Holiday rentals with a pool in Williamsburg

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.

4.93 out of 5 average rating, 182 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!

4.98 out of 5 average rating, 164 reviews

A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.

Home in Cobbs Creek

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

The exterior of a charming three-story building is showcased, featuring red brick walls and a steeply pitched roof. Large windows with white railings overlook a landscaped courtyard with fountains and blooming trees, creating a welcoming ambiance surrounded by greenery.

4.96 out of 5 average rating, 47 reviews

Marriott's Manor Club Ford's Colony 2BD Villa Slee

Discover for yourself where the United States began. Surrounding your resort are some of the most iconic spots in our nation's glorious past, including Yorktown and the amazing Jamestown Settlement replica, where costumed historical interpreters describe and demonstrate daily life in pre-Revolutionary War America. Williamsburg also offers fun modern-day attractions for the whole family. Thrill to fantastic rides at the Busch Gardens Williamsburg theme park, or cool down at Water Country USA.

4.97 out of 5 average rating, 155 reviews

Two classic white Adirondack chairs are positioned on a grassy bank overlooking the calm water of the Rappahannock River, framed by gently swaying trees. The sky displays a soft transition of colors as the sun sets, creating a serene and inviting view.

Home in Locust Hill

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Farm stay in Williamsburg

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.

4.97 out of 5 average rating, 381 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.

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.

4.75 out of 5 average rating, 130 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)

5 out of 5 average rating, 224 reviews

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

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 house in Gloucester

A serene outdoor seating area is nestled among colorful autumn leaves, with four adirondack chairs arranged around a wooden platform. The setting sun casts a warm glow over the peaceful view of Bland Creek and the marsh, enhancing the natural beauty of the landscape.

5 out of 5 average rating, 150 reviews

The Bluebird — Waterfront, Pool, Dock & Firepits

With stunning views overlooking Bland Creek, this guesthouse is the perfect place to unwind or start your adventure. This two-bedroom apartment is nestled high in the treetops, perfectly situated on 10 acres of wooded and coastal beauty. When the time comes to explore, guests are only minutes away from eclectic shopping and dining in historic downtown Gloucester, with Williamsburg and Richmond an easy 45 minutes away.

Serviced apartment in Williamsburg

The historic manor house, built in 1735, features a robust brick exterior with large windows and a slate roof. Lush green gardens and flower beds surround the structure, complemented by a winding brick pathway leading to the entrance.

5 out of 5 average rating, 10 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..

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.

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.

Serviced apartment in Williamsburg

A row of well-maintained townhouses is situated in a green landscape. Lush bushes and manicured lawns frame the buildings. A flowering tree adds color to the scene under a bright blue sky with scattered clouds.

4.91 out of 5 average rating, 44 reviews

2 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.

4.89 out of 5 average rating, 47 reviews

A spacious studio room showcases a comfortable king-size bed, complemented by a cozy sofa and a side chair. A dining table with two chairs is positioned near large windows, allowing natural light to illuminate the light-colored decor and art pieces adorning the walls.

Villa in Williamsburg

Resort, Studio at Marriott's Manor Club

At Marriott's Manor Club at Ford's Colony, you'll find a historical Williamsburg hideaway that's dedicated to choice, whether you visit renowned theme parks, revisit living history or relax at this beautiful, exclusive retreat. Our Studio (Hotel style guest room) has a comfortable king size bed and a Queen sized sofa.

Popular amenities for Williamsburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 139 reviews

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

Wooded Wonderland Miniature Golf Hot tub Pool

5 out of 5 average rating, 25 reviews

A spacious waterfront home is depicted at sunset, with large windows reflecting warm light. Surrounding greenery and floral plantings lead to a patio area featuring outdoor seating. A saltwater pool is visible, along with shaded lounge areas under blue umbrellas.

Home in White Stone

Waterfront panoramic point with pool

4.99 out of 5 average rating, 203 reviews

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

York River Vacation Home

4.92 out of 5 average rating, 118 reviews

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

Home in Norfolk

Gorgeous Vacation House

4.99 out of 5 average rating, 121 reviews

The entrance to The Rosé Retreat features a welcoming porch with multiple chairs arranged for relaxation. Arching glass doors provide a view into the inviting interior, framed by decorative wreaths that add a touch of seasonal charm. Lush green foliage surrounds the exterior.

Home in Irvington

The Rosé Retreat: Fireplace-Screened Porch-RELAX

4.85 out of 5 average rating, 106 reviews

A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.

Home in Suffolk

Perfect Getaway!

4.96 out of 5 average rating, 152 reviews

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

Magical wooded cottage pool +priv hottub walk2town

5 out of 5 average rating, 43 reviews

A spacious living area features large windows that offer views of the river and natural light. Comfortable seating is arranged around a central coffee table, with a flat-screen TV mounted on the wall. Light-colored curtains complement the decor.

