Family-friendly holiday rentals in Willoughby Bay

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.

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

Beach Hideaway 2 bdr/2bth- Pet friendly!

Great home for days at the beach and a fire pit at night! Beach access 1 1/2 blocks from the home. Heat/AC, dishwasher, w/d, and deck. Linens, bath towels, beach chairs, and beach towels are provided. Quiet family beach, bay water is calm- perfect for children. Large back yard for kids to run around, deck, and enclosed front porch. Close to Virginia Beach, Norfolk military bases and ODU, EVMS, NSU, Virginia Wesleyan, Hampton Univ. Approx 25 min from downtown Virginia Beach and W-burg.

Castaway 2 bed cottage by the beach

Your next unforgettable beach getaway awaits with a stay at this charming and completely renovated 2-bedroom, 1.5-bathroom vacation rental centrally located in Norfolk. Spend sunny summer days at Ocean View Beach, just 1 block away, 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.

Villa Positano

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

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!

Bungalow at the Bay

Beautifully decorated and perfect for a family beach getaway. Enjoy a spacious living area, full kitchen, 2 comfy bedrooms (queen + full), and a relaxing porch. The large fenced backyard is great for hanging out. Free parking on-site, plus beach access and free parking on 11th View St, just a 2-minute walk away.

Private Guest House in Historic Downtown

This rare-find is a place that's both historic and one-of-a-kind. At just 475 sqft, it is a quaint and cozy stay. This 2 story "summer kitchen" has been renovated (2022) for your comfort. Free Parking across the street at the first library of Norfolk.