Holiday rentals in Willoughby Bay

4.96 out of 5 average rating, 529 reviews

Guest suite in Hampton

Storybook Cottage

Beautiful studio within walking distance to downtown Hampton waterfront, marinas, shopping, dining, microbreweries, arts & museum district. Short drive to beaches, NASA/Langley AFB, Hampton U., and Ft. Monroe. Centrally located off I-64 between Williamsburg and Va. Beach. Quiet and cozy. Has private front and rear entrances and covered private back porch. Perfect for couples & business travelers. Complimentary coffee, tea , water, etc. No 3rd party reservations. Self check in after 3 pm.

4.79 out of 5 average rating, 34 reviews

Apartment in Norfolk

August Suite | Beach | Balcony | Fire Pit

Nestled between two bodies of water, the August Suite is newly renovated and just a 2-minute walk to the beach! Enjoy your morning coffee on the peaceful back porch. This charming retreat features all amenities for an enjoyable stay, including a fully stocked kitchen, comfortable living space, beach chairs, and fire pit. Perfect for relaxing after a day of exploring the area. Experience the best of walkable beachside living while being a quick 5-minute drive to shops, dining, and nearby parks.

4.92 out of 5 average rating, 106 reviews

Boat in Norfolk

Romantic Sailboat Experience by Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. After a wonderful meal at the marina seafood restaurant our guests love to snuggle up together on deck and watch the sunset turn the sky pink & purple with a glass of bubbly. The marina atmosphere is simply magical & you'll love sleeping to the gentle sway of calm waters. Come enjoy a night aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

4.92 out of 5 average rating, 39 reviews

Townhouse in Norfolk

~Summer Fun~ at "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 family get-togethers!

4.97 out of 5 average rating, 116 reviews

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

4.85 out of 5 average rating, 103 reviews

2-Bedroom Beach Bungalow

Two-bedroom condo across the street from the beach. Closest beach access 1 block down, or vacant lot to access beach across the street. Access to house via 1 set of stairs, no elevator. Heat/AC, dishwasher, w/d, and deck. Linens, bath towels, beach chairs, toys, and towels provided. Quiet family beach, bay water is calm- perfect for children. Close to Norfolk military bases and ODU, EVMS, NSU, Virginia Wesleyan, Hampton University. Approx 25 min from downtown Virginia Beach and Williamsburg.

4.84 out of 5 average rating, 115 reviews

Bungalow at the Bay

This wonderfully decorated home is the perfect spot for a beach getaway with the whole family. Inside you will find a spacious living room, kitchen, bathroom, and two guest rooms with one queen, and a full. Outside there is a backyard porch, perfect for socializing, and a sizable backyard protected by a fence that stretches the property! Free parking is available inside and outside the property. Beach access and free parking is located on 11th view street about a two-minute walk away!

5 out of 5 average rating, 4 reviews

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

Welcome to the Blue Octopus! This charming coastal retreat offers comfort and convenience for your seaside escape. Just a short walk to the beach, it's perfect for families, couples, or solo travelers. Location Highlights: 3 minutes to the beach 10 minutes to restaurants & Norfolk Naval Base 15 minutes to outlets 20 minutes to VA Beach Features: Private Pool Hot Tub Outdoor Movie Projector BBQ Grill Home Office Smart TV & Wi-Fi Kid-Friendly Book your stay today!

4.98 out of 5 average rating, 85 reviews

Cottage in Norfolk

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!!!

4.99 out of 5 average rating, 348 reviews

Guest house in Hampton

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.

4.86 out of 5 average rating, 110 reviews

Huge Yard, Great for Families! Walk to Beach!

Experience the perfect mix of relaxation and style at this tastefully designed 4 BR, 2-bath home in Virginia. With 2 queen beds, 3 single beds, and 1 bunk bed, it’s ideal for families or groups! Enjoy a workspace, laundry, backyard, and patio. Near Willoughby Beach and Monkey Bottom Park, you’ll have easy access to beaches and dining. Book today—we can’t wait to welcome you home!

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Popular amenities for Willoughby Bay holiday rentals

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Pool

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Other great holiday rentals in Willoughby Bay

Cottage in Norfolk

4.73 out of 5 average rating, 11 reviews

2 bedroom 1 bath Cozy Beachfront

RhondaRating, 5 stars2 weeks ago

Brian was a wonderful host, and the beach cottage was absolutely beautiful. It reminded me of my grandmother’s home, which made the experience even more special. My family and I were so happy staying there—it truly felt like a home away from home. We hope to return soon.

Guest house in Norfolk

5 out of 5 average rating, 3 reviews

BoatHouse on the Bay - Romantic, Pet Friendly

DennisRating, 5 stars12 months ago

gerda and George are 100% 5 star hosts. they respond right away. they go above and beyond to correct any issues that may arise. the beach side hideaway was the perfect quiet spot with a second 30 walk to the beach. absolutely loved it there and will definitely be reserving for future get aways. Tha k you gerda and george

4.79 out of 5 average rating, 14 reviews

Short walk to beach! Dogs welcome!

TeriRating, 5 stars1 month ago

The location was perfect and was incredibly close to the public beach access. The host was quick to respond to any questions and gave clear and easy instructions. A warning: our van scraped getting in the driveway if anyone was in the middle since it had a large bump to get in, but we just let the passengers out before pulling in and it was fine.

4.87 out of 5 average rating, 245 reviews

Private room in Norfolk

PRIVATE ROOM near EVMS ODU Ghent Base

LashandaRating, 5 stars3 weeks ago

The bed was everything !!!!! so comfy. Beautiful decor. Nice lighting. And the room was cool enough without the fan and not cold. It was really close to a really good breakfast spot call The Bird. I wasn't driving but I could walk there. It located by the water which is really after break I sat by the dock. Her house is peaceful I'm not a light sleeper but when ready for bed I like peace and quiet and I had just that. If I am headed back this way I will book here if available. I loved my stay.

4.91 out of 5 average rating, 111 reviews

Private room in Norfolk

Upstairs Private Room in Ocean View

AngelaRating, 5 stars2 weeks ago

We loved staying here. Her and her husband were very friendly along with their cat LEO!! We had the bathroom all to ourselves down the hall and we’re not ever bothered by them. We would stay there again in a heartbeat if we go out to Norfolk again. Totally great place to stay!!!

4.8 out of 5 average rating, 20 reviews

Hawaii House! 1 block to beach, 6 beds, 2 arcades!

JenniferRating, 5 stars1 week ago

Loved our stay. The beach was the perfect place for our family to watch our sailors ship come in from deployment. Larendal and John were very quick to respond the few times we needed to contact them. Would definitely stay here again.

5 out of 5 average rating, 16 reviews

Guest suite in Norfolk

Welcome to the Sea Suite!

RuthellenRating, 5 stars1 month ago

It was refreshing to stay steps away from the beach and to have a private access to it. Keatha brought the serenity of the Atlantic Ocean into the beachside airbnb by way of a wave sound machine near the comfortable bedding… such a nice touch. Keatha was accommodating and offered us an early checkin and told us about some good local places to eat and enjoy. It is a nice spot for a little refreshing getaway!