Vacation rentals with a pool in Williamsburg

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Williamsburg

  • Total vacation rentals

    Explore 1,680 vacation rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg vacation rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 10,900 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,090 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    990 properties have a dedicated workspace

  • Wi-Fi availability

    1,680 of Williamsburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Williamsburg rentals

  • 4.8 Average rating

    Williamsburg stays are highly rated by guests—averaging 4.8 out of 5!

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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Top guest favorite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Condo in Williamsburg
4.95 out of 5 average rating, 221 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

Top guest favorite
A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.
Home in Gloucester Point
4.99 out of 5 average rating, 222 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

Top guest favorite
A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.
Barn in Cobbs Creek
4.95 out of 5 average rating, 143 reviews

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Top guest favorite
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, 175 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 favorite
Home in Cobbs Creek
4.91 out of 5 average rating, 181 reviews

Million $ Views! Pool! Private Hot Tub! EV Charger

Welcome to The Cottage at Misti Cove, where the Piankatank River is just steps from your door. Wake to sunrise views from bed, paddle the river by kayak or paddleboard, and unwind in your private waterfront hot tub as evening settles over the water. Enjoy the peaceful setting of a small community along with a seasonal pool, beach, pier and tennis court. It’s a cozy waterfront escape with exceptional views, thoughtful comforts and plenty of ways to slow down and say, “Now this is the life.”

Superhost
Home in Irvington
4.95 out of 5 average rating, 180 reviews

Magical wooded cottage pool +priv hottub walk2town

Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Guest favorite
A roller coaster is depicted in motion, showcasing riders on a track that curves downwards, next to a large wooden structure resembling a water ride. Surrounding green trees provide a natural backdrop, contributing to the lively atmosphere of the amusement area.
Townhouse in Williamsburg
4.89 out of 5 average rating, 46 reviews

3bdr Williamsburg Townhouse, sleeps 8

Discover Historic Powhatan, a Hilton Vacation Club managed property, in Williamsburg, Virginia. Nestled amidst timeless beauty, our resort offers a unique blend of history and modern comfort. Explore nearby historic sites, unwind by the pool, or embark on a culinary journey in our on-site restaurant. Experience a stay that bridges the gap between the rich heritage of Williamsburg and the indulgence of contemporary relaxation. 1,736sq ft 3BDR, 2BTH, 3-STORY SUITE

Superhost
Two figures in historical military uniforms with distinctive red coats are shown standing together. The background features a building with a bright sky, while a British flag is visible nearby, suggesting a reenactment or historical event.
Condo in Williamsburg
4.72 out of 5 average rating, 147 reviews

Great family vacation resort condo. Sleeps 12.

Welcome to Greensprings Vacation Resort. We combine two adjacent 2BDR/2BA units to create one huge 4BDR unit with 2 full kit/dining and 2 LR, each with a queen sofa sleeper. And we are near everything! Busch Gardens 7 miles (10-15 minutes) Colonial Williamsburg 5 miles (8 minutes ) Water Country USA 7 miles (10-15 minutes) Historic Jamestowne 5 miles (8 minutes) Newport News/Williamsburg International Airport 19 miles (30 minutes)

Top guest favorite
Guesthouse in Gloucester
5.0 out of 5 average rating, 199 reviews

Cozy Fall Retreat - Creek Views & Fire Pits

A cozy waterfront escape tucked into 10 wooded acres above Bland Creek. Perfect for crisp fall days and peaceful evenings. - Elevated screened porch with colorful water and wooded views - Creekside fire pits for crisp fall nights - Dock, kayaks, fishing, and direct water access - Outdoor dining and hammocks beneath the trees - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

Guest favorite
Home in Hampton
4.91 out of 5 average rating, 138 reviews

4BD home w/ game room & pool near Langley & PTC!

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!

Top guest favorite
Condo in Williamsburg
4.98 out of 5 average rating, 41 reviews

3 Bed, 3 Bath Sleeps 8 in Kingsmill

Welcome to your luxurious retreat at Kingsmill on the James River. This spacious and elegantly appointed 3-bedroom, 3-bathroom condominium is located on the serene first floor, offering refined comfort in a private, gated community, overlooking the 9th fairway of the famed Kingsmill River Course. For smaller groups, we also have a 2 bed, 2 bath option available. Please, no parties or pets.

Superhost
A serene river view is captured at sunset, showcasing vibrant hues of orange, pink, and purple across the sky. A wooden pier extends into the water, backed by silhouetted trees. The calm surface reflects the colorful sky, creating a tranquil atmosphere.
Guesthouse in Gloucester
4.93 out of 5 average rating, 121 reviews

Clay Bank River Front Cottage

Recently updated waterfront cottage 2 bedroom - 2 queen beds, a pull out sofa, 28 private acres on the York River in Gloucester, Va. Great remote getaway with a pool, kayaks and private pier for fishing/crabbing. Lightly traveled river. Access to Yorktown, Newport News, Williamsburg, Jamestown, Richmond, Norfolk, Urbanna. Shares the property with the main house where owner lives.

Popular amenities for Williamsburg rentals with a pool

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Avg. price€85€91€100€114€116€119€122€109€89€97€102€83
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