Holiday rentals in Willoughby Spit

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!

Beach House~Hot Tub~3 Min to Sand~HUGE Kitchen

Welcome to the Beach House! This newly renovated home is the perfect stay for a family getaway. Minutes to a quiet beach and a family friendly park! 3 minutes to the beach 10 minutes to amazing restaurants 10 minutes to the Norfolk Naval Base 15 minutes to Norfolk premium outlets 20 minutes to VA beach Features: *Huge Kitchen *Hot Tub ⋆BBQ Grill - propane not provided ⋆Smart TV ⋆Wifi ⋆Sunroom ⋆Kid Friendly ⋆Outdoor space Note: A Carriage House Airbnb is located in the rear of the property.

Family Retreat by the Beach

Step into our beautiful beach retreat just a 3 minute walk from the beach! Inside are 3 large bedrooms- each with their own private bathroom as well as an additional half-bath on the main level. Play pool or ping pong on our convertible dining room table! The kitchen is fully equipped with all you need including a Kuerig coffee maker and complimentary k- cups. Hang out in the backyard which comes with a charcoal grill, yard games and 3 relaxing sitting areas; perfect for a family get-together.

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

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

Pet Friendly Beach King Bed

Welcome to Your Vibrant Beach Hideaway! Escape to your own slice of paradise in this vibrant 900 sq. ft. 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.

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.

Beach cottage w/hot tub

Experience a bright, cozy beach cottage just minutes from the shore and a family‑friendly park. The 440 sq ft studio provides a well‑appointed retreat for couples or a small group. - Sleeps 2‑4 | 1 bedroom | 1 queen bed | 1 bath - Private deck w/ seating, with hot tub - Fully equipped kitchenette: coffee, microwave, mini‑fridge - Smart TV & complimentary Wi‑Fi - Fresh linens & basic beach gear provided - Quiet location minutes from beach & park with calm waters

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

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

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!!!

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.