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Vacation rentals with a pool in Gloucester County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Gloucester County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Cobbs Creek
4.91 out of 5 average rating, 171 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, 205 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
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
4.98 out of 5 average rating, 164 reviews

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?

Top guest favorite
A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.
Barn in Cobbs Creek
4.95 out of 5 average rating, 129 reviews

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Guest favorite
The exterior of the farmhouse is surrounded by lush greenery, with a well-maintained lawn and blooming flowers. Spacious porches are featured on both levels, while large windows allow natural light to brighten the interior. The inviting entrance is highlighted by white railings and steps leading to the garden.
Home in Gloucester
5 out of 5 average rating, 22 reviews

Serenity Farm Equestrian Retreat in Historic VA

Relaxation at its finest for up to 16 guests at Serenity Farm in historic Gloucester County, VA. We are a working barn that overlooks groomed pastures and luscious gardens while offering views of a private equestrian estate. You will have full private access to this beautifully decorated farmhouse while enjoying the views, amenities, and proximity to history, golf, shopping, and theme parks! Historic Museums, Shopping, Restaurants, Local Breweries, and Art Galleries are only minutes away!

Top guest favorite
A spacious living area is furnished with comfortable sofas and a coffee table, surrounded by natural light from the large windows. The open layout transitions into a modern kitchen with white cabinetry and stainless-steel appliances, enhancing the welcoming atmosphere for gatherings.
Home in Hartfield
5 out of 5 average rating, 45 reviews

Maddie's Place

Relax with the whole family or a group of friends at this newly constructed home in Piankatank Shores, a golf cart community on the piankatank river. Plenty of space for 8 and a porta-crib available. Garage features a bar, big screen smart tv, a poker table, dart board & pool table. Relax on one of the local beaches. Plenty of parking for multiple vehicles and a boat. 12 mi to Urbanna, 1 Mi to the piakatank river golf club/steamboat restaurant. golf groups MUST BE 21 years old to book!

Superhost
A vibrant sunset casts a warm glow over the water, with rich hues of orange, pink, and purple reflected in the calm surface. A dock extends into the scene, framed by grassy edges, contributing to the serene atmosphere along the river.
Vacation home in Gloucester County
4.8 out of 5 average rating, 56 reviews

Waterfront 4 bedroom home with marina facilities

Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

Superhost
Home in Williamsburg
4.78 out of 5 average rating, 18 reviews

Our Home Away from Home

King’s Creek offers the charm of a village with the enjoyment of up-scale vacationing. Within the gated community, the fun begins with many on-site amenities including multiple swimming pools including the year-round indoor aquatic center, jetted pools, saunas, large workout room, tennis courts, playgrounds, jogging trail, barbecue grills, and basketball court and picnic areas that dot the rolling hills of woodlands blending with beautiful landscaping.

Top guest favorite
Home in Deltaville
5 out of 5 average rating, 44 reviews

Deltaville Serene Riverfront Getaway | 4BR

Escape to comfort, nature, and adventure! 🌅 This spacious 4-bedroom, 2.5-bath home is your perfect riverside retreat — offering the ideal blend of relaxation and outdoor fun. Wake up to breathtaking river views, spend lazy afternoons by the private pool, or dive into adventure with kayaking and fishing just steps away. Whether you're planning a fun family getaway or a chill trip with friends, this peaceful stay promises unmatched tranquility. 🌿

Top guest favorite
Guesthouse in Gloucester
5 out of 5 average rating, 159 reviews

Waterfront Escape • Pool, Dock & Creek View

A peaceful waterfront retreat tucked into 10 wooded acres above Bland Creek, perfect for long summer days and relaxed evenings. - Private screened-in porch with cooling creek breezes - Pool days, firepits under the stars, and quiet moments outdoors - Kayaks, a floating dock, fishing, and nature right outside your door - Immaculately clean and thoughtfully stocked for a stress-free stay - Quiet setting just minutes from downtown Gloucester

Top guest favorite
A spacious bed is positioned against a softly lit wall, complemented by decorative pillows. A bedside table features a lamp, providing warm lighting, while a second lamp stands on the opposite side, enhancing the cozy ambiance. Natural light enters through a window with blinds.
Apartment in Gloucester
4.95 out of 5 average rating, 58 reviews

Eclectic and Cozy Apartment

Close to many historical sites; Williamsburg, Yorktown, and the Northern Neck. Located on the Middle Peninsula. Close to the Tri- Rivers... fun family filled atmosphere with festivals all year long. Fully furnished. You only need your clothes and food. Full kitchen with all amenities. Owners on premises. Large dogs that are friendly. Pool available, with family and friends in and out. Small Par 3 practice space. Nice, quiet neighborhood.

Guest favorite
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.

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