Holiday rentals with beach access in Willoughby Bay

Peaceful beach @Courtyard Cottage Pets Allowed

Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.

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!

Dog-Friendly Norfolk Cottage Near Ocean View Beach

🏡 Cozy 3BR cottage sleeping up to 6 guests 🐶 Dog-friendly with pre-approval and fully fenced backyard 🌊 Only minutes from Ocean View beaches 🚗 Ample driveway parking for multiple vehicles 🍽️ Fully stocked kitchen for easy meals at home 📺 Smart TV & high-speed Wi-Fi included 🧺 In-home washer and dryer for added convenience 🌳 Quiet residential neighborhood near local attractions ⚓ Close to Naval Station Norfolk and Little Creek Base 🎨 Easy access to downtown Norfolk, Ghent, and Waterside

Pet Friendly Beach King Bed

Welcome to Your Vibrant Beach Hideaway! Escape to your own slice of paradise in this vibrant 900 sq. ft. 1950s beach bungalow, just 1 mile from Ocean View Beach. Enjoy a peaceful fenced backyard, fire pit, and grill—perfect after a day in the sun. Skip the crowds of VA Beach Oceanfront and unwind in style. With bold design, modern comforts, and beachy charm, this cozy retreat offers the perfect mix of privacy and convenience. Norfolk is a military town you may experience the sound of aircraft.

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

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

Ocean Getaway

Just one block from the beach, this beautifully remodeled apartment is the perfect coastal retreat! Enjoy a stylish, comfortable space with everything you need for a relaxing getaway. Located near top-rated breweries, restaurants, and local favorites — you’ll be right in the heart of all the action. Please note: • This is an apartment unit — no parties allowed • Ring camera at front door for guest and property security • Maximum 1 parking space for Airbnb guests

Stylish Beach House, Hot Tub, Pet Friendly

Welcome to your coastal oasis of relaxation & fun. Enjoy beach fun, hot tub & games in a modern open concept living space. This stylish, pet friendly home away from home is perfect for families. It's 1.5 blocks from the beach. This charming SFH offers 2 bedrooms, loft, chef's kitchen, game room, spacious backyard with deck, hot tub, fire pit, BBQ grill, & volleyball/badminton court. It's centrally located near VA Beach, Williamsburg, & Downtown Norfolk.

902C Coastal Retreat Steps to Beach Sauna Specials

Welcome to 902C Coastal King Retreat, a charming ground-floor unit in a historic 1920 coastal duplex located directly on the Chesapeake Bay. This beachfront 1-bedroom cottage sits just 20 feet from the sand, with private beach access via wooden walkways surrounded by lush landscaping and coastal breezes. Also included is a shared Sauna and laundry room. Off-season specials includes free Kayaks/Paddle-Boards/Beach Chair & Beach Umbrellas starting September 8

Positano Villa

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.

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ

Escape to our charming Airbnb, just steps from the beach! Perfect for groups up to 8, our home offers ultra-fast 1Gbps fiber internet, a dedicated workspace, and delightful amenities including a SCA-approved coffee maker, a grinder, and fun games like a giant Connect 4 and Foosball. Enjoy the outdoors with our two patios and a BBQ grill. With numerous local restaurants nearby, it’s the ideal getaway for both relaxation and adventure.

Life on a Sandbar right on Chesapeake Bay

Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!