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Holiday rentals with a pool in James City County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in James City County

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
The outdoor pool area features a large, clear pool surrounded by a stone patio. Sun loungers are lined up neatly along the edges, with shaded seating areas in the background. The clubhouse is visible with its inviting architecture, under a bright sky scattered with clouds.
Condo in Williamsburg
4.88 out of 5 average rating, 17 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

Guest favourite
A row of two-story buildings showcases a mix of soft grey and white siding. Lush green lawns are bordered by well-manicured shrubbery, with vibrant trees adding color. The open sky above features scattered clouds, enhancing the sense of space around the structures.
Apartment in Williamsburg
4.93 out of 5 average rating, 101 reviews

*Historic Powhatan Resort- 2 bedroom

Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. The resort features a distinguished manor house that was originally built in 1735 and captures the true essence of its Colonial surroundings. Discover the nation’s history at one of Williamsburg’s history museums, monuments or battlefields, and immerse yourself in the city’s Colonial spirit.

Guest favourite
The historic manor house, built with classic red bricks, stands prominently against a backdrop of lush greenery. A pathway leads through vibrant flower beds to the entrance, showcasing the charm of Colonial architecture under a clear blue sky.
Apartment in Williamsburg
4.98 out of 5 average rating, 41 reviews

3 Bedroom Suite in Historic Williamsburg!

Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. Bring the whole family to this great place with lots of room for fun • 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 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, 112 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.

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
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.

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