
Vacation rentals with a kayak in Portsmouth
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Portsmouth
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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.

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.

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.

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.

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.

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

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 ***

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

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 ****

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.

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.

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
House rentals with a kayak

Two Pools + Hot Tub - Come Visit The Golden Hour

Cape Charles Home: Private Pier & Beach-Front Deck

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

Sandbridge Ocean Paradise, Pool, Hot Tub,

Wil-O-Bay Getaway

Offseason special stay 3 nights get 4th night free

Oceanfront Escape Private Beach

Summer House lake/yard/pool/fire pit/volleyball
Cottage rentals with a kayak

Captain’s Cottage at Willoughby Spit Beach

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 B Seaside 2BR Cottage w/ Bay Views & Veranda

902 CH Historic Carriage House 20 Steps to Beach
Other vacation rentals with a kayak

Pet-Friendly Condo Steps to Beach

Three Little Birds-Kayak, fish, bike, enjoy!

Efficiently 2 bedroom 300 B

Simple, country cottage in the woods.

Sandbridge Beach House on the Bay

Back Bay Getaway Beach Retreat

Beautiful Bay Sandbridge Retreat

TOP 1% Award - Spirit Bear Lake Private, Peaceful
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
Destinations to explore
- New York Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Jersey Shore Vacation rentals
- Myrtle Beach Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Cape Fear River Vacation rentals
- Jersey City Vacation rentals
- Waterfront rentals Portsmouth
- Rentals with an EV charger Portsmouth
- Rentals with a washer and dryer Portsmouth
- Rentals with a fire pit Portsmouth
- Fitness-friendly rentals Portsmouth
- Condo rentals Portsmouth
- Family-friendly rentals Portsmouth
- House rentals Portsmouth
- Rentals with lake access Portsmouth
- Rentals with outdoor seating Portsmouth
- Rentals with a fireplace Portsmouth
- Apartment rentals Portsmouth
- Rentals with pools Portsmouth
- Pet-friendly rentals Portsmouth
- Rentals with beach access Portsmouth
- Rentals with breakfast Portsmouth
- Rentals with a patio Portsmouth
- Rentals with a kayak Virginia
- Rentals with a kayak United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Norfolk Botanical Garden
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Red Wing Lake Golf Course




