Family-friendly vacation rentals in Willoughby Bay

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.

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

One block from the Beach

Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Bungalow at the Bay

This wonderfully decorated home is the perfect spot for a beach getaway with the whole family. Inside you will find a spacious living room, kitchen, bathroom, and two guest rooms with one queen, and a full. Outside there is a backyard porch, perfect for socializing, and a sizable backyard protected by a fence that stretches the property! Free parking is available inside and outside the property. Beach access and free parking is located on 11th view street about a two-minute walk away!

Beautiful renovated 2Bed home!

Your next unforgettable beach getaway awaits with a stay at this charming and completely renovated 2-bedroom, 1-bathroom vacation rental centrally located in Norfolk. Spend sunny summer days at Ocean View Beach, or explore the sights and sounds of nearby First Landing State Park, followed by a quick bite to eat at a local seafood restaurant. At dusk, retreat back to 'Castaway Cottage' for a family BBQ on the propane grill and s'mores shared around the fire pit………………………………

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

Coastal Modern Cabin

Your coastal and modern beach getaway, with everything you need for a great stay! Discover: Across the street from the beach Huge back porch Two egg chairs Air hockey Electric fireplace 75" TV with subscriptions Retro arcade games Board games Bag toss Secluded beach access, no large crowds! Check out the picture descriptions! With 100+ views a day, a guest is on the way! So, book now and enjoy your stay at the Coastal Modern Cabin!

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.

Cozy beach cottage! One block to the beach!

Beach cottage! Dogs sleep for free! One block to the beach. 3 bedroom. 1 bath. 1 king, 1 queen and 2 twin beds. Large deck with outdoor seating and grill! One block from Karla’s Beach House (brunch and lunch). One block from Jessy’s Taqueria. About a mile from Cova Brewing Co. (Brewery and Coffee) and East Beach Farmer’s Market (Saturdays from 9-12). Up to 2 dogs allowed.