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 1,630 vacation rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 10,010 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,070 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    930 properties have a dedicated workspace

  • Wi-Fi availability

    1,630 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
4.94 out of 5 average rating, 199 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
Home in Cobbs Creek
4.91 out of 5 average rating, 176 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

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, 208 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
Home in Irvington
4.99 out of 5 average rating, 127 reviews

The Rosé Retreat: Pool-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Top guest favorite
A sparkling pool is framed by a protective fence, with a shaded area provided by a large umbrella. Comfortable seating in bright colors is visible nearby, complemented by lush greenery in the background and a house with large windows capturing the daylight.
Guesthouse in Barhamsville
4.9 out of 5 average rating, 195 reviews

Peaceful Retreat w/ Fire Pit & Spa Services

Country living at its best! Quiet...peaceful & very special place to relax, release, and rejuvenate. We are surrounded by beautiful wineries, which are all minutes away. Gorgeous views of nature and seasonal flowers. Separate from the main house, our guest suite offers awesome privacy & comfort. You will enjoy this very quiet, cozy, peaceful retreat. It is the perfect hideaway with the utmost charm. Board Certified Reflexologist on the premises is available for appointments. So AMAZING!

Guest favorite
A private hot tub is situated on a wooden deck surrounded by trees, offering a serene retreat. Sunlight filters through the branches, creating dappled shadows on the tub's surface. A wooden wall adds a rustic touch, featuring a decorative crab motif.
Home in Irvington
4.96 out of 5 average rating, 166 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.

Top guest favorite
Guesthouse in Gloucester
5 out of 5 average rating, 174 reviews

Summer Escape - Dock, Pool, Firepits, & 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 (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Just minutes from downtown Gloucester

Guest favorite
Condo in Williamsburg
4.92 out of 5 average rating, 136 reviews

Colonial Williamsburg Spacious 4 Bedroom Suite!

This Resort is located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. The resort’s distinguished manor house that was originally built in 1735 captures the true essence of its Colonial surroundings. Discover the nation’s history at one of Williamsburg’s history museums, monuments or battlefields. The Resort features an indoor & outdoor pool, tennis court, playground. All suites have full kitchens, living/dining rooms & sleeper sofa.

Superhost
A wooden cabin constructed from rich timber is showcased amidst a natural setting. The structure features large windows that allow for natural light and a welcoming porch with sturdy steps leading to the entryway.
Cabin in Williamsburg
4.79 out of 5 average rating, 100 reviews

Log Cabin - Williamsburg Pet-Friendly, Heated Pool

Pet-friendly log cabin with 2 rooms, A/C & heat, free Wi-Fi, and cable TV. Includes a queen bed, breakfast bar, mini-fridge, microwave, and ceiling fan. No bathroom inside, but just steps from our first-class, professionally cleaned bathhouse. No kitchen. Outside: charcoal grill, picnic table, and fire ring. $20 per pet per stay. Linens/pillows not included—bring your own or rent a set for $20. Enjoy our 85° heated pool, free game room, and playground.

Top guest favorite
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, 239 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.

Superhost
Home in Hampton
4.91 out of 5 average rating, 128 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
A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.
Apartment in Irvington
5 out of 5 average rating, 111 reviews

Pelican Place, Cozy Retreat | Pool | Walk to Tides

Unwind at this stylish apartment with view of Carters Creek and walking distance to the cutest little town and the iconic Tides Inn Resort. Take a refreshing dip in the pool, enjoy the charming outdoor shower, and star gaze under a blanket from the rooftop deck. Several outdoor spaces and large yard with whimsical touches. The perfect hideaway close to all the Northern Neck has to offer.

Popular amenities for Williamsburg rentals with a pool

When is the best time to visit Williamsburg?

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