Waterfront vacation rentals in Willoughby Bay

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Willoughby Bay

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene view of a saltwater pool reflects the clear blue sky, with a shaded seating area nearby. In the background, a private dock extends into the water, lined by greenery and offering a peaceful ambiance.

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.

Top guest favorite

Cottage in Norfolk

5 out of 5 average rating, 270 reviews

Beautiful Cottage Waterfront Near Downtown Norfolk

A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

Superhost

An aerial view captures the marina with multiple boat slips along the calm water, framed by a well-maintained boardwalk. The nearby building features a green roof and outdoor seating areas, complementing the serene waterfront setting under a clear blue sky.

Condo in Williamsburg

4.94 out of 5 average rating, 124 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Top guest favorite

The exterior of a two-story home is showcased, featuring natural wooden siding and two private balconies. Each balcony is equipped with a railing and simple seating, providing a comfortable space to enjoy the outdoors. A surrounding green area offers a touch of nature.

Home in Norfolk

4.97 out of 5 average rating, 111 reviews

One block from the Beach

Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

Top guest favorite

An aerial view showcases the cottage nestled among trees, surrounded by lush greenery. The serene waterfront is visible, featuring a wooden dock extending into the water. Nearby, a flag fluttering gently adds a touch of charm to the setting.

Home in Portsmouth

4.96 out of 5 average rating, 109 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

“The Captains Cottage” offers a quiet private RIVERFRONT setting. Bring kayaks, paddle board, fish or just sit and bird watch! Enjoy the sunset at this 1500 sq. ft. quaint and cozy 2 story cottage. Hampton Roads has so much to offer, and the Portsmouth area is no exception! There’s a ‘historic downtown’ and a vibrant waterfront only 4 miles from the captains cottage! Need a break from the river? Virginia Beach OCEANFRONT is 30 minutes away! 6 guest limit. Guests of the 2 legged variety.

Guest favorite

A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.

Condo in Virginia Beach

4.9 out of 5 average rating, 210 reviews

Oceanfront Gem VaB Studio Exceptional Views

Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Guest favorite

A well-kept lawn adjoins the beach, featuring several white lounge chairs and a round table with an umbrella for shade. The Atlantic Ocean is visible in the background, along with beach umbrellas dotting the sandy shoreline.

Apartment in Virginia Beach

4.91 out of 5 average rating, 221 reviews

VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool

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

Top guest favorite

A clear view of the expansive backyard showcases a saltwater pool surrounded by a white fence. Beyond the pool, an open sandy area leads to the green grass, and the serene sea stretches across the horizon under a clear sky.

Cottage in Norfolk

4.97 out of 5 average rating, 240 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

A comfortable blue cushioned chair is situated on a wooden deck, offering a serene view of the calm waters of Sarah's Creek. Lush green grass and trees frame the landscape, creating a tranquil outdoor space perfect for relaxation.

Cottage in Gloucester Point

4.99 out of 5 average rating, 134 reviews

Sarah's Creek Starlight

Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

Top guest favorite

Two beach chairs, one red and one blue, are positioned on a sandy beach facing the calm water. Two individuals are seated, enjoying the serene view, with the beach and gentle waves in the background.

Guest suite in Norfolk

4.93 out of 5 average rating, 567 reviews

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

Superhost

The image captures a charming home situated by the water, featuring a welcoming front porch and landscaped lawn. The backyard includes a boat shed and a pathway leading to the river. Nearby greenery and a distant view of neighboring houses are visible across the water.

Home in Hampton

4.83 out of 5 average rating, 125 reviews

Hampton River Retreat Deluxe

The Hampton River Retreat Deluxe is a newly renovated 3 Bedroom/2 bath home on the Hampton River - conveniently located by land or water to all major points in the Hampton Roads area. The quiet neighborhood is close to many features including Downtown Hampton, Langley AFB, Fort Monroe, Buckroe Beach, and a short drive across the HRBT to Norfolk. No parties or events, or gatherings of any kind are allowed in the home.

Top guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 337 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.