Vacation rentals with a kayak in Portsmouth

4.96 out of 5 average rating, 82 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!

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!

4.84 out of 5 average rating, 129 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

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.

4.95 out of 5 average rating, 126 reviews

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

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!

4.99 out of 5 average rating, 185 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

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.

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, 384 reviews

Private Guesthouse on Secluded Waterfront Farm

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.

4.95 out of 5 average rating, 145 reviews

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

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!

4.91 out of 5 average rating, 139 reviews

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

“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.

4.91 out of 5 average rating, 398 reviews

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

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

4.99 out of 5 average rating, 134 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

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. Can accommodate up to 8 people.

4.73 out of 5 average rating, 55 reviews

A wooden dock extends over calm water, surrounded by lush greenery. The reflection of trees can be seen in the water, and a clear blue sky overhead completes the serene lakeside setting.

Home in Portsmouth

3D Theater ~ Firepit ~ Fishing

Enjoy a movie night with our 120" movie screen and high end 3D projector, as well as a selection of 3D movies and rechargable 3D glasses. Relax in the backyard with outdoor dining, a firepit - and best of all, excellent fishing and kayaking from our own private dock! We hope you enjoy the king size bed in the master, and two, comfy double beds in the secondary bedroom. Our amenities are made for a maximum of 6 guests. Guests not on your reservation is a $25 per person fee.

4.79 out of 5 average rating, 145 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

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . 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. Starting June 25th 7 night min check in on Friday only !

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, 263 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.

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Popular amenities for Portsmouth kayak rentals

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House rentals with a kayak

5 out of 5 average rating, 64 reviews

Home in Buckroe Beach

The Canary Island … Keep Calm and Fish On

MichaelRating, 5 stars1 week ago

The property is spectacular. Everything about the accommodations was excellent. Not one complaint. Just praise. The host was very friendly and helpful. So were the neighbors!

5 out of 5 average rating, 18 reviews

The exterior view of a two-story house is showcased, featuring wood siding and a staircase leading to the upper deck. A United States flag waves proudly from a flagpole. Lush greenery surrounds the property, creating a natural setting.

Home in Corolla

Lazy Palm Carova 4x4 Beach

NathanRating, 5 stars3 weeks ago

Great stay! Very quiet location. Walkable to the beach. Host was very responsive and helpful. We can't wait to come back

4.93 out of 5 average rating, 81 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

MikeRating, 5 stars3 weeks ago

We absolutely loved the house and all of the decor! There was no need to leave the house if we didn't want to due to the movies, records, stereo system, arcade machine and hot tub! But, my personal favorite was the kitchen! We will definitely be going back and staying at Adam's!! Side Note: The Legos are AMAZING!

5 out of 5 average rating, 4 reviews

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 Norfolk

Beachfront Getaway, pet friendly

JasonRating, 5 stars7 months ago

Our family enjoyed our weekend at Big Blue. It was special because it was my wife's birthday and there was plenty of family with us. We really liked how the 2nd and 3rd floor are duplicates of each other. It's like 2 different apartments , but we had access to both. The kids on the 2nd floor and the adults on the 3rd. Very clean open spaces. The host were responsive and proactive. We hope to make the Willoughby Spit area a regular vacation spot, very lovely.

4.91 out of 5 average rating, 23 reviews

An aerial view captures the single-story ranch home positioned across from the beach. Sandy shores extend alongside the calm water, while charming residential streets and greenery surround the property, highlighting its prime coastal location.

Home in Cape Charles

FREE Luxury Golf Cart - across from CC Beach

GailRating, 5 stars2 weeks ago

We enjoyed everything about this place! The location was so perfect being steps from the beach & the house so charming! Loved the comfy beds, beautiful decor & the movie projector & screen were a big hit after the day at the beach! Khyber was very responsive to our questions. We would love to stay here again! Thank you, Khyber!

4.9 out of 5 average rating, 10 reviews

A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.

Home in Cape Charles

Hot Tub - Massage Chair - Golf Cart - Beach Gear

ThomasRating, 5 stars2 weeks ago

Nate was very responsive from booking , all the way through our stay. He was very flexible due to our circumstances and juggling vacation with 2 young children and 2 labradors. I would recommend this home to anyone with a family or pets as it offers the interior space that cape Charles historic homes lack while maintaining the same proximity to the town’s attractions.

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.

4.95 out of 5 average rating, 57 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

AmyRating, 5 stars1 week ago

We had a two night stay at this beautiful house. Everything was nice and clean. We loved sitting on the deck, overlooking the river. It was a perfect place to drink our morning coffee!

4.78 out of 5 average rating, 37 reviews

Two wooden Adirondack chairs are positioned on a sandy area beside the calm water. Lush green plants surround the chairs, while a bridge and boats can be seen in the distance reflecting on the water's surface.

Home in Norfolk

Wil-O-Bay Getaway

TamaraRating, 5 stars12 months ago

Absolutely loved this house! Perfect place whine working. Loved sting on the deck out back. Bonnie was wonderful person to communicate with. Would stay again! Thank you

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Cottage rentals with a kayak

Cottage in Norfolk

4.79 out of 5 average rating, 146 reviews

Beach Cottage - On Beach with Wrap Around Porch

BomaniRating, 5 stars1 week ago

good location and a nice place for a getaway from the city

Cottage in Norfolk

4.79 out of 5 average rating, 121 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

ShannonRating, 5 stars4 days ago

This was our second year staying in one of John's places in Oceanview Norfolk. Last year was great but we enjoyed this year even more. This place had more room for our family of 5! It was beautiful inside and out. Very quite and too yourself. But John is usually right there if ya need him or have any questions. We will definitely be back next year. And I'd recommend this place to Any and Everyone looking for a wonderful place too stay! Thanks for sharing your property with us as Always!

5 out of 5 average rating, 23 reviews

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

Epic Sunsets | Waterfront Cottage | Pet Friendly

CateRating, 5 stars1 week ago

This place was the most charming airbnb I have ever stayed in. Badria and Jay made every detail of our stay perfect with all of their extra touches, including saltwater taffy and a box of croissants, slippers and a lavender mask, and a fully stocked coffee station with syrups. We instantly felt at home and in vacation mode at their place and literally laid out on the dock the entire time. A perfect spot for kayaking, laying out in the sun, and I even brought out my mat and did some yoga on the dock. The views were unreal. The couch was so comfortable I accidentally fell asleep there the whole night and woke up to the gorgeous window views. Amazing hosts and location!