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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Superhost
The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.
Condo in Williamsburg
4.93 out of 5 average rating, 138 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

This beautiful, 2B2Ba condo is 1400 sq.ft. in the exclusive Kingsmill neighborhood. This 1st floor unit has two master suites w/ king beds. One features a luxurious bathroom w/ a walk-in shower & dual shower heads, the other has a shower/tub combo as well as a private patio, stepping out onto the 9th Fairway. The open-concept living space has dining for 6, a queen sleeper sofa, a fully stocked kitchen, and an additional private patio. Golf course views from anywhere in the main living space!

Top Guest favourite
Guesthouse in Gloucester
5 out of 5 average rating, 157 reviews

Creekside, Pool, Dock & Firepits, Elevated Porch

- Waterfront retreat on 10 wooded acres above Bland Creek - Immaculately clean, frequently described as spotless and pristine - Private screened-in porch with peaceful creek and marsh views - Kayaks, a floating dock, fishing, firepits, and nature right outside your door - Well-stocked kitchen plus full-size washer and dryer - Thoughtful hosting with local recommendations, guidebook, and fresh cookies - Peaceful setting just minutes from downtown Gloucester and 45 minutes from Williamsburg

Top Guest favourite
A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.
Home in Cobbs Creek
4.98 out of 5 average rating, 164 reviews

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

Top Guest favourite
The image depicts a Colonial-style resort building featuring two sections with light blue and gray siding. Lush greenery surrounds the property, with well-maintained landscaping visible. A pathway leads to the entrance, enhancing accessibility to the inviting façade.
Apartment in Williamsburg
5 out of 5 average rating, 16 reviews

Kingsgate 2BR w/ Kitchen

Furnished in the Colonial style, this resort offers all the modern amenities and activities you could want. Surrounded by the area's top attractions and historic landmarks, there's plenty to explore, ensuring that your getaway is one to remember. Located just 5 minutes from historic Williamsburg, Club Wyndham Kingsgate provides convenient access to historic attractions, wineries, beaches, and local artisan shops. Relax by the pool or indulge in the natural splendor surrounding this resort.

Top Guest favourite
A serene waterfront view features two kayaks resting on the grass under tall trees. A wooden dock extends into the water, surrounded by lush greenery and a clear blue sky. The area offers a peaceful setting for outdoor activities.
Farm stay in Cardinal
4.91 out of 5 average rating, 206 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

Superhost
An indoor swimming pool is framed by large arched windows, allowing natural light to illuminate the space. Loungers are lined along the poolside, providing a relaxing area for guests. The walls are painted in calming shades of blue and cream, enhancing the serene environment.
Condo in Williamsburg
5 out of 5 average rating, 3 reviews

Charming 1BR Colonial Condo at Wyndham Kingsgate

Welcome to our charming 1BR/1BA condo close to Williamsburg! Located just minutes from historic Williamsburg, you can explore the area or stay on property and relax by the pool and enjoy the many family friendly amenities on site. Experience all that Williamsburg has to offer from historic landmarks along one of Williamsburg's many walking and biking trails like Powhatan Creek Trail, Historic Jamestown Bike Trail, and Freedom Park, historic downtown Williamsburg, and Busch Gardens.

Superhost
An indoor swimming pool is featured with clear, blue water reflecting the vaulted ceiling. Lounge chairs line the poolside, and large windows provide ample natural light while offering views of the exterior.
Resort in Williamsburg
4.76 out of 5 average rating, 21 reviews

Charming 1BR Colonial Condo at Wyndham Kingsgate

Welcome to our charming 1BR/1BA condo close to Williamsburg! Located just minutes from historic Williamsburg, you can explore the area or stay on property and relax by the pool and enjoy the many family friendly amenities on site. Experience all that Williamsburg has to offer from historic landmarks along one of Williamsburg's many walking and biking trails like Powhatan Creek Trail, Historic Jamestown Bike Trail, and Freedom Park, historic downtown Williamsburg, and Busch Gardens.

Top Guest favourite
A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.
Farm stay in Williamsburg
4.97 out of 5 average rating, 388 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Top Guest favourite
The Gothic Revival-style cottage is showcased from its charming exterior, featuring large arched windows and a welcoming front porch. Two wooden chairs sit invitingly on the porch, complemented by seasonal decorations. Surrounding trees provide a sense of tranquility within the peaceful setting.
Cottage in Irvington
5 out of 5 average rating, 229 reviews

Peaceful Haven: nature & charming town

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.

Guest favourite
A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.
Apartment in Williamsburg
4.85 out of 5 average rating, 174 reviews

Westgate Historic Williamsburg One Bedroom

Offering a one bedroom apartment in Westgate Historic Williamsburg Resort with a king size bed, sofa bed and full kitchen. This fabulous resort has fantastic amenities and is a great location to visit the area attractions such as Colonial Williamsburg, Busch Gardens Williamsburg and Water Country USA. A great location to visit the local attractions.

Superhost
Apartment in Williamsburg
5 out of 5 average rating, 4 reviews

1BR Suite in Williamsburg @ All Inclusive Resort!

Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $100 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in.

Guest favourite
Apartment in Williamsburg
4.88 out of 5 average rating, 8 reviews

1 Bedroom Suite at Historic Resort+Amenities!

Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $100 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in.

Popular amenities for Williamsburg rentals with a pool

When is the best time to visit Williamsburg?

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Avg. price$173 NZD$181 NZD$211 NZD$220 NZD$232 NZD$242 NZD$248 NZD$222 NZD$181 NZD$206 NZD$223 NZD$195 NZD
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Quick stats about holiday rentals with a pool in Williamsburg

  • Total holiday rentals

    Explore 1,700 holiday rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 9,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,000 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,010 properties have a dedicated workspace

  • Wi-Fi availability

    1,700 of Williamsburg holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Williamsburg rentals

  • 4.7 Average rating

    Williamsburg stays receive an average rating of 4.7 out of 5 from guests

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