Waterfront holiday rentals in Portsmouth

Guest suite in Virginia Beach

4.9 out of 5 average rating, 689 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Farm stay in Cape Charles

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

5 out of 5 average rating, 408 reviews

Guesthouse at Vessel Farm & Winery, Waterfront

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

A serene view of the pool area at sunset showcases warm hues filling the sky. White lounge chairs are arranged around the pool, which is enclosed by a safety fence. In the background, the beach and ocean can be seen, enhancing the tranquil atmosphere.

4.77 out of 5 average rating, 169 reviews

Oceanfront Building Boardwalk Pool Beach 3 Beds

Welcome to the Cozy Crab – updated, comfort-focused & steps from the sand! Located in a quiet corner of a beachfront building on the Virginia Beach boardwalk with a seasonal pool (open mid-May–mid-Oct). Sleeps 4 with 3 real beds: one queen and two singles, all with real mattresses. Features a large, updated bathroom with full vanity and a kitchen. Just a few steps up—no elevator needed. No chore checkout, pro cleaning, fresh linens/towels, WiFi. 2nd-floor grills. Eat! restaurant is downstairs!

5 out of 5 average rating, 289 reviews

A serene dock overlooking the water is framed by trees, where two chairs and a small table are positioned to enjoy the sunset. The warm hues of orange and yellow reflect on the calm surface of the river, adding to the tranquil ambiance.

Cottage in Norfolk

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

Apartment in Williamsburg

A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.

4.94 out of 5 average rating, 140 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.

4.87 out of 5 average rating, 121 reviews

The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.

Home in West Park View

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

4.98 out of 5 average rating, 126 reviews

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 Willoughby

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

4.96 out of 5 average rating, 110 reviews

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

Home in Norfolk

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

4.96 out of 5 average rating, 205 reviews

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Two blue Adirondack chairs are positioned on a grassy area overlooking the beach. A small round table sits between them, providing a place for drinks or snacks. The ocean stretches out in the background, with gentle waves and a pastel sky at sunset.

4.89 out of 5 average rating, 205 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, 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.

4.97 out of 5 average rating, 270 reviews

Cottage in Bayview

Villa Positano

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.

Cottage in Gloucester Point

A serene view of a wooden dock extending into the calm waters of Sarah's Creek, surrounded by trees. Two kayaks, one green and one blue, are positioned on the grassy shore, with a charming cottage visible in the background.

4.94 out of 5 average rating, 288 reviews

The Cottage on Sarah's Creek

Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

Popular amenities for waterfront rentals in Portsmouth

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.96 out of 5 average rating, 27 reviews

A light-filled living space features a comfortable leather sofa and a modern dining table. A TV is mounted on the wall, and a large window allows natural light to illuminate the room. A small indoor plant adds a touch of greenery, enhancing the airy ambiance.

Flat in Chesapeake

Serene Tree House Retreat | Spacious 1br/1bth Home

The Beach Quarters Resort is displayed from an elevated perspective, showcasing its contemporary architecture. The rooftop pool is visible atop the building, with the expansive Atlantic Ocean and sandy beach in the background, illustrating the direct beachfront location.

5 out of 5 average rating, 3 reviews

Direct Beachfront on Boardwalk facing Ocean

4.99 out of 5 average rating, 146 reviews

A garden area is showcased, featuring vibrant pink flowers in the foreground. Lush green grass and hedges frame the view, which extends to a peaceful waterfront scene with trees lining the shoreline. Natural light enhances the serene outdoor atmosphere.

Flat in Yorktown

Yorktown on the Waterfront

A wooden deck is showcased, surrounded by lush greenery. The railing is made of wood with black metal accents. The space offers an inviting outdoor area, nestled in a tranquil environment with a view of trees and a fenced yard.

4.91 out of 5 average rating, 569 reviews

Private apartment only 3 blocks from the Beach

A balcony view captures bright red Adirondack chairs placed on a concrete surface, facing the beach and ocean. The calming horizon displays gentle waves, while a pathway and greenery are visible in the foreground. People can be seen enjoying the beach in the distance.

5 out of 5 average rating, 17 reviews

Oceanfront 2 bedroom condo

4.97 out of 5 average rating, 32 reviews

A private porch area is shown with two cushioned chairs and a small table between them. A potted plant adds a touch of greenery. Sliding glass doors lead into the guest suite, while wooden decking provides a natural feel.

