Vacation rentals with a pool in Winston-Salem

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Popular amenities for Winston-Salem rentals with a pool

House rentals with a pool

Top guest favorite
Home in Greensboro
5 out of 5 average rating, 13 reviews

Perfect Greensboro location Entire Townhome

NatRating, 5 stars2 months ago
Five star place in every way. Super clean. Nice layout. Classy host helpfully stocked toiletries and snacks and is great communicator. Well appointed kitchen with top notch pans etc.
Superhost
Home in Jamestown
4.8 out of 5 average rating, 46 reviews

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

KellyRating, 5 stars3 weeks 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 Greensboro
4.92 out of 5 average rating, 78 reviews

Quiet Townhouse near the airport and beltline

CherieRating, 5 stars5 days ago
The townhouse is in a great location near Guilford College. It was clean, and the neighborhood is quiet.
Guest favorite
Home in Greensboro
5 out of 5 average rating, 9 reviews

Modern and Spacious Townhome Retreat

CourtneyRating, 5 stars6 months ago
Very comfortable and clean. Perfect for what we needed since we needed to go between Downtown Greensboro and the Greensboro Convention Center.
Guest favorite
Home in High Point
4.87 out of 5 average rating, 23 reviews

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

LauraRating, 5 stars3 weeks 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 stars6 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, 32 reviews

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

JustinRating, 5 stars2 weeks ago
The apartment was immaculate. Everything was organized perfectly. The apartment was as advertised. I guess the biggest thing that impressed me the most was how Kay takes care of the little details. There is a washer and dryer in the unit, but she also took the time to make sure there were fabric softener sheets, and wash pods. In the kitchen, it was the same attention to detail. I was shocked to notice that there was a miniature selection of spices to cook with. The beds were comfortable, the bathrooms were nice, towels, soap and shampoo - everything you need in that respect. The place was wonderfully furnished. It suited our needs perfectly. and to top it off, I appreciated the fact that there was very little in the way of a to-do list upon checkout. just three simple things, take the trash out. start the dishwasher and turn The thermostat down to 68. it's a good value, + no stupid chores, I would highly recommend any location Kay offers.
Guest favorite
Home in Winston-Salem
4.93 out of 5 average rating, 15 reviews

The Humble Abode

SandraRating, 5 stars3 weeks 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 💖

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
4.55 out of 5 average rating, 29 reviews

Quiet & Cozy 3 bedroom condo

BrianRating, 5 stars10 months ago
Great price and a great price
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, 49 reviews

Peaceful Ardmore 2BR w/pool by hospitals & DT

NancyRating, 5 stars2 months ago
We really enjoyed our stat at Hawi's place in Winston Salem. It was spacious, clean and had everything we needed. The location is great and close to stores as well as Miller Park. We would love to come back during warmer weather to enjoy the porch and pool area.
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 stars8 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, 33 reviews

The Best of Benjamin

ToddRating, 5 stars1 week ago
We were in town for a soccer tournament and this was a great location and value. Enough space to spread out, cook meals, and get a good rest.
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

    $20 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

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