Vacation rentals with a pool in Winston-Salem
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winston-Salem
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winston-Salem rentals with a pool
House rentals with a pool
Home in Greensboro
4.92 out of 5 average rating, 12 reviewsThe Scott Luxe Villa w/ HotTub, FirePit, Pool!
Home in Greensboro
5 out of 5 average rating, 9 reviewsPerfect Greensboro location Entire Townhome
Home in High Point
5 out of 5 average rating, 4 reviewsSpacious Home in High Point with a Pool
Home in High Point
5 out of 5 average rating, 11 reviews5BD Family Oasis | Pool | FirePit | Bball | Pong
Home in Jamestown
4.98 out of 5 average rating, 46 reviewsMidcentury Poolside Retreat Near High Point
Home in Winston-Salem
5 out of 5 average rating, 8 reviewsGrey Sapphire Hideaway - 2BR/2BA w/ Arcade
Home in Stokesdale
4.94 out of 5 average rating, 17 reviews5 Star Weddings, Outdoor Movies, Early/Late CheckN
Home in Winston-Salem
4.93 out of 5 average rating, 14 reviewsThe Humble Abode
Condo rentals with a pool
Condo in Clemmons
4.92 out of 5 average rating, 169 reviews2br King-Queen/2ba/Pool/ No cleaning fees!
Condo in Ardmore
4.89 out of 5 average rating, 45 reviewsPeaceful Ardmore 2BR near hospitals & 5 mins to DT
Condo in Winston-Salem
4.9 out of 5 average rating, 68 reviewsAmazing Stay In Winston Salem, Close to Everything
Condo in Greensboro
5 out of 5 average rating, 16 reviewsThe Best of Benjamin
Condo in High Point
4.88 out of 5 average rating, 51 reviewsHeaven in High Point / Luxury 1bd/1ba
Quick stats about vacation rentals with a pool in Winston-Salem
Total rentals
50 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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