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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, 189 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 favourite
Guesthouse in Gloucester
5 out of 5 average rating, 164 reviews

Summer Waterfront • Dock, Pool, & Kayaks

A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use - Firepit evenings, and true outdoor living - Dock, kayaks, fishing, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Peaceful setting just minutes from downtown Gloucester

Guest favourite
Condo in Williamsburg
4.86 out of 5 average rating, 7 reviews

WaterVue at Kingsmill

Welcome to WaterVue; our Kingsmill, home-away-from-home in historic Williamsburg, Virginia. Be one of the first to stay in spacious style with completely updated amenities. You will be treated to fresh, clean accommodations, soft linens; everything you need is available for your stay. Sit and relax on any of the balconies that overlook Wareham's Pond. Catch wildlife passing by or hear the memorable train whistle from Busch Gardens next door. Close your eyes and experience serenity and peace.

Guest favourite
A group of colonial soldiers in traditional attire, including red coats and white trousers, is seen marching in a smoky outdoor setting. Some hold flutes, while a lead soldier plays a brass instrument, creating a historical reenactment atmosphere.
Townhouse in Williamsburg
5 out of 5 average rating, 11 reviews

3BDR TH near history, relaxation and fun! Sleeps 8

If you're looking to take your family on a vacation that will be not only loads of fun but filled with plenty of opportunities to teach them about U.S. history w/o them feeling like they're learning anything, you need to visit Williamsburg, VA. You're going to want a great place to stay that has everything any vacationer could ever want, that place is The Historic Powhatan Resort. Here you'll find all the comforts of home, as well as a beautiful resort that is ideal for guests of all ages.

Guest favourite
A charming single-story cottage is set against a green lawn, featuring a porch with a covered seating area. Inside, a fully equipped kitchen with modern appliances is visible, along with a dining table. Cozy living areas and a private bedroom are adorned in soft yellow tones.
Cottage in Williamsburg
4.75 out of 5 average rating, 44 reviews

Cottage

Pet-friendly cottage with A/C, Wi-Fi, and full kitchen. Sleeps up to 6. Bedroom has luxury queen bed, linens, and 32" TV. Living room features 50" TV and double futon (futon linens not included but available to rent). Kitchen includes stove, fridge, microwave, and coffee maker. Outdoor space has fire ring, grill, picnic table, and porch swing. $30 per pet per stay. Enjoy access to our 85° heated pool, free game room, playground, basketball, and walking path to the lake.

Guest favourite
A large outdoor pool is featured, surrounded by a spacious deck with numerous lounge chairs and umbrella-covered tables. Nearby, various resort buildings are visible, set against a clear blue sky. The pool area is designed for relaxation and leisure.
Condo in Williamsburg
5 out of 5 average rating, 14 reviews

Wyndham Kingsgate (3 BD LO)

The Wyndham Kingsgate resort is less than a mile away from Historic Williamsburg and seven miles from Busch Gardens. The resort has a friendly staff that is available 24/7. The unit we have available for rent is a spacious 3 bedroom 3 bath lock off with a separate living and dining rooms, private balconies, washer/dryer and a full kitchen. . My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

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
4.75 out of 5 average rating, 135 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 favourite
Condo in Williamsburg
5 out of 5 average rating, 26 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.

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
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, 183 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
A three-story building displays a mix of brick and siding materials, framed by well-maintained green lawns and landscaping. Large windows with green shutters and white trim offer a welcoming appearance, complemented by a prominent entrance with columns and a covered porch area.
Apartment in Williamsburg
4.73 out of 5 average rating, 22 reviews

2 Bedroom Greensprings Vacation Resort (Sleeps 6)

Located in historic Williamsburg, Virginia, Greensprings Vacation Resort features the essential amenities you need for an unforgettable vacation. • 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
4.92 out of 5 average rating, 71 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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