Vacation rentals with a pool in Williamsburg

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Top-rated rentals with a pool in Williamsburg

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

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Guest favorite

A refreshing outdoor pool is surrounded by a spacious deck. Lounge chairs are positioned around the pool, set against a backdrop of lush greenery and distant buildings. Clear blue skies and gentle clouds enhance the serene atmosphere of the area.

Home in Cobbs Creek

4.9 out of 5 average rating, 149 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

Superhost

A spacious home is set among lush greenery, featuring large windows that allow natural light to flood the interior. A private, inviting saltwater pool is surrounded by a deck, with steps leading up to the house and shaded areas provided by patio umbrellas.

Home in Lancaster

4.63 out of 5 average rating, 19 reviews

Peaceful bay retreat. Hot tub,water views,fire pit

Peaceful get away on the sandy shores of the Corrotoman "Rivah" full of water activities. Fast WiFi, private saltwater pool(open May-Sept), kayaks, canoe, private sand beach, hot tub, full kitchen, pool table, firepit, deck with grill, outdoor dining tables. Deep water dock bring or rent a boat. Yankee Point Marina offers boat rentals, live music & restaurant w/in walking distance! Ride free ferry into Kilmarnock for shopping, restaurants & wineries. Kayak w/dolphins, watch Rock fish from dock

Top guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 178 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

The pool area is showcased with a clear blue water feature and adjacent Jacuzzi. Surrounding lounge furniture and a nearby seating arrangement provide space for relaxation. The backdrop features a low, stone wall and buildings with a warm color palette, enhancing the community atmosphere.

Condo in Sandbridge

4.87 out of 5 average rating, 233 reviews

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Superhost

An aerial view captures the expansive backyard setting, featuring a large blue swimming pool and a spillover hot tub. The area is surrounded by well-maintained greenery and palm trees, with outdoor furniture arranged for relaxation. Spacious outdoor areas are visible, complementing the nearby structures.

Home in Virginia Beach

4.83 out of 5 average rating, 42 reviews

Luxury Home, 50' pool, hot tub, grill & pool house

Reunion Paradise! Upscale 5300 SQ FT PLUS Hot Tub, Sauna, Steam Shower, 50' Pool. Quiet & safe when you want to walk, bike or go for a jog at any time. This home is furnished with Ethen Allan tables & chairs, Restoration Hardware and Pottery Barn Bedrooms. Plenty of room in the backyard for a great family reunion. Enough grass space for put up a volleyball. 50' pool, 8 foot deep end, 3.5' shallow end (over 1/2 the pool) Spill over hot tub to enjoy watching the stars or family in the pool.

Guest favorite

A saltwater pool is bordered by white lounge chairs, offering a view of the Atlantic Ocean in the distance. A deck with beach umbrellas is visible beyond the pool, while the sunny sky features a few scattered clouds.

Condo in Virginia Beach

4.89 out of 5 average rating, 210 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

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?

Superhost

Vacation home in Sandbridge

4.89 out of 5 average rating, 38 reviews

VB Paradise / Private Pool, Hot Tub

Outdoor living is king at “A Secret Spot”, a lovely cottage located at the north end of Sandbridge. Offering a beautiful outdoor pool area, fenced yard for children, covered hot tub, and plenty of decks and space to spread out or gather together! Under the house offers an outdoor living room with seating, a ping pong table, and picnic table. Imagine steamed crabs and drinks while relaxing with family by the pool. ! Inside there are more games for everyone to enjoy.

Guest favorite

A spacious backyard features a saltwater inground pool surrounded by manicured grass. A two-level deck is visible with patio furniture, offering comfortable seating options. The exterior of the two-story house is seen in the background, under a partly cloudy sky.

Home in Suffolk

4.84 out of 5 average rating, 88 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Top guest favorite

A lagoon-style saltwater pool is framed by a spacious deck, featuring multiple lounge chairs. Beyond the pool, serene water views are observed, and lush greenery adds a natural touch to the setting.

Home in Sandbridge

4.95 out of 5 average rating, 22 reviews

Sandbridge- Great Escape Saltwater Pool &Boat Ramp

Stunning panoramic water views! Enjoy this classic cozy coastal home with an open floor plan, fully stocked kitchen & lagoon style saltwater pool. Lots of covered deck space, including a screened-in porch for relaxing after a day in the sun. 3 bedrooms, 2 full baths, an enclosed outdoor shower. Located on quiet neighborhood street with easy walk to the beach. Bring your water toys for this is a waterfront home with private boat ramp and pool. Sunday check-in.

Top guest favorite

A private saltwater pool is depicted, surrounded by a spacious patio area. The pool's clear blue water is inviting, with a ladder providing easy access. Lush greenery and a white fence frame the background, enhancing the serene ambiance near the Chesapeake Bay.

Cottage in Norfolk

4.97 out of 5 average rating, 241 reviews

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Top guest favorite

An outdoor swimming pool is surrounded by a spacious deck area. Several white lounge chairs are arranged neatly along the poolside, providing spots for relaxation. Shade umbrellas are positioned at intervals, enhancing the leisure space. The pool is bordered by landscaped greenery and residential buildings.

Home in Virginia Beach

4.96 out of 5 average rating, 194 reviews

Sunrise, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!