Flat in Sandbridge

Sandbridge Beach Bay Getaway

4.9 out of 5 average rating, 20 reviews

A two-story beach house is shown, featuring a wide front porch with outdoor seating and umbrellas. The driveway provides ample space for parking, and flags adorn the house, adding a coastal touch. Surrounding landscaping includes greenery, enhancing the inviting exterior.

Flat in Sandbridge

Works 4 Me: New listing

5 out of 5 average rating, 44 reviews

A wide sandy beach stretches alongside gentle ocean waves under a clear blue sky. Colorful resort buildings line the beach, creating a welcoming coastal atmosphere. Footprints in the sand suggest leisurely strolls along the shore, inviting relaxation in this serene setting.

Flat in Sandbridge

Bayside condo on the beach in Sandbridge

Waterfront house rentals

4.98 out of 5 average rating, 42 reviews

A bright living space features large windows offering panoramic views of Chesapeake Bay. A comfortable leather sofa and colorful area rug are positioned around a wooden coffee table. A decorative mirror and fireplace add interest to the room, while a stylish desk is situated nearby.

Home in East Ocean View

Private Beachfront Modern Villa: Outdoor Shower!

4.99 out of 5 average rating, 203 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

4.94 out of 5 average rating, 48 reviews

A fire pit surrounded by five colorful Adirondack chairs is set on a gravel circle by the water's edge. The calm waters of Hampton Roads Bay stretch out in the background, providing scenic waterfront views under a clear blue sky.

Home in Portsmouth

Waterfront/Arcade/Fishing Fun

Home in Gloucester County

A wooden dock extends into the tranquil waters, bordered by smooth stones along the shore. Bright blue skies with scattered clouds enhance the natural beauty of the scene, inviting leisurely activities by the water.

4.96 out of 5 average rating, 78 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

4.96 out of 5 average rating, 93 reviews

A grand deck is viewed, featuring two white rocking chairs overlooking a vibrant sunset over the water. The sky is filled with shades of pink and orange, reflecting on the calm ocean surface. A dark wicker seating area is visible to the right.

Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

4.9 out of 5 average rating, 29 reviews

A serene view of a private beach is presented, bordered by a gently sloping green lawn. The tranquil water reflects the sky, while scattered stones and patches of marsh grass create a natural shoreline. A tree stands near the water's edge, adding to the peaceful ambiance.

Home in Suffolk

Respass Beach Cove Cottage

5 out of 5 average rating, 13 reviews

A welcoming entrance features a light blue front door framed by two windows. A small porch, supported by wooden beams, is equipped with a railing. Potted plants line the side of the porch, while brick steps lead up to the entrance.

Home in Portsmouth

Escape to the water!

4.82 out of 5 average rating, 136 reviews

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Sandbridge

Stunning Views of Back Bay & Seconds to the Beach

Waterfront apartment rentals

4.81 out of 5 average rating, 31 reviews

A serene seascape captures the tranquil waterfront at sunset, with soft hues of orange, blue, and pink blending in the sky. A calm shoreline reflects the colors, while silhouettes of birds are seen at a distance, enhancing the peaceful atmosphere of the beach.

Apartment in Bayview

Bay Breeze At Ocean View Beach Home

Apartment in Virginia Beach

A modern living room features a gray sofa adorned with decorative pillows, paired with a light blue coffee table. Two lamps provide ambient lighting. Artwork of coastal scenes decorates the walls, while a patterned area rug enhances the room's coastal theme.

4.98 out of 5 average rating, 129 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

Apartment in Cape Charles

A modern chef's kitchen is presented, featuring a large marble island with seating for three. Sleek cabinetry and stainless steel appliances complement the space. Natural light fills the room, highlighting the wood flooring and elegant design elements, creating a welcoming atmosphere for cooking and entertaining.

5 out of 5 average rating, 25 reviews

The Port - Large condo on Mason Avenue!

4.99 out of 5 average rating, 96 reviews

A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.

Apartment in Willoughby

Beachfront Getaway, Pet Friendly, Mermaid Suite

Apartment in Virginia Beach

A sunset view over the ocean is captured from a balcony, where warm colors blend in the sky. Gentle waves lap at the shore, and silhouettes of distant boats are visible on the horizon. The sandy beach offers a serene atmosphere.

4.87 out of 5 average rating, 154 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Apartment in Virginia Beach

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.

4.98 out of 5 average rating, 104 reviews

Paradise at the Beach

Apartment in Williamsburg

The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.

4.96 out of 5 average rating, 112 reviews

2 Bedroom Stylish Kingsmill condo