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Vacation 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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Top guest favourite
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
4.94 out of 5 average rating, 188 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!

Guest favourite
An overhead view showcases the expansive resort area, featuring a large swimming pool surrounded by lounge chairs. Nearby, a mini-golf course with vibrant green turf and multiple holes is visible. Tennis courts are located at the far side, surrounded by lush landscaping.
Apartment in Williamsburg
4.94 out of 5 average rating, 31 reviews

Family-friendly 1BR/1BA condo @ 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.

Guest favourite
Aerial view of a multi-unit building featuring Colonial-style architecture with blue siding and white trim. Lush greenery surrounds the property, adding to the garden-like landscaping, while the entrance is marked by walkways leading to each unit.
Apartment in Williamsburg
5 out of 5 average rating, 5 reviews

Comfortable 1BR Retreat in Williamsburg

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. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $250 refundable security deposit on hold at resort check-in. . Resort Fee at $7 per night. • Name on reservation must match photo ID at check-in.

Superhost
Condo in Williamsburg
5 out of 5 average rating, 6 reviews

Relax in Style: 1BR Condo w/ Balcony at Wyndham GG

Welcome to our beautiful 1BR Condo close to Historic Williamsburg! Everything needed for a memorable getaway to historic Williamsburg is right here. Take advantage of on-site recreation and endless amenities in a picturesque setting. The well-manicured lawns and pristine lakes make a lovely retreat after a day of adventuring in Colonial Williamsburg. Just three miles north of historic Williamsburg, we offer easy access to some of Williamsburg's most popular destinations.

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, 391 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
Guesthouse in Gloucester
5 out of 5 average rating, 162 reviews

Waterfront Escape • Pool, Dock & Creek View

A peaceful waterfront retreat tucked into 10 wooded acres above Bland Creek, perfect for long summer days and relaxed evenings. - Private screened-in porch with cooling creek breezes - Pool days, firepits under the stars, and quiet moments outdoors - Kayaks, a floating dock, fishing, and nature right outside your door - Immaculately clean and thoughtfully stocked for a stress-free stay - Quiet setting just minutes from downtown Gloucester

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, 233 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
The exterior of the building displays a welcoming layout, featuring multiple covered porches and classical architectural elements. Lush landscaping surrounds the entrance, with well-maintained shrubs and trees complementing the brick facade. The sky adds a soft evening glow to the scene.
Apartment in Williamsburg
4.83 out of 5 average rating, 29 reviews

Governor’s Green 1BR Dlx Condo w/ Full Kitchen

Everything needed for a memorable getaway to historic Williamsburg is right here. Take advantage of on-site recreation and endless amenities in a picturesque setting. The well-manicured lawns and pristine lakes make a lovely retreat after a day of adventuring in Colonial Williamsburg. This suite includes a King bed, and a Queen sleeper sofa in the main living area.

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, 176 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.

Guest favourite
Apartment in Williamsburg
4.9 out of 5 average rating, 20 reviews

1 Bedroom @ The Historic Powhatan 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
A spacious living area is showcased, featuring comfortable seating arrangements including a dark sofa and accent chairs. Natural light is welcomed through large glass doors leading to a balcony, with views of the lush surroundings. A fireplace and modern decor enhance the warm ambience.
Condo in Williamsburg
4.91 out of 5 average rating, 66 reviews

Cozy 2BR Condo in Williamsburg

Welcome to your getaway in Williamsburg, Virginia! Escape to our luxurious condo located in Kingmill resort on a pristine golf course in the heart of historic Williamsburg, Virginia. This beautifully furnished 2-bedroom, 2-bathroom retreat offers the perfect blend of relaxation and adventure for families and vacationers alike.

Guest favourite
A historic brick building is surrounded by vibrant flower beds featuring yellow, purple, and white pansies. Lush green grass leads up to the entrance, which is framed by neatly trimmed shrubs and trees, adding to the charm of the property.
Apartment in Williamsburg
5 out of 5 average rating, 8 reviews

Historic Powhatan - 2 Bedroom

Powhatan Resort provides accommodations with a restaurant, free private parking and a bar. The property is close to Colonial Williamsburg, Jamestown and 20 miles from Busch Gardens. Has an indoor and outdoor pool, hot tubs, tennis, mini-golf, restaurant, snack bar, game rooms.

Popular amenities for Williamsburg rentals with a pool

When is the best time to visit Williamsburg?

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Quick stats about vacation rentals with a pool in Williamsburg

  • Total vacation rentals

    Explore 1,690 vacation rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,640 verified reviews to help you choose

  • Family-friendly vacation rentals

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

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    960 properties have a dedicated workspace

  • Wifi availability

    1,690 of Williamsburg vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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