Vacation rentals with a kayak in Hampton Roads

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Top-rated kayak rentals in Hampton Roads

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

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Top guest favorite

A single-story house is framed by vibrant flowering bushes and trees. A red flag is prominently displayed near the entrance. The front yard is spacious with grassy areas, and a paved driveway leads to a single-car garage.

Home in Newport News

4.94 out of 5 average rating, 112 reviews

1-Bedroom Home Near Christopher Newport University

Sip a bourbon while you listen to a record on the vintage player. Create your CD playlist to pop in the 90s 5 disk changer while you cook on a seasoned cast iron on the new stove. Check out the coffee bar for home roasted beans. Soak in the hot tub, or get a high score on Dig Dug. Centrally located in Newport News near CNU. 25-30 minute drive to Busch Gardens, Water Country, and Colonial Williamsburg. 45 minute drive to the ocean front. Great neighborhood with sidewalks for running and walking.

LocationValueSleep quality

Guest favorite

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 Hampton

4.95 out of 5 average rating, 111 reviews

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

If you enjoy majestic ocean views from almost every room & your own exclusive beach just steps below, Bay Bliss is for you! The panoramic views from this luxury home are unmatched & sure to relax you! Sip coffee from the grand deck or take a soak in the hot tub w/ breathtaking views. Cook/eat in the high-end chef's kitchen or watch a movie on a 75" TV all with stunning views! Wake up in the plush, king-sized bed and enjoy views of the water without having to get up. Your bliss at the bay awaits!

ValueLocationKitchen

Guest favorite

A vibrant sunset casts a warm glow over the water's surface, reflecting hues of orange and red. Silhouettes of trees outline the scene, while grasses along the shore add texture to the landscape. The tranquil water invites moments of reflection.

Cottage in Lanexa

4.94 out of 5 average rating, 122 reviews

"Waterfront! The Lilypad on Mill Creek-Near Wmsbg"

The Lily Pad on Mill Creek provides lovely waterfront views, private dock, wifi, private parking and all the comforts of home! The entire home has been recently renovated, including new HVAC, electric and plumbing and all new appliances! Secluded location to enjoy fishing, kayaking, (kayaks and life vests provided)swimming, canoeing and enjoying the wildlife.Just minutes away from local restaurants and there are two local boat ramps, less than ten minutes away. Have your boat at your fingertips!

LocationOutdoor spacesSleep quality

Superhost

A backyard patio offers seating at a rectangular table with four chairs, shaded by a large umbrella. A cozy seating arrangement is visible nearby, featuring bright cushions. The in-ground pool reflects the sky, while the tranquil river and greenery create a serene backdrop.

Home in Hampton

4.9 out of 5 average rating, 110 reviews

The Great River Escape *Hot Tub!

Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

LocationOutdoor spacesIndoor spaces

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, 220 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.

Outdoor spacesValueKitchen

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, 428 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.

LocationOutdoor spacesSolo travel

Top guest favorite

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

4.87 out of 5 average rating, 136 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, two kayaks, paddle board, canoe, large game room, portable fire pit, playground, 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.

LocationValueAmenities

Top guest favorite

Guesthouse in Gloucester

5 out of 5 average rating, 196 reviews

Summer Escape - Dock, Pool, Firepits, & Kayaks

A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

Outdoor spacesLocationComfort

Superhost

Cottage in Norfolk

4.77 out of 5 average rating, 162 reviews

902 B Historical Beachfront Duplex Sauna & Hot Tub

902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & with rental beach chairs, kayaks and Standup paddle boards on-site. Step back in time at the Historic Carriage House, a beautifully restored 120-year-old gem just 20 feet from the Chesapeake Bay. Once home to horses and rowboats in the early 1900s, this 2-bedroom, 1-bath carriage house now blends timeless charm with modern comfort — offering guests a truly unique and peaceful bayfront getaway.

Outdoor spacesValueGetting around

Top guest favorite

A spacious wooden dock extends over the water, featuring four teal Adirondack chairs positioned for relaxation. Lush greenery surrounds the calm waterway, and a clear blue sky is visible above, creating a serene setting for enjoying nature.

Home in Gloucester

4.9 out of 5 average rating, 113 reviews

Severnly Pointe Cottage Waterfront Retreat

Relax with the whole family at the peaceful "Severnly Pointe" Cottage just off the Mobjack Bay. Surrounded by water on 3 sides and a private dock, enjoy secluded access to everything the water provides. Kayak, fish or just enjoy the rivah breeze on the spacious dock with friends. Launch your boat at the private concrete boat launch on the property. Home is well equipped and enjoys water views from all 4 bedrooms. Only 10 a minute boat ride to the “fishing haven” Mobjack bay.

LocationOutdoor spacesWifi

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, 356 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.

LocationValueHeating

Guest favorite

The exterior of the beach house is captured on a sunny day, featuring a two-story structure with upper and lower decks surrounded by a large green lawn. An American flag gently flutters in the breeze, and parking space is available nearby.

Home in Mathews

4.88 out of 5 average rating, 165 reviews

Piper’s Landing: Relaxing beach house near the Bay

This home is ideal for those who enjoy nature, as it is close to Bethel Beach Park and Nature Preserve and has easy kayak access via a public dock within 2000 feet. The home has two double beds, one king bed, and several couches up stairs . Our perfect getaway includes two kayaks, and a couple adult bicycles, You are only 2 Minutes from Bethel Beach Nature Preserve 15 minutes from Mathews 60 Minutes to Virginia Beach 60 Minutes to Williamsburg/Jamestown

ValueOutdoor spacesBeach