
Holiday rentals with a pool in Williamsburg
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Williamsburg
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Wooded Wonderland Miniature Golf Hot tub Pool
Me and my family loved our stay. The pool and hot tub was great and lots of fun, we didn’t expect how deep it was. The mini golf course is a good time as well. There was so much to enjoy at the house we barely had time to go to the beach. And the host and owner were extremely friendly, and helpful.

Gorgeous Vacation House
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!

Blue Heron WaterSide
Of my many Airbnb stays, Laura’s comes up with the very best. Her home is lovely, inside and out, with a lot of fun activities to choose from. Located on a beautiful creek opening to wide water gave us a chance to explore in her kayaks and paddle board. Rainy weather meant indoor board games, reading etc on the beautiful protected porch. The kitchen had all sorts of amenities for cooking. Plenty of bedrooms for sleeping in the peaceful atmosphere. I can’t wait to return there!

Perfect Getaway!
We had a great family visit at this house. We really enjoyed the pool and whole house was very comfortable and clean! It was nice to just hang all day by the pool or top for a sanctuary from a long day of events. Sabrina was very attentive and responsive with questions and situations, appreciate her flexibility as a host!

Sunrise, North End Beach
Mark is a great host. The house is immaculate. Every little detail is perfect. By far the nicest AirBNB I have ever rented. Mark made sure everything was perfect for our visit with our son in the Navy.

The Rosé Retreat: Pool-Screened Porch-RELAX
We had a really nice stay at the Rose Retreat! The home is wonderfully appointed with nice furnishings. We especially appreciated the well stocked kitchen with upscale drink and dinnerware. The hand written welcome note, bottle of wine and snacks were so thoughtful - thank you! A perfect location from which to enjoy Irvington and the surrounding towns. We hope to come back in warmer weather to enjoy the pool!

Magical wooded cottage pool +priv hottub walk2town
We needed a peaceful, relaxing weekend away and that’s exactly what we got by choosing this AirBnB. While neighbors were close, the trees made it feel like we were secluded. The home was comfortable. We especially enjoyed the back room off the kitchen for just hanging out and chatting. Maria provided thorough details up front and was responsive during our stay. We are already planning our next trip.

Beach Home, Upscale Croatan Resort + Private Pool
Such a wonderful place!! Beverly was more than accommodating and was very responsive to all of our questions🙌🏽 we would love to stay here again in the future
Apartment rentals with a pool

Williamsburg Plantation ThanksGiving Large Condo 2
Amazing experience! communication was amazing! I'm a firm believer that communication sets the tone for an experience. The resort is beautiful! the amenities were top tier. The biweekly poolside party was a hit with the family. We felt safe and very welcomed. Great experience!

Patriots Place, one bedroom condo, cozy space
Place was as advertised. It was clean and had all the stated amenities. Comfortable place to stay while visiting family. Just a note the laundry is not in the unit but is free to use in the building.

Wyndham Patriots Place | King Bed Studio
We had a great stay here. Check in was easy and the suite had everything you need to feel at home. Staff was also very nice and helpful. Would recommend!

Relax in Style: 1BR Condo w/ Balcony at CW Governo
Hello everyone! If you never been to the Wyndham Resort in Williamsburg you have to go. Great stay, amazing scenery, and everyone is very friendly. The host I had name is Anna. Anna did an amazing job communicating with me throughout my booking process. I loved everything about resort when i stayed for 2 nights. The jet tub was amazing OMG I dont know what else to say lol. It was so fun , and peaceful to be away. One more thing the restaurants are really nice as well to go eat at. THANK YOU ANNA I REALLY APPRECIATE YOU.

Charming 1BR Colonial Condo at Wyndham Kingsgate
Working with David was great and our stay was comfortable. I would definitely stay there again.

Patriots Place 2 Bedroom
We really enjoyed our stay. Ryan was quick to respond. His place had ample room for kids and I. People at front desk were very nice and welcoming. Some things that were not in Ryan’s control, was told pool was heated and it was not. It was freezing cold. And we needed to check out late d/t sports even starting later in afternoon, and the resort would not accommodate us. Other than that great place would recommend.

Greensprings Vacation Resort 2br suite, Saturday c
We loved the location. We could easily travel around in Yorktown, Williamsburg, and Jamestown. Restaurants and shopping were just down the road.

Cozy 2BR Condo in Williamsburg
Glad we spent the extra money for this place compared to some of the larger rental companies’ condos. Nicole and Mark have added some really nice extra touches to the place like nicer towels, shower soap dispensers, and a few snacks. The place was spotless and smelled good when we walked in. Great location both in Williamsburg and this resort- we walked to the coffee shop and the playground.
Quick stats about holiday rentals with a pool in Williamsburg
Total rentals
1.6K properties
Nightly prices starting at
₹2,596 before taxes and fees
Total number of reviews
7.4K reviews
Family-friendly rentals
900 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
1K properties have a dedicated workspace
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- Chesapeake Bay
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