Some info has been automatically translated. Show original language

Holiday 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.

1 of 1 pages1 / 1
Superhost
A bright living area is highlighted by two armchairs and a comfortable sofa. A wooden coffee table occupies the center, while an electric fireplace adds interest. A flat-screen TV is mounted on the wall, accompanied by framed artwork. Natural light filters through the window blinds.
Apartment in Williamsburg
5 out of 5 average rating, 5 reviews

Gorgeous 2 bedroom Townes at Kingscreek sleeps 4-6

The Townes at King’s Creek offers all the amenities of luxury townhome living in two- or four- bedroom designs. Each suite also includes a private sitting area for relaxing at the end of each day. With lots of room to spread out, these fully furnished townhomes sleep six and feature two full bathrooms, including a master bath with a garden tub, two bedrooms, bright sunroom, electric fireplace, wet bar, washer and dryer. The Townes swimming pool is a summertime favorite for our owners and guests.

LocationFamilyCondition

Top Guest favourite
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, 213 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.

LocationFamilyCleanliness

Guest favourite
A fire pit is filled with bright flames and glowing embers, set against a tranquil lakeside backdrop. The water reflects the warm colors of a sunset, while silhouettes of trees frame the scene, creating a serene atmosphere.
Home in Gloucester County
4.8 out of 5 average rating, 5 reviews

Pine Cove on the Severn

Pine Cove is a 13-acre retreat on its own peninsula on the Severn - a tributary of the Chesapeake Bay. Taking a half-mile driveway, you will find an oasis surrounded by three sides of water, with a private pool, commercial-grade outdoor kitchen, a small fishing pier, and a 245’ pier (Currently not usable). Excellent fishing, boating, kayaking, and swimming in the pool. 20 minutes from Williamsburg, Jamestown, Yorktown, Busch Gardens, and Water Country USA, with countless shops and restaurants.

LocationFamilyRiver

Top Guest favourite
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, 170 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?

LocationValueKitchen

Top Guest favourite
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, 135 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.

FamilyLocationHospitality

Guest favourite
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, 23 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!

LocationFamilyGetting around

Top Guest favourite
Home in Cobbs Creek
4.91 out of 5 average rating, 179 reviews

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

Welcome to The Cottage at Misti Cove, where the Piankatank River is just steps from your door. Wake to sunrise views from bed, paddle the river by kayak or paddleboard, and unwind in your private waterfront hot tub as evening settles over the water. Enjoy the peaceful setting of a small community along with a seasonal pool, beach, pier and tennis court. It’s a cozy waterfront escape with exceptional views, thoughtful comforts and plenty of ways to slow down and say, “Now this is the life.”

ValueLocationView

Top Guest favourite
Guesthouse in Gloucester
5 out of 5 average rating, 184 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

FamilyLocationAmenities

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.
Holiday home in Gloucester County
4.81 out of 5 average rating, 57 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.

LocationValueBackyard

Top Guest favourite
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, 50 reviews

Maddie's Place

Escape with family or friends to this charming golf cart community. Sleeps up to 8 guests, with a porta-crib available. Enjoy the garage game room, with three Smart TVs, a poker table, dart board, and pool table. Spend your days soaking up the sun at nearby public beaches or lounging by the private pool. - 1 mile from Piankatank River Golf Club - A short drive to Busch Gardens, colonial Williamsburg, Water country USA - 12 miles from the charming town of Urbanna

LocationValueLayout

Top Guest favourite
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, 64 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. No pets allowed

FamilyLocationWi-Fi

Superhost
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.
Condo in Williamsburg
4.73 out of 5 average rating, 144 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)

FamilyValueAmenities

Popular amenities for Gloucester County rentals with a pool

Destinations to explore