Vacation 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!

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

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

Dog-Friendly Cozy Cottage | Private Fenced Yard

Experience the perfect blend of serenity and centrality at this charming 3-bedroom, 2-bath home in Norfolk. Featuring cozy accommodations and a fully fenced backyard, it’s ideal for couples, solo travelers, or small families - with pre-approved dogs welcome! Enjoy a fully stocked kitchen, Wi-Fi, washer and dryer, and ample parking. Located just 5 minutes from the beach and close to Naval Station Norfolk, Little Creek, ODU, and Waterside District, this home has it all for your Norfolk stay!

Cheerful 3 BR Bungalow 1 Block to the Bay!

Experience the perfect blend of relaxation and coastal charm at this cozy 3BR, 1BA bungalow in Norfolk. Featuring 1 King bed, 1 Queen bed, and 1 bunk bed, it’s ideal for families, couples, or small groups. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, pet-friendly stays, and a spacious back deck. Located near the bay, a local brewery, and a BBQ restaurant, you’ll have easy access to calm bay beaches and local dining. Whether for a weekend or an extended stay, this home has it all!

Vintage Cottage on Private Creek–Near Beach & Base

1 mile to Base & Beach. Serene waterfront light-filled vintage cottage in the woods. Nestled in a quiet suburb on a creek, among nature & wildlife. The spacious home is a relaxing respite from the hustle and bustle–a getaway not far away from all Coastal VA has to offer. 20-30 Minutes to Downtown Events, Oceanfront Boardwalk. Perfect for families, romantic retreats or a friends weekend. Sleeps 4, 2 bdrms, 1 sleeping porch, sofa 1,500 sqft, No water activities.

Cobblestone street apartment with rooftop views!

Historic, Downtown area of Norfolk. Walking distance to shops, restaurants, museums, landmarks, parks, memorials, EVMS, & CHKD. This special residence is on the National Register of Historic Homes, includes a clawfoot tub & rooftop patio (no hold harm). This High Victorian Italian home was built in 1870, with a Mansard roof & features an ornamental cast iron veranda. John Cary Weston built this as a summer residence following the Civil War.

The Chesapeake St Retreat - Pet and Kid Friendly!

The kid and pet friendly retreat your family will love! This beautiful 2,200 sqft, four bedroom home is PERFECT for your beach get away and is less than a 5-minute walk from the beach. This home features a stylish design, a dining room table that can seat up to 10, a fenced in back yard for your furry friends. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!!

Beachfront stay with kayaks & paddleboards

Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.

Beachfront Getaway, Pet Friendly, Mermaid Suite

Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

*Escape to the Tangerine Dream*

**ESCAPE TO THE TANGERINE DREAM** in this stunning beachfront oasis, located just steps away from the sandy shores of Captain's Quarters Park, this 3 bedroom/2 bath home offers the perfect blend of luxury and relaxation. Step inside to the open concept living area which boasts breathtaking views from two balconies, perfect for enjoying your morning coffee or watching the sunset over the ocean.

Bayfront backyard with a dock, 3BR, Dogs Welcome!

Welcome to our cool and cozy 3 bedroom, 2 bath home in Norfolk! Featuring a king bed and 2 queens, it’s ideal for families traveling together. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, and laundry! Located in the Willoughby neighborhood of Norfolk, you’ll have easy access to the ocean and all Norfolk has to offer. Whether for a weekend or an extended stay, this home has it all!