
Holiday rentals with a pool in Gloucester County
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Top-rated rentals with a pool in Gloucester County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.
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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.
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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.
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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?
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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.
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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!
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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.”
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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
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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.
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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
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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
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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)
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Popular amenities for Gloucester County rentals with a pool
House rentals with a pool

Get away to the heart of Deltaville!
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Estates at King's Creek: 2-BR, 2 Baths, Sleeps 6
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Stand Alone 3 Bedroom Cottage
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Luxurious 3 Bedroom Estate
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Pool & Dock Access! Bohannon Cottage on the Bay
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Lovely 3 bed cottage sleeps 10
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Squeaky Shores on the York River
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Williamsburg, VA
Condo rentals with a pool

Kings Creek Plantation Williamsburg Timeshare
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Close to Theme Parks & Attractions!
NearbyCleanlinessAccuracy

Patrick Henry Square Resort | 2-bedroom Suite
LocationWalkabilityGetting around

King's Creek Plantation: 2-BR, 2.5 Baths, Sleeps 6
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Cozy 1 Bedroom Condo, Williamsburg VA

Patriots Place 2 Bedroom
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Williamsburg VA, Patrick Henry Square - 2 Bd - BG
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CW Patriots Place Resort | 1BR/1BA King Bed Suite
Other holiday rentals with a pool

250th Celebration Week! 1 Bedroom Lux Resort+Pool
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Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort
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Inn and Sandy Creek
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Our Home Away from Home
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PATRIOts Place 2 Bedroom
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Wyndham Kingsgate ** 1BR
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Williamsburg King's Creek Plantation 1BR, 1BA Unit
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Williamsburg: Patriot Place-1 Bedroom
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- Rentals with pools Virginia
- Rentals with pools United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chesapeake Bay
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Old Dominion University
- Regent University
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- Neptune's Park
- First Landing Beach
- The Mariners' Museum
- Nauticus
- Hampton University
- Town Point Park
- Virginia Zoological Park
- Virginia Living History Museum
- Cape Henry Light House
- Virginia Beach Convention Center





