Near HPU

Belews Lake Paradise

2 Private Suites | Very Clean | Pool | Fast Wifi

Lakefront Retreat with Private Indoor Heated Pool

The Lodge at Kiser Mill

6BR Greensboro home with Pool. 3 miles from I-85

Guest House Excelsior at Tanglewood
Condo rentals with a pool

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

Location, Location, Location /Pool/2BR King Stay

Sanctuary – 1bedroom & 1bathroom

Comfy townhouse near airport and dining!

3BR Condo w/ Pool Near HPU & Market + Desk

Executive Golf Retreat — 18th Hole, Bermuda Run
Other vacation rentals with a pool

Remodeled Oasis in the heart of Greensboro

Entire Private Entrance Studio Apartment with Pool

2B/1.5B townhome cls to HPU/FRN Mkt Wth King bed

Lovely and Amazing Newly Renovated Townhouse

Modern Executive Townhome • Sleeps 6•Pool•FastWiFi

Guest House at Tall Tree Manor

Lazy Oak Lane Peace & Quiet

Bridford & Co.
When is the best time to visit Winston-Salem?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $159 CAD | $160 CAD | $153 CAD | $174 CAD | $162 CAD | $171 CAD | $153 CAD | $159 CAD | $153 CAD | $165 CAD | $169 CAD | $178 CAD |
| Avg. temp | 4 °C | 6 °C | 10 °C | 15 °C | 20 °C | 24 °C | 26 °C | 25 °C | 22 °C | 16 °C | 10 °C | 6 °C |
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- North Carolina Zoo
- Hanging Rock State Park
- Wake Forest University
- Zootastic Park
- Pilot Mountain State Park
- Greensboro Science Center
- Wet'n Wild Emerald Pointe Water Park
- Greensboro Coliseum Complex
- Stone Mountain State Park
- Fairy Stone State Park
- Lazy 5 Ranch
- Elon University
- University Of North Carolina At Greensboro
- Lake Norman State Park
- Childress Vineyards
- Guilford Courthouse National Military Park
- Cherry Treesort
- International Civil Rights Center & Museum
- Reynolda Village Shops & Restaurants
- Shelton Vineyards
- Greensboro Arboretum
- Andy Griffith Museum
- Martinsville Speedway
- High Point City Lake Park





