Vacation rentals with a kayak in Portsmouth

4.94 out of 5 average rating, 115 reviews

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

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.

LocationValueBeach

4.88 out of 5 average rating, 112 reviews

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

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!

ValueOutdoor spacesCondition

4.89 out of 5 average rating, 225 reviews

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

902 CH Carriage House 20 Steps to Beach & Specials

902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Beachfront Grilling. Specials - Free Kayaks/Paddle-Boards/Beach Chair & Beach Umbrellas starting September 8 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 1-bedroom, 1-bath carriage house now blends timeless charm with modern comfort — offering guests a truly unique and peaceful bayfront getaway.

Outdoor spacesValueLayout

5.0 out of 5 average rating, 81 reviews

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

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

ValueLocationQuiet

4.91 out of 5 average rating, 22 reviews

The spacious living area features large windows allowing abundant natural light, showcasing views of the bay. A game table is central to the room, surrounded by comfortable seating. A piano is positioned against the wall, along with decorative elements that enhance the welcoming environment.

Home in Norfolk

Oceanfront Escape Private Beach

Our waterfront home on Willoughby Bay! Why You’ll Love It: With a small private beach in the backyard for a peaceful escape, and a larger beach just a 5-minute walk away Piano & guitar for music lovers to enjoy Game table for fun-filled nights 4+ private parking spots Spacious 2,800+ sqft open floor plan with bay views Close to Willoughby boat ramp great for boaters Whether you're soaking up the sun, making music, or watching the sunset over the water, our home is a perfect retreat.

LocationOutdoor spacesAmenities

4.76 out of 5 average rating, 96 reviews

Home in Portsmouth

Waterfront Fun: Kayaks, Fishing, Gaming + Theatre

🎬 Movie Nights & Waterfront Fun 🌊 Host your own movie night on a 120" screen with high-end 3D projector, a library of 3D films, and rechargeable glasses for everyone. Step outside to a backyard retreat with outdoor dining, fire pit, and direct access to our private dock for fishing and kayaking. Sleep easy with a king bed in the master and two comfy doubles in the guest room. The home accommodates up to 6 guests. Please note: any visitors not on your reservation are $25 per person.

Outdoor spacesLocationBeach

4.78 out of 5 average rating, 156 reviews

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

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 ****

ValueOutdoor spacesTV

4.83 out of 5 average rating, 149 reviews

Home in Sandbridge

Bayfront Pool Retreat, Walk to Beach

Experience one of Sandbridge’s most unique waterfront retreats, featuring a private pool overlooking Back Bay, plus a private dock and boat ramp right on the property. Just a short walk from the beach, you’ll enjoy the rare combination of bay and ocean access in one location. Newly refreshed on the exterior, this spacious 6-bedroom home is perfect for boating, fishing, kayaking, relaxing poolside, and taking in spectacular sunsets and sunrises.

ValueLocationCondition

4.93 out of 5 average rating, 40 reviews

An aerial view captures a beachfront duplex with light-colored siding, surrounded by grass and sand. Parking spaces are visible in front of the units, along with several vehicles. The nearby beach and water are seen in the background, emphasizing direct beach access.

Home in Norfolk

Oceanfront Cozy Beach Duplex

Wake up to stunning ocean views in this beachfront duplex in East Ocean View, Norfolk! Each 2BR unit offers cozy comfort, a full kitchen, fast Wi-Fi, and direct beach access just steps from your door. Perfect for family vacations, couples, or group getaways. Enjoy sunrise views from the bedroom, sandy strolls, and easy access to local dining. Free parking, smart TV, and self check-in included. Perfect spot for a family vacation.

Outdoor spacesValueCheckout

4.99 out of 5 average rating, 186 reviews

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 Norfolk

Beachfront stay with kayaks & paddleboards

Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.

ValueLocationKitchen

4.93 out of 5 average rating, 120 reviews

The exterior of a modern tiny home is illuminated by a radiant sunset, creating striking sun rays. The home features a spacious deck with steps leading to the ground. Nearby, similar structures are visible against a backdrop of vibrant sky colors.

Tiny home in Sandbridge

Jen n John's Mini Mansion.

Welcome to Surfside at Sandbridge!!! Sandbridge is the northern most portion of the OBX!!! Location location location. There is a queen adjustable bed in the downstairs bedroom, and two twin mattresses in the loft. This unit comes fully stocked for everything you'd need for a beach vacation. Towels..chairs..beach canopy..boogie boards.. Wheeleez beach cart.. kayak…pedal boat… beach cruisers.. etc.

ValueLocationFamily