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!

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

*Beautiful Water Views* King Bed*Fast WIFI

Do you desire Peace, Quiet & Tranquility? This townhome is the PERFECT getaway! It's RIGHT on the water and features the following: *Newer Furnishings! *Blazing Fast Panoramic WIFI & Dedicated Workspace *Bedroom 1: KING size bed overlooking the water. Not a bad way to wake up?!? *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, complete w/a Convection Oven & Coffee Maker & Creamers * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.

Dog Friendly, Large Yard, Spacious & Sleeps 6!

Experience the perfect blend of tranquility and convenience in this charming 3-bed, 2-bath Norfolk home. With a spacious layout and cozy beds, it’s ideal for families and their four-legged friends (pre-approval required; inquire for rules before booking). Features include a fenced yard, a fully stocked kitchen, Wi-Fi, and a quiet cul-de-sac setting. Just a short walk to the beach, you’ll have easy access to the sand and nearby attractions. Book your extended getaway today!

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………………………………

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

3 bedroom private home a block from the beach!

Relax with the whole family at this peaceful home. A block to the beach! 3 bedrooms and 2 bathrooms, with an outdoor shower and finished basement with extra living space. Outdoor patio with gas grill and patio furniture. All amenities included sheets, towels, cooking utensils, etc. Fast Wi-Fi throughout the home. Can sleep up to 8! Pets always welcome. All bedrooms are on main level no stairs required. Weekly and monthly discounted rates upon inquiry.

3BR Mid-Century Modern Home • Near Airport

Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!

*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.

2 Min Walk to Beach • Fenced Yard • Parking

Enjoy a relaxed beach getaway in this beautifully decorated Norfolk home 🌊 Just a short 2-minute walk to beach access, this cozy retreat features a spacious living area, full kitchen, two comfortable bedrooms, and a private fenced backyard. With free parking and a peaceful setting, it’s the perfect spot for families, couples, or a quiet coastal escape.

Spring Hill Guest Cottage - Portsmouth

Two room guest house with full bath and 1/2 bath, kitchenette and sitting room Sits on 9 acres. Adjacent to an occupied 300+ year old house that dates back to the 1700s. Shared access to in-ground pool and adjacent Jacuzzi with owners, but you will have exclusive use during your booking.

Best Value Condo in Downtown Norfolk

This unique place has a style all its own for a romantic getaway or work away from home. The Luxurious apartment is in the heart of Downtown Norfolk!!!! Great restaurants, Bars, Live Entertainment, Concerts, Mall, Waterside, Nauticus and more within 10 mins walking distance.