Vacation rentals with a kayak in Hampton Roads

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Top-rated kayak rentals in Hampton Roads

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Superhost

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 Virginia Beach

4.85 out of 5 average rating, 134 reviews

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

Guest favorite

The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.

Condo in Williamsburg

4.95 out of 5 average rating, 132 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

This beautiful, 2B2Ba condo is 1400 sq.ft. in the exclusive Kingsmill neighborhood. This 1st floor unit has two master suites w/ king beds. One features a luxurious bathroom w/ a walk-in shower & dual shower heads, the other has a shower/tub combo as well as a private patio, stepping out onto the 9th Fairway. The open-concept living space has dining for 6, a queen sleeper sofa, a fully stocked kitchen, and an additional private patio. Golf course views from anywhere in the main living space!

Top guest favorite

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

4.99 out of 5 average rating, 198 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

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.

Farm stay in Cape Charles

5 out of 5 average rating, 400 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.

Guest favorite

A classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

Home in Cape Charles

4.94 out of 5 average rating, 151 reviews

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

Superhost

The kitchen area features dark cabinetry and a modern design, with a large sink and stove. A microwave is mounted above the stove, and a mounted TV can be seen nearby. Marble-like countertops enhance the space, which is well-lit by natural light.

Camper/RV in Portsmouth

4.87 out of 5 average rating, 157 reviews

“Genevieve” the glam RV perfect for R & R!

Genevieve is a 30 foot stunning Design RV that is located in Parkview Portsmouth, Virginia. It provides a glamping experience and a comfortable stay while your on vacation. This beautiful modern RV provides an experience of unwinding, relaxation and style. Escape the stress of a busy schedule and experience this gem. We are situated on a private residence walking distance from the Elizabeth River. Olde Towne Portsmouth, scenic views & minutes away from restaurants, grocery shopping and more.

Top guest favorite

The kitchen features modern appliances, including a stainless steel refrigerator and an oven with a cooktop. Rich wooden cabinets provide ample storage, while a large granite countertop offers space for meal preparation. A circular skylight allows natural light to enhance the inviting atmosphere.

Home in Virginia Beach

4.91 out of 5 average rating, 421 reviews

Pet friendly 3 bedroom beach house

Welcome to your perfect vacation getaway! This remodeled 3-bed, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. Bedrooms are equipped with comfy beds. Pet-Friendly: The spacious backyard and deck are perfect for playtime and relaxation. Great location close to shopping and restaurants. You’ll feel right at home in this safe neighborhood. Please note: No parties. Only 9 people are allowed at the house at any time

Guest favorite

A view from a deck showcases an open area leading to the beach, with a decorative arrangement of flowering plants in white planters. An American flag stands proudly in the background, while the calm waters of the bay reflect the clear blue sky.

Cottage in Norfolk

4.91 out of 5 average rating, 190 reviews

Poseidon - Beach Carriage House - 120 Years Old

Your Bayfront Vacation Spot. If you want to spend good family time, a romantic getaway, or live in a cool place while working here, this is your spot. Our neighborhood is located on the shores of the historic Chesapeake Bay. Step onto our beach and you will see that we are the perfect spot for sunrises/sunsets, fishing/crabbing, sunbathing, grilling & hot tubbing. The rental isnt on the beach-side of the property so walk around the building to the beach which is only 30 feet away.

Top guest favorite

A serene waterfront view showcases a gently sloping yard leading to a wooden dock. A well-maintained path lined with decorative rocks is seen, along with lush greenery and trees bordering the water's edge, inviting relaxation in a tranquil outdoor setting.

Home in Lanexa

4.96 out of 5 average rating, 214 reviews

Williamsburg Hide-A-Way Creekside

Cozy home, updated decor, full kitchen, 3 bedrooms (all Queen beds), 2 baths overlooking a gorgeous creek that is too beautiful to describe. Minutes from Colonial Williamsburg, Busch Gardens yet rural, private and quaint. Screened, 3 season porch with heat and A/C, gated deck for kids and pet containment, propane grill, fire table, swing set, boat ramp, kayaks. Enjoy a totally relaxing experience with homelike accommodations. **Pet friendly upon owner approval of breed, age, etc.

Superhost

A wooden dock extends into calm waters, reflecting a soft sunset with pastel hues. A covered boat slip is positioned at the end of the dock, framed by the serene landscape of trees on the horizon.

Home in Charles City

4.84 out of 5 average rating, 109 reviews

Chickahominy Riverside Guest Home By Williamsburg!

Our river-side guest house has everything you will need to enjoy your getaway! Enjoy the river, dock, 2 kayaks, 1 canoe, large game room, portable fire pit, playground, zip-line, basketball goal and large outdoor sitting area with a gas grill. Located 5-20 mins from the finest wedding venues, nearby wineries; less than an hour to Richmond & 25 minutes to Colonial Williamsburg. Only steps to numerous historic plantations & a few miles from the Virginia Capital bike & walking trail.

Top guest favorite

A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

Tiny home in Cape Charles

4.98 out of 5 average rating, 334 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.

Top guest favorite

A vibrant sunset paints the sky in shades of orange and pink, casting reflections on the water. Silhouettes of a dock and surrounding trees create a serene waterfront scene, highlighting the natural beauty of the location.

Home in North

5 out of 5 average rating, 100 reviews

The Llama House

Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.