Vacation rentals with a kayak in Portsmouth

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Top-rated kayak rentals in Portsmouth

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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, 97 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.

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 Sandbridge
4.82 out of 5 average rating, 136 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 blue, three-story house is viewed from the side, showcasing multiple windows with white trim. A well-maintained path lined with stones leads to the entrance. Two individuals walk towards the house, and a cart is positioned neatly beside plants in the foreground.
Home in Willoughby
5 out of 5 average rating, 12 reviews

Beachfront Getaway, pet friendly

Welcome to your Chesapeake Bay escape—this beachfront duplex offers 6-bedrooms, 4-bath retreat with over 4,100 sq. ft. of beautifully designed space, 2 fully stocked kitchens, 8 plush beds, & beach views. This stylish getaway offers a semi-private beach, open concept living, a breezy outdoor patio with grill, thoughtful touches of home and lots of beach gear. It’s dog-friendly with approval, and pet fee. This is where comfort, class, & coastal charm come together for unforgettable memories.

Guest favorite
A rustic stone fireplace serves as a central feature in the living area, its warm glow inviting relaxation. The high ceiling and exposed beam accents create a spacious atmosphere, complemented by hardwood flooring and comfortable seating arrangements nearby.
Guesthouse in Virginia Beach
4.94 out of 5 average rating, 48 reviews

The Sportman's Lodge

The Sportsman’s Lodge is a rustic and relaxing modern getaway with all the conveniences you are accustomed to but surrounded by the gorgeous Back Bay Wildlife Refuge. Enjoy the relaxing countryside at this waterfront property, while still being only a short drive away from Sand Bridge Beach. If you are looking to get away from the standard Virginia Beach Boardwalk tourist experience and get back to nature, this is the place for you. Free kayaking to Back Bay, access to fishing and crabbing.

Guest favorite
A bright dining area features a wooden table and two chairs, set against three large arched windows. Soft drapes frame the windows, showcasing views of the lush garden outside. A small vase with fresh flowers is placed at the center of the table.
Guesthouse in Cape Charles
5 out of 5 average rating, 36 reviews

Eden Guest Suite on Lake Allure

Relax and recharge in nature at this unique and peaceful getaway. Private access to one of Virginia’s best freshwater fishing lakes, with kayaks and SUP included. Just 15 minutes south of Cape Charles and 5 minutes from Kiptopeake, it’s a perfect base for exploring the Shore. Surrounded by nature and just 3 minutes’ drive to Pickett’s Harbor Farm and beach access. The guest suite is separated from the main house, with a private entrance and beautiful garden views for a truly tranquil stay.

Top guest favorite
An aerial view captures a peaceful waterfront neighborhood, showcasing several homes bordered by lush greenery. The Salt Ponds inlet features boats moored at nearby docks, with a clear blue sky enhancing the serene atmosphere.
Home in Buckroe Beach
5 out of 5 average rating, 76 reviews

The Canary Island … Keep Calm and Fish On

Relax with your family at this peaceful home on the waterfront. Enjoy expansive views of the Salt Ponds inlet with deep water boating access, and miles of kayaking waters. Immerse yourself in the “low country” lifestyle and spend your days fishing, crabbing, boating or sunning at the beaches. The kitchen is stunning, coffee on the deck is a must, the bedrooms are comfortable and the master bath is a retreat to enjoy the amazing inlet surroundings. Pool table, video game table … and more

Guest favorite
A serene view from a wooden dock extends over calm water at dusk. Two Adirondack chairs are positioned to face the horizon, where soft orange light meets a gradient of deep blue sky, reflecting on the water's surface.
Cottage in Sandbridge
4.97 out of 5 average rating, 32 reviews

Bayfront Cottage with Private Dock - Pet Friendly

Sea La Vie Sandbridge is a boutique beach cottage tucked between the ocean and Back Bay. Designed for couples and small groups, it includes bikes, kayaks, beach gear, and cozy outdoor seating. Walk to the beach or explore wildlife trails. Inside, enjoy a fully equipped kitchen, plush beds, and smart features. Thoughtfully curated for rest and connection—no chores, just effortless, memorable stays. smooth, memorable experience. ***Pool is open from Memorial day until End of September ***

Top guest favorite
Home in Virginia Beach
4.91 out of 5 average rating, 455 reviews

3 bedroom 3 bathroom beach house pets welcome

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
An inviting entrance shows a white picket fence adorned with a heart-shaped wreath. Climbing white flowers create an archway over the gate, leading into a well-maintained grassy area. A covered porch is visible in the background, enhancing the outdoor charm.
Cottage in Chic's Beach
4.8 out of 5 average rating, 149 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

This 2 bedroom 1 bathroom quaint cottage is the perfect small family getaway. Located 2 residential blocks to the beach. The beach is great for families with children. This unit is connected to a 1 bedroom rental. Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $100 pet fee with pre approval. ***Summer 2026 check in on Friday only ****

Top guest favorite
A bright sunroom features large windows that frame views of the Chesapeake Bay and surrounding natural landscape. Light-colored furnishings complemented by a wooden coffee table and a small plant enhance the airy feel. The serene atmosphere is accentuated by sunlight streaming through the glass.
Cottage in Bayview
4.99 out of 5 average rating, 152 reviews

Private Beach Access at The OV Beach House

Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided.

Top guest favorite
A beachfront home with a two-story structure is positioned on stilts, overlooking the waves of the Chesapeake Bay. Large windows reflect the vibrant blue of the sky and the inviting design of the house. Nearby houses and green grass complement the coastal setting.
Home in Buckroe Beach
4.99 out of 5 average rating, 109 reviews

Beachfront 2 Dwellings EV charger

Blue Marlin is a private beachfront home on the Chesapeake Bay in Hampton, VA! This home has two dwellings. The 4th bedroom is located in the 2nd dwelling. All four bedrooms are located on the second floor and require climbing stairs. Nestled within 30 miles to the attractions of Busch Gardens, Colonial Williamsburg, and Virginia Beach; our location offers the perfect blend of relaxation and adventure.

Guest favorite
The exterior of a spacious coastal retreat is showcased, featuring a multi-level design with a large deck and white railing. A paved driveway leads to a garage, with ample outdoor space surrounding the property, inviting relaxation and outdoor activities.
Home in Sandbridge
5 out of 5 average rating, 18 reviews

Captain's Corner

Welcome to Captain’s Corner, your luxury escape in beautiful Sandbridge Beach! ✨ Just a minute’s stroll from the ocean, this newly renovated 5-bedroom, 3-bath coastal retreat blends comfort and style for the perfect beach getaway. Relax in bright, inviting spaces, unwind on the deck with ocean breezes, or share sunset dinners with loved ones — every moment here feels effortless and indulgent. 🌊💫

Popular amenities for Portsmouth kayak rentals

Quick stats about vacation rentals with a kayak in Portsmouth

  • Nightly prices starting at

    Portsmouth vacation rentals start at G$14,654 GYD per night before taxes and fees

  • Verified guest reviews

    Over 250 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Portsmouth rentals

  • 4.8 Average rating

    Portsmouth stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Portsmouth's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square

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