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

Home in Cobbs Creek

4.91 out of 5 average rating, 134 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

Guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 170 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

Condo in Virginia Beach

4.84 out of 5 average rating, 121 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

Guest favorite

Home in Cobbs Creek

4.98 out of 5 average rating, 150 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

Home in Phoebus

4.85 out of 5 average rating, 181 reviews

Waterfront home with heated pool available!

This lovely, spacious waterfront home is full of things to do. It is the perfect get away! Enjoy views of the Hampton River while you relax in the heated salt water pool! You may have up to eight guests with our 4 bedroom 3 bath home. Additional guests are $30 per person and an air mattress can be provided upon request. Pets are welcome for $45 per pet, you must notify ahead of time. You may also have the pool heated during your entire stay for only $250. (DO NOT TOUCH THE POOL PUMP PLEASE)

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 531 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Guest favorite

Rental unit in Virginia Beach

4.87 out of 5 average rating, 145 reviews

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

This studio condo is located at the north end of Virginia Beach's famous boardwalk, just steps to the beach with an Atlantic Ocean view. Walking distance to area attractions, restaurants, and shopping. Ideal for couples with access to the salt water pool, lawn on the beach with lounge chairs and tables, and a reserved parking space. If you are visiting for a quiet getaway or for an event, you will love the boutique feel in an ideal location of this clean, newly renovated condo

Guest favorite

Tiny home in Cape Charles

4.98 out of 5 average rating, 303 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Guest favorite

Condo in Virginia Beach

4.9 out of 5 average rating, 204 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Guest favorite

Cottage in Norfolk

4.97 out of 5 average rating, 231 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.

Guest favorite

Home in Virginia Beach

4.96 out of 5 average rating, 186 reviews

Salida del Sol, 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!

Guest favorite

Cottage in Chesapeake

4.95 out of 5 average rating, 131 reviews

The Cottage @ Captain Genes - Secluded Waterfront

Get away from the crowds! Private, secluded upscale waterfront cottage on ~5 acres; pool/hot tub feet from the back door (hot tub open year round). Waterview from most rooms. Direct Chesapeake Bay access on property via dock / kayak launch. ~15 mins to downtown. Fish/crab, kayak, screened porch views, relax by the pool, fire pit or hot tub with a drink. Bring your boat - marina ~4 mi away - put-in there & tie-up at our pier!