Home in Deltaville

Waterfront 4BR | Pool & Peaceful Deltaville Views

Apartment rentals with a pool

The restored Manor House, dating back to 1735, features a classic brick facade with a symmetrical arrangement of windows and a central door. A manicured lawn with neatly arranged plants and a brick pathway leads to the entrance, surrounded by lush greenery and trees.

4.83 out of 5 average rating, 6 reviews

The Historic Powhatan, 2br suite, Friday check-in

An outdoor swimming pool is surrounded by lounge chairs under green umbrellas. Tall trees provide shade in the background, enhancing the serene atmosphere. The pool area is maintained and invites relaxation in the sunny environment.

4.75 out of 5 average rating, 4 reviews

Wyndham Patriots Place | 1BR/1BA King Bed Suite

An indoor pool area is highlighted by a high, translucent roof that allows natural light to fill the space. Lounge chairs are arranged around the pool, creating a relaxing environment. The water reflects the surroundings, enhancing the open and airy atmosphere.

5 out of 5 average rating, 4 reviews

Patrick Henry Square Resort | 2BR Suite

An aerial view of the resort highlights the outdoor amenities, including a large swimming pool surrounded by lounge chairs, a miniature golf course with vibrant green putting greens, and tennis courts in the background. Lush landscaping enhances the inviting atmosphere.

5 out of 5 average rating, 3 reviews

Williamsburg K, VA,2-Bdrm Dlx #3

An indoor pool area is framed by tall windows that allow natural light to fill the space. Lounge chairs line the perimeter of the pool, which is surrounded by a light-colored stone floor. High ceilings with white beams create an airy atmosphere.

4.5 out of 5 average rating, 6 reviews

Williamsburg Kingsgate one bedroom

A sweeping view of a lush green golf course is presented, featuring gently curving pathways and sand traps. Tall trees provide shade along the course, and a few golfers are visible in the distance, contributing to the serene landscape.

4.95 out of 5 average rating, 80 reviews

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

A circular brick fire pit area is surrounded by multiple wooden chairs, set on a wooden deck. The glow of the fire contrasts with a dusk sky, creating a calming environment. Nearby, buildings are visible, framed by lush trees and shrubbery.

4.86 out of 5 average rating, 7 reviews

Wyndham Patriots Place | King Bed Studio

A circular brick fire pit area is surrounded by wooden Adirondack chairs, providing a cozy space for gathering. The scene is set against a backdrop of trees and buildings, with the sky transitioning to twilight hues, enhancing the inviting atmosphere.

5 out of 5 average rating, 5 reviews

Wyndham Patriots Place | King Bed Studio

Other holiday rentals with a pool

The front view of the Registration Building and clubhouse reveals a welcoming facade with a central entrance framed by large planters. Lush green lawns and symmetrical landscaping enhance the accessibility of the structure, which features a second-story balcony overlooking the outdoor area.

5 out of 5 average rating, 3 reviews

Amazing 2 bdrm at The Colonies

Hotel room in Williamsburg

Spacious 4 BD Suite near Colonial Williamsburg

A charming white house is surrounded by a lush green lawn, featuring vibrant flowering plants along the walkway. A wooden fence encloses the property, and large trees provide shade, contrasting the blue sky and soft clouds above.

5 out of 5 average rating, 6 reviews

2 bedroom at The Historic Powhatan Resort

The exterior of a grand building is highlighted by large white columns and an elegant entrance. Surrounding trees display vibrant autumn foliage, enhancing the welcoming ambiance. A symmetrical design features multiple windows and a prominent rooftop, contributing to the overall sophisticated aesthetic.

4.72 out of 5 average rating, 25 reviews

Williamsburg Plantation: 2-BR, Sleep 6, Kitchen

Serviced apartment in Williamsburg

A row of two-story townhouses is showcased against a clear blue sky. Lush green lawns and manicured shrubs line the pathway leading to the homes. Trees display vibrant foliage, enhancing the inviting exterior of the residences.

4.92 out of 5 average rating, 74 reviews

*Historic Powhatan Resort- 4 bedroom sleeps 12

Two colonial-style buildings with light-colored exteriors are set by a calm pond. Balconies overlook the water, and a fountain creates a serene atmosphere. Lush greenery surrounds the buildings, providing a pleasant outdoor setting.

4.88 out of 5 average rating, 43 reviews

Kingsgate Resort 2 Bedroom

Several three-story buildings are depicted along the water's edge, reflecting on the calm surface of the pond. A fountain can be seen in the foreground, creating gentle ripples in the water. Lush greenery surrounds the buildings, enhancing the serene ambiance.

4.59 out of 5 average rating, 148 reviews

Club Wyndham Kingsgate One-Bedroom Condo