Vacation 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, 178 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!

4.99 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

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.

4.97 out of 5 average rating, 153 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.

A well-appointed sleeping area features a spacious bed with neutral bedding accented by a decorative brown throw. Two bedside lamps provide soft lighting, and framed art hangs above the headboard. A window dressed with curtains allows natural light, complementing the room's warm tones.

5 out of 5 average rating, 3 reviews

Chic and Cozy 1BR in Williamsburg!

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. • 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. • Name on reservation must match photo ID at check-in.

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, 379 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, 128 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, 222 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.

5 out of 5 average rating, 148 reviews

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.

Guesthouse in Gloucester

Creekside Guesthouse - Dock and Pool on 10 acres

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.

4.93 out of 5 average rating, 123 reviews

Home in Hampton

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!!!

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.

4.9 out of 5 average rating, 292 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.

4.97 out of 5 average rating, 152 reviews

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.

Guesthouse in Suffolk

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.

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.

4.85 out of 5 average rating, 169 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 136 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

4.84 out of 5 average rating, 56 reviews

An aerial view captures a spacious two-story house with a grey roof, bordered by manicured landscaping. A paved driveway leads to the front where a car is parked. Surrounding open space and trees create a serene, natural setting.

Home in Providence Forge

Beautiful country house with 5 bedrooms 4.5 baths

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

4.94 out of 5 average rating, 16 reviews

A cozy living area features a comfortable sofa and a dining table set for two. The kitchenette is equipped with a full-sized refrigerator and a small stove. A vase of flowers adds a subtle touch to the inviting space, while warm lighting enhances the ambiance.

Home in Williamsburg

Our Home Away from Home

4.92 out of 5 average rating, 117 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

4.98 out of 5 average rating, 163 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

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: Kayaks-Screened Porch-RELAX

4.85 out of 5 average rating, 105 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!

Condo rentals with a pool

An indoor swimming pool is showcased beneath a high, vaulted ceiling with wooden beams. Large arched windows allow natural light to fill the space, reflecting on the clear water. Surrounding the pool, several deck chairs are arranged for relaxation.

4.9 out of 5 average rating, 31 reviews

Charming 2BR Colonial Condo at Wyndham Kingsgate

An outdoor fire pit area is surrounded by a curved brick wall and multiple seating options. Wooden chairs are positioned for comfortable gathering around the flames, while soft lighting highlights the lush landscaping and nearby buildings under a dusky sky.

4.91 out of 5 average rating, 23 reviews

Patriots Place, one bedroom condo, cozy space

A serene pond is framed by tall, lush trees, with greenery surrounding the water's edge. A fountain creates gentle ripples in the pond, reflecting the clear blue sky and trees. The peaceful scene invites relaxation and contemplation.

4.82 out of 5 average rating, 11 reviews

1br Colonial in Williamsburg -Fun by Busch Gardens

An outdoor pool area is presented with a large circular swimming pool, surrounded by loungers and shaded by pergolas. The clubhouse, featuring a welcoming design, is visible in the background against a clear blue sky dotted with clouds.

4.97 out of 5 average rating, 30 reviews

Wyndham Governor's Green, 3 BR Deluxe

The exterior of a two-story building is showcased, featuring a combination of brick and siding. Windows with blue shutters line the front, and a well-maintained lawn with small shrubs is visible. Paved parking is available in front of the building.

4.84 out of 5 average rating, 25 reviews

Williamsburg Vacation Villages Resort 2BR, 2BA

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, 146 reviews

Club Wyndham Kingsgate One-Bedroom Condo

5 out of 5 average rating, 9 reviews

Greensprings Vacation Resort 4 Bdrm

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.

4.83 out of 5 average rating, 6 reviews

Wyndham Patriots Place | King Bed Studio

Other vacation rentals with a pool

A row of charming cottages is framed by lush greenery and colorful flowering bushes. Paved walkways lead to the entrances of the homes, where distinctive architectural details, including gabled roofs and decorative railings, are visible. A white goose is seen walking along the well-maintained grass.

5 out of 5 average rating, 4 reviews

Historic Powhatan Resort 2 Bdrm! Sleeps 6

4.92 out of 5 average rating, 59 reviews

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

5 out of 5 average rating, 8 reviews

Peaceful Escape | Fireplace + Pool & Kitchen

4.85 out of 5 average rating, 13 reviews

An indoor swimming pool is highlighted by natural wood paneling and a sloped ceiling. Large windows provide views of the outdoors, while a hot tub is situated nearby. Two green lounge chairs are positioned beside the pool, creating a relaxing environment.

Home in Hampton

Chesapeake Bay Retreat Waterfront Indoor Pool

A historic manor house with a distinctive brick facade stands amidst a lush green landscape. A circular driveway leads to the entrance, framed by well-manicured gardens and mature trees. The sky features soft clouds, adding a serene backdrop to this iconic structure.

4.89 out of 5 average rating, 19 reviews

Historic Charm & Modern Comfort at Hilton Powhatan

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, 5 reviews

2 bedroom at The Historic Powhatan Resort

An indoor pool is illuminated by bright overhead lights. The clear blue water reflects the light and surrounding windows. Lounge chairs are positioned along the edge of the pool, providing a space for relaxation. Large windows allow natural light to fill the area.

Villa in Williamsburg

4.81 out of 5 average rating, 31 reviews

Quiet Villa with Access to Amazing Amenities

The exterior of the historic Manor House is captured, showcasing a stately brick facade with multiple windows and a central entrance. Lush greenery surrounds the building, with manicured flower beds and pathways leading to the entrance, framed by trees in the background.