
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
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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!

Cute Remodeled Rancher w/ Fenced in Yard and pool
Davina was very attentive and was always checking in to make sure things were going well. She quickly responded to messages and was very helpful.

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.
Apartment rentals with a pool

Charming 2BR Colonial Condo at Wyndham Kingsgate
We enjoyed our stay and can’t wait to return!

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!

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach
Excellent place to enjoy the beach. Very convenient to get to and a great parking spot. Literally steps from the north end of the boardwalk, and we really appreciated the grassy sitting area with chairs in addition to the beach access. Nice little pool right outside the unit. Also enjoyed the beach gear and the access to bikes. Space was small but comfortable, just right for two people with good A/C and a dehumidifier. Would love to stay there again!

Charming 1BR Colonial Condo at Wyndham Kingsgate
The room was clean and large enough for our family of 3. Resort amenities stood out. Pools were great and we got to enjoy the pool deck party. Reception staff were efficient and friendly, even when I declined the timeshare presentation. Overall, would stay again if visiting Williamsburg.

2br Deluxe Colonial Condo Fun For Whole Family!
The place was exactly what was described!! Lots of amenities including 3 pools, putt putt golf, arcade and more all included with your stay. My family and I will definitely stay here again. We love this place! Andrew was a very responsive host and very informative.

Williamsburg Vacation Villages Resort 2BR, 2BA
It was a great stay! Easy access to all of Williamsburg!

Wyndham Patriots Place | King Bed Studio
David’s place was great. The grounds are beautiful, the unit itself was clean and roomy, the bathroom was spotless, and the kitchenette was equipped with a coffee maker, refrigerator, small oven with stove top, microwave, some cups, and dishes. The bed and couch were comfortable as well. Reception had no problem checking us in a little before 10pm and allowed us to store our bags there after checkout. The unit itself is part of a timeshare, but honestly the staff member was not too pushy in asking if we wanted to come see a presentation (we declined). The place is a little far to recommend walking from Colonial Williamsburg, however, by car it is only 5-6 mins away. David was a responsive host and I’d stay 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.
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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