Vacation rentals with a pool in Winston-Salem

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Winston-Salem rentals with a pool

House rentals with a pool

Superhost
Home in Jamestown
4.8 out of 5 average rating, 46 reviews

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

KellyRating, 5 stars1 month ago
Our family was in the Greensboro area to visit family and Jeremy’s house provided a great location with plenty of space and amenities for our family of five. The beds were comfortable and the hot tub was great. Lots of golf courses near by too! We would definitely stay again in the future!
Top guest favorite
Home in Belews Creek
4.87 out of 5 average rating, 53 reviews

Belews Lake Paradise

KristiRating, 5 stars1 month ago
Perfect location for a family reunion traveling from SC, NC and VA! The property has so much to offer we didn’t need to leave the house. Indoor and outdoor dining and cooking, pool, hot tub, ping pong, covered and uncovered decks, comfortable furniture and all the amenities you need add up to an amazing place. Thank you Eli for everything! We hope to make this an annual event.
Superhost
Home in High Point
4.83 out of 5 average rating, 24 reviews

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

LauraRating, 5 stars1 month 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.
Guest favorite
Home in Jamestown
4.98 out of 5 average rating, 47 reviews

Poolside Retreat: Greensboro, High Point, Winston

SamaraRating, 5 stars7 months ago
Jay and Tia's place was phenomenal!! I pictures accurately depict the space but almost don't do it justice! It is just so beautiful, clean, roomy and welcoming! The home was spacious and smelled delicious! The neighborhood was easy to find and quiet and the back deck and yard provided more than enough room to visit, enjoy nature and have fun! Jay was proactive and thoughtful, immediately checking in with me upon arrival. He knew we intended to use the pool and even though it had been cleaned the previous day, a hurricane rolled through the night before and resulted in debris filling the pool. He was generous in offering to have the pool cleaned again the following morning so we would have at least some time to enjoy it. The hosts were very responsive, friendly, polite and accommodating and the home was wonderful. The small details like water, popcorn and hygiene items that some people had forgotten, were a nice personal touch! We would love to come back to this home again!
Top guest favorite
Home in Winston-Salem
5 out of 5 average rating, 33 reviews

Grey Sapphire Hideaway - 2BR/2BA w/ Arcade

BrittanyRating, 5 stars2 weeks ago
Great experience with Kay! Great place to stay! Would recommend!
Guest favorite
Home in Winston-Salem
4.93 out of 5 average rating, 15 reviews

The Humble Abode

SandraRating, 5 stars1 month 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 💖
Superhost
Home in Greensboro
4.87 out of 5 average rating, 45 reviews

Fun home with backyard oasis!

ChadRating, 5 stars3 weeks ago
We had a great time in Greensboro at this home. It was close to everything, clean, had awesome features, and very comfortable! Plus, the owner is great at communication. We hope to stay here again someday.
Guest favorite
Home in High Point
4.96 out of 5 average rating, 57 reviews

Your Home Away From Home

RobbinRating, 5 stars2 months ago
Our stay at Jermaine's home was wonderful as always. We enjoy the fact that the home allows us to spend time together, provides a place for us to work (when we need to), and we always feel comfortable and at home.

Condo rentals with a pool

Condo in Clemmons
4.92 out of 5 average rating, 169 reviews

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

KevinRating, 5 stars18 months ago
Thaddeus was the best host I have had to date. Over delivered in every category!
Condo in High Point
4.57 out of 5 average rating, 30 reviews

Quiet & Cozy 3 bedroom condo

KimberlyRating, 5 stars2 weeks ago
Isaac was very open and supportive of our stay. We recently relocated from Florida and he allowed us to extend our stay as needed. Just been very kind and generous. We will stay again
Top guest favorite
Condo in Greensboro
5 out of 5 average rating, 9 reviews

Mid-Century Modern Condo

JennRating, 5 stars1 month ago
Very quiet and cozy. It was very close and convenient to the activities my friend and I had planned for the weekend. I forgot to pack my travel fan for sleeping but we found a fan in each closet which was a life saver! This place was a perfect find.
Guest favorite
Condo in Ardmore
4.9 out of 5 average rating, 50 reviews

Peaceful Ardmore 2BR w/pool by hospitals & DT

StephanRating, 5 stars3 weeks ago
I stayed there four days with a colleague during a business trip. We really enjoyed the stay in this very clean and nicely equipped flat. The surronding is clean and quite and there is a Park quite close buy for smaller running.
Guest favorite
Condo in Winston-Salem
4.9 out of 5 average rating, 68 reviews

Amazing Stay In Winston Salem, Close to Everything

SarahRating, 5 stars8 months ago
This was my fourth or fifth stay at Anthony’s place. It’s become my go to whenever I visit Winston Salem for work. I like that it’s close to the highway so it’s really easy to get anywhere. His location is quiet and private, and it’s always extremely clean.
Guest favorite
Condo in High Point
4.97 out of 5 average rating, 202 reviews

Modern/Retro Luxury Condo

Taylor ThuyRating, 5 stars9 months ago
Don was an amazing host. He was very responsive, even at 11pm at night and offered to hop on over to help with an issue I had. His place was very clean, and location was just a short drive away from so many restaurants and things to do.
Guest favorite
Condo in Greensboro
4.97 out of 5 average rating, 34 reviews

The Best of Benjamin

NoumanRating, 5 stars2 days ago
It was a very comfortable stay and felt right at home! My family and I had everything we needed and more. We attended a wedding and the Airbnb was perfect for us to stay and rest after wedding events. We would absolutely recommend and will be back to stay!
Guest favorite
Condo in High Point
4.88 out of 5 average rating, 51 reviews

Heaven in High Point / Luxury 1bd/1ba

JamelRating, 5 stars19 months ago
Don’s place was as described. Clean quite area. Don was very responsive and helpful. Gave recommendations. The place had everything we needed and more. Would stay again

Quick stats about vacation rentals with a pool in Winston-Salem

  • Total rentals

    60 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    2K 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

Destinations to explore