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

4.9 out of 5 average rating, 163 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

Home in Gloucester Point

4.99 out of 5 average rating, 200 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.

Guest favorite

Home in Deltaville

5 out of 5 average rating, 40 reviews

Waterfront 4BR | Pool & Peaceful Deltaville Views

This spacious 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, relaxation, and outdoor adventure. Wake up to stunning river views, and spend your days lounging by the private pool, kayaking, fishing, or exploring the serene surroundings. Whether you're looking for a fun-filled family vacation, or a friends' getaway, this serene stay provides unmatched tranquility Book now for spring & summer, and experience warm breezes, golden sunsets, and the ultimate waterfront experience!

Top guest favorite

Home in Cobbs Creek

4.98 out of 5 average rating, 162 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?

Guest favorite

Barn in Cobbs Creek

4.94 out of 5 average rating, 126 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

Home in Gloucester

5 out of 5 average rating, 20 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!

Guest favorite

Farm stay in Cardinal

4.91 out of 5 average rating, 193 reviews

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.

Top guest favorite

Home in Hartfield

5 out of 5 average rating, 41 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

Apartment in Williamsburg

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.

Top guest favorite

Apartment in Gloucester

4.94 out of 5 average rating, 52 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.

Top guest favorite

Guesthouse in Gloucester

5 out of 5 average rating, 143 reviews

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.

Superhost

Condo in Williamsburg

4.6 out of 5 average rating, 20 reviews

Wyndham Patriots Place | King Bed Studio

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. Wyndham Patriots Place | King Bed Studio • Size: 380 - 380 • Kitchen: Mini • Baths: 1 • Accommodates: 2 Guests • Beds: King Bed - 1