Holiday rentals with a pool in Williamsburg

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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.
Apartment in Williamsburg
4.94 out of 5 average rating, 187 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 indoor swimming pool is surrounded by large arched windows that allow natural light to fill the space. Comfortable lounge chairs are positioned along the pool's edge, offering a relaxing area to unwind.
Resort in Williamsburg
4.92 out of 5 average rating, 64 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 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.
Apartment in Williamsburg
5 out of 5 average rating, 4 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.

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.
Flat 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.

Superhost
A spacious bedroom is furnished in Colonial style, featuring a king bed with decorative pillows and an earth-toned duvet. A bedside table holds a lamp, while sheer curtains frame the window. The walls are painted in warm hues, enhancing the cozy ambiance.
Flat in Williamsburg
4.5 out of 5 average rating, 12 reviews

Suitable 1BR Near Top Attractions!

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.

Guest favourite
A spacious bed, adorned with crisp white linens and decorative pillows, occupies the center of the room. A wooden headboard adds warmth, while a bedside lamp offers soft lighting. Natural light filters through a large window, framed by patterned curtains.
Flat in Williamsburg
5 out of 5 average rating, 8 reviews

Chic Urban Living: 1BR in Kingsgate!

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.

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, 390 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
Guest house in Gloucester
5 out of 5 average rating, 157 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 image showcases a row of two-story condos with light-colored exteriors set against a vibrant green lawn. Neatly trimmed bushes and small trees add to the landscape, which is touched by sunshine and soft clouds, creating an inviting environment.
Flat in Williamsburg
4.9 out of 5 average rating, 299 reviews

Historic Powhatan Resort- 2 bedroom condo!

Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Sumptuous, spacious accommodations offer a private balcony, loft and hot tub. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

Top guest favourite
An aerial view depicts the guest suite, nestled among lush greenery, with a spacious swimming pool nearby. The main house, along with various outdoor amenities, is visible, showcasing well-maintained landscaping and open fields surrounding the property.
Guest house in Suffolk
4.96 out of 5 average rating, 163 reviews

Country Living Guest House (Upstairs/Downstairs)

This country living guest suite is conveniently positioned on Lone Star Lakes Park. It is located in a quiet, private drive. Prepare quality meals in the down-stairs fully equipped eat-in kitchen with built-in cabinets, spacious countertops, a full-sized fridge, an electric stove, and everything you need to feel at home. Just off the kitchen is a half-bath. NO PETS ALLOWED.

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.
Flat 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.
Flat
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.

Popular amenities for Williamsburg rentals with a pool

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Quick stats about holiday rentals with a pool in Williamsburg

  • Total holiday rentals

    Explore 1,690 holiday rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg holiday rentals start at € 25 per night before taxes and fees

  • Verified guest reviews

    Over 10,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,000 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    960 properties have a dedicated workspace

  • Wifi availability

    1,690 of Williamsburg holiday 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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