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, 148 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, 177 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, 21 reviews

Deltaville Serene Riverfront Getaway | 4BR

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!

Guest favorite

Home in Cobbs Creek

4.98 out of 5 average rating, 152 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

4.95 out of 5 average rating, 112 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.

Superhost

Vacation home in Gloucester County

4.79 out of 5 average rating, 42 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

Apartment in Williamsburg

4.75 out of 5 average rating, 4 reviews

2 bdrm in resort w activities

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. Situated just one mile from Williamsburg's historic area, you'll experience history all around you. Enjoy a little retail therapy at charming local shops or the Williamsburg Outlet Mall.

Superhost

Apartment in Williamsburg

4.63 out of 5 average rating, 8 reviews

One bedroom condo - Williamsburg

Perfect place to relax and unwind while being minutes away from Historic Williamsburg, Busch Gardens Williamsburg and Pirate's Cove Adventure Golf, College of William and Mary and Williamsburg Premium Outlets. This property offers fabulous amenities including Children's Playground, Fire Pit, Hot Tub (Outdoor), Swimming Pool (Outdoor) Swimming Pool (Outdoor), Barbecue Area and Basketball Courts. Lots of things for you and the family to enjoy.

Top guest favorite

Apartment in Gloucester

4.93 out of 5 average rating, 43 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

Farm stay in Gloucester

5 out of 5 average rating, 28 reviews

Colonial Farmhouse on 14 serene acres w/ huge pool

"Patriot Plantation" circa 1750's is perfect for family gatherings! A seasonal pool/party barn is adjacent to the 20x40 inground pool (pool open June-August). We invite you to pick seasonal herbs, fruit and nuts: blackberries, pawpaw, black walnut and pecans. Relax and unwind on our 14 tranquil acres! Close to amenities: 10 minutes to Walmart; 45 minutes to Colonial Williamsburg/historic triangle; and 20-30 minutes to local wineries.

Superhost

Guesthouse in Gloucester

4.93 out of 5 average rating, 98 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.

Guest favorite

Cottage in Cardinal

4.95 out of 5 average rating, 123 reviews

Haddie James House - A Coastal Va AirBnB

Escape to the East River in Mathews County, Virginia in our cozy coastal cottage nestled in the back of our 3.5 acres of waterfront property. Haddie James House is a quick 15 minutes to downtown Mathews and 20 minutes to Gloucester Courthouse. Enjoy beautiful sunrises and sunsets.

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What guests are saying

Inn at Sandy Creek

5 out of 5 average rating, 23 reviews8 months ago

First I think Donna 100% underrated the place. My Grandson loved all the animals that are free to see and pet. She evens provides feed for the animals. The Pool was nice and private and clean. The loft was clean and stocked with everything you will need for a stay. We used the kitchen to cook breakfast, lunch and dinner. Had enough utensils for all. She undersold the grilling. Had a large gas grill with a flat grill attached. Charcoal grill and a gas smoker by pool. You have a private entrance from the garage and she has plenty of tools for a quick fix. Donna was great and every time see saw you she checked to make sure everything was ok. She even put snacks and drinks in fridge for us. She even paid attention that we had a child and got juice for him. DoorDash does deliver to house if you don’t feel like cooking.Patriot Grill and Sweet Tooth was our favorite. Wish I got a flight of beers at the Brewery because the one I got was just ok. Donna does adopt animals so we got so vegetable

Loft in James Store

What guests are saying

King’s Creek Resort. Next to Country Water 2BR/2BA

5 out of 5 average rating, 4 reviews8 months ago

Super amazing host! they even called the day of check in and check out! They went above and beyond to accommodate me. place was clean and spacious! probably one of the larger resorts we have stayed at. The spare sun room is truly lime a third bedroom. There are multiple pools and the indoor cotton is amazing! Great fitness center and walking distant to amusement parks! Perfect find!

Apartment in Williamsburg

What guests are saying

Williamsburg King's Creek Plantation 1BR, 1BA Unit

5 out of 5 average rating, 3 reviews14 months ago

We used this space while our home was being worked on, do it was more of a “staycation” and did not use all of the amenities. The space was clean and newly renovated, so we were pleased with how nice things were. I highly recommend it for people visiting the Williamsburg area. Great location to Busch Gardens, W&M, etc. The only negative is that it is a time share, and they don’t take no for an answer.

Apartment in Williamsburg

What guests are saying

Wyndham Patriot's Place 1 Bedroom Condo

5 out of 5 average rating, 6 reviews9 months ago

Beautiful ground floor condo close to everything in Williamsburg. Condo is nicely equipped for a short to medium stay. Bed is comfortable and shower has great water pressure and amenities. Pool is a short walk away, with pool towels provided. Wyndham did call me and ask me to do a timeshare presentation, but they were cordial and didn’t pushed when I declined. I would absolutely stay here again if I’m in the Williamsburg area.

Apartment in Williamsburg

What guests are saying

Wtrfrnt aptmnt w/pool/dock on private farm

4.89 out of 5 average rating, 156 reviews1 week ago

I had to cancel unfortunately because of the weather emergency Arkansas was going through. I gave Shelli five stars because of her graciousness and kindness when I to cancel. I will definitely be booking her place when I get to take my trip next year! Thanks Shelli!

Farm stay in Cardinal

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