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.

4.94 out of 5 average rating, 185 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!

4.91 out of 5 average rating, 170 reviews

Home in Cobbs Creek

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

4.99 out of 5 average rating, 205 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.

4.98 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?

4.91 out of 5 average rating, 206 reviews

A serene waterfront view features two kayaks resting on the grass under tall trees. A wooden dock extends into the water, surrounded by lush greenery and a clear blue sky. The area offers a peaceful setting for outdoor activities.

Farm stay in Cardinal

Wtrfrnt aptmnt w/pool/dock on private farm

Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

4.97 out of 5 average rating, 158 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.

Apartment in Williamsburg

A spacious bed, adorned with crisp white linens and decorative pillows, occupies the center of the room. A wooden headboard adds warmth, while a bedside lamp offers soft lighting. Natural light filters through a large window, framed by patterned curtains.

5 out of 5 average rating, 8 reviews

Chic Urban Living: 1BR in Kingsgate!

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.

5 out of 5 average rating, 157 reviews

Guesthouse in Gloucester

Waterfront, Pool, Dock & Firepits-The Bluebird

Perched above Bland Creek on 10 acres, The Bluebird Guesthouse is a retreat immersed in nature. Guests consistently praise its immaculate cleanliness, screened-in porch with creek views, and thoughtful touches, such as a well-stocked kitchen and fresh cookies. Kayak, fish, enjoy firepit evenings, or relax and listen to the birds. When it’s time to explore, eclectic shopping and dining in historic downtown Gloucester are just minutes away, with Williamsburg an easy drive.

4.91 out of 5 average rating, 129 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.

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, 388 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.

5 out of 5 average rating, 229 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.

Apartment in Williamsburg

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, 299 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.

Popular amenities for Williamsburg rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 147 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

4.85 out of 5 average rating, 66 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, 26 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

4.93 out of 5 average rating, 121 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, 124 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, 107 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, 155 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

Deltaville Serene Riverfront Getaway | 4BR

Condo rentals with a pool

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 indoor swimming pool is surrounded by a spacious area featuring large windows that allow natural light to fill the space. Light blue walls and a high ceiling create an airy atmosphere. Comfortable seating is positioned along the side of the pool.

5 out of 5 average rating, 7 reviews

Charming 3BR Colonial Condo at Wyndham Kingsgate

A serene resort view is presented, featuring three white multi-story buildings by a calm pond. The clear water reflects the structures and a fountain creates gentle ripples, enhancing the tranquil atmosphere of the surrounding greenery.

4.95 out of 5 average rating, 19 reviews

1 Bdrm Condo in Williamsburg, VA

An indoor swimming pool area is featured, with a clear blue water surface reflecting light. Tall glass walls allow natural light to illuminate the space, creating a bright atmosphere. Lounge chairs are neatly arranged along the poolside, offering relaxation options for guests.

4.83 out of 5 average rating, 6 reviews

Charming 1BR Colonial Condo at Wyndham Kingsgate

A two-story building is shown, featuring a combination of white siding and dark shingles. The front porch is framed by white steps and railings. Well-maintained landscaping, including shrubs and trees, enhances the overall appearance in a bright, open setting.

5 out of 5 average rating, 8 reviews

Wyndham Patriots' Place one bedroom

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.

4.83 out of 5 average rating, 12 reviews

1br Colonial in Williamsburg -Fun by Busch Gardens

A well-appointed guest room features a spacious bed with a light-colored coverlet, complemented by two bedside lamps on wooden tables. A large window is adorned with patterned curtains, allowing natural light to fill the space. A wooden dresser and a wall-mounted television are included.

4.78 out of 5 average rating, 18 reviews

Patriots Place 2 Bedroom

An outdoor swimming pool is framed by a spacious deck, featuring lounge chairs and shaded areas for relaxation. Surrounding buildings consist of two-story accommodations, with trees in the background, and clear skies overhead creating a bright, open atmosphere.

4.91 out of 5 average rating, 11 reviews

Wyndham Kingsgate (3 BD LO)

Other holiday rentals with a pool

4.92 out of 5 average rating, 63 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

Hotel room in Williamsburg

4.89 out of 5 average rating, 19 reviews

Spacious 4 BD Suite near Colonial Williamsburg

4.84 out of 5 average rating, 19 reviews

Home in Hampton

Chesapeake Bay Retreat Waterfront Indoor Pool

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

A spacious resort is displayed beside a serene lake, featuring a central pool area surrounded by lounge chairs. A water fountain creates a gentle spray in the foreground, while well-maintained lawns lead to the buildings that house various amenities.

4.96 out of 5 average rating, 27 reviews

Relax in Style: 2BR Condo w/ Balcony at CW Governo

Apartment in Williamsburg

A row of multi-story buildings is set against a bright blue sky with fluffy clouds. Lush greenery and neatly trimmed bushes frame the entrance, while small flowering trees add color to the landscaping, creating a welcoming exterior for guests.

5 out of 5 average rating, 24 reviews

4BR Williamsburg Retreat – Pool, Tennis & BBQ

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.

4.87 out of 5 average rating, 15 reviews

Relax in Style: 1BR Condo w/ Balcony at Wyndham GG

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.