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Family-friendly vacation rentals in Willoughby Bay

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Willoughby Bay family-friendly rentals

Family-friendly home rentals with a hot tub

Vacation home in Virginia Beach
5 out of 5 average rating, 4 reviews

1 Block to the Beach, Indoor Pool Great 4 Kids

NakimaRating, 5 stars46 months ago
Bijan’s place was amazing! My husband and two small children were very comfortable here. The places offers all the comforts of home and all staff went above and beyond to ensure your stay was nothing short of great. Not only is there an indoor pool to splash and play in with the kiddos, it is directly across the street from the ocean and in close proximity to so many great restaurants. Definitely a must place stay I guarantee you will love it just as much as we did. We will definitely be looking at staying here again in the future!
Superhost
Condo in Virginia Beach
5 out of 5 average rating, 4 reviews

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

AldoRating, 5 stars9 months ago
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.
Superhost
Condo in Williamsburg
4.73 out of 5 average rating, 26 reviews

Wyndham Governors Green Resort- 2 bdrm -2 nt min

RosemaryRating, 5 stars4 months ago
Great place in a great location. We loved having our own space with two bedrooms and a full kitchen only a short drive from Colonial Williamsburg.
Hotel room in Williamsburg
4.6 out of 5 average rating, 15 reviews

Wyndham Kingsgate * 2BR

DanielRating, 5 stars47 months ago
Place was great. Family loved it. Plenty to do. Communication was great and check in and out was a breeze!
Guest favorite
Home in Virginia Beach
4.74 out of 5 average rating, 86 reviews

7+ Bdrm, 5.5 Bath Pool/Hot Tub Sandbridge Beach VA

DaniseRating, 5 stars7 months ago
Owner very responsive and easy to communicate with. Great location
Guest favorite
Condo in Williamsburg
4.78 out of 5 average rating, 9 reviews

Historic Powhatan resort 2 bdrm

JasonRating, 5 stars5 months ago
Colleen was a wonderful host and I would highly recommend this spot!
Condo in Williamsburg
4.92 out of 5 average rating, 24 reviews

King's Creek Plantation: 2-BR, 2.5 Baths, Sleeps 6

HunterRating, 5 stars1 week ago
Good location next to the water park and Target. Quick response for short notice trip. Stronger than. Good quality furniture and new flooring.

Family- and pet-friendly home rentals

Guest favorite
Home in Virginia Beach
4.96 out of 5 average rating, 130 reviews

Water Oaks at Chic's Beach

ClaireRating, 5 stars1 month ago
I could not recommend this place and these hosts enough! The place was warm and welcoming and I absolutely love the location. A very peaceful neighborhood with easy bay access. The hosts were amazing and responsive. The house had some maintenance problems but at no fault of theirs…just typical house problems and they handled everything extremely well and we were not inconvenienced at all! Also our dog loved the place and they were stocked will all the dog necessities which was very helpful!
Guest favorite
Apartment in Williamsburg
4.85 out of 5 average rating, 169 reviews

Westgate Historic Williamsburg One Bedroom

JordanRating, 5 stars3 weeks ago
We had a great stay at Eddie's place! Very close to restaurants, Colonial Williamsburg, and Busch Gardens. The unit we stayed in was spotless and had all of the amenities that we needed during our stay. Highly recommended!
Guest favorite
Home in Williamsburg
4.84 out of 5 average rating, 80 reviews

2 BR Family & Pet Friendly House - Williamsburg

DavidRating, 5 stars8 months ago
Charlene is a wonderful and very responsive host. This was our second time staying there when we visit Williamsburg. The location is great and only a few minutes from everything. The house was comfortable and had everything we needed to enjoy our week. We look forward to staying again in the future.
Guest favorite
Guest suite in Virginia Beach
4.89 out of 5 average rating, 626 reviews

Quiet Neighborhood 7 Miles From the Beaches

CeceliaRating, 5 stars3 days ago
Mona is a sweetheart, and her place was perfect for my dog and me. It was clean and had the cutest backyard. Will definitely book again with her if I’m back in Virginia Beach
Guest favorite
Barn in Virginia Beach
4.8 out of 5 average rating, 906 reviews

Cozy craftsman barn near the bay!

JoeiRating, 5 stars2 weeks ago
We stayed for 2 nights with our 3 dogs and everybody had a blast. The barn was very clean, cozy, and welcoming when we arrived. They had an essential oil diffuser on which made it smell lovely. There was a little binder left for us with everything we needed to know and some amazing sight seeing recommendations! The bed was comfortable and cooling/heating system worked great. Their stairs are a little steep and didn’t have runners so just keep that in mind with pets. Overall, this stay is perfect for 2 adults and their fur babies! Will definitely be booking again!
Top guest favorite
Cottage in Norfolk
4.97 out of 5 average rating, 324 reviews

Lovely Ocean View Cottage

JeromeRating, 5 stars1 week ago
We had such an enjoyable trip staying at this perfect cottage. The location was amazing-short walk to a tranquil beach that felt like our own little escape. The landscaping and yard were beautiful! The place felt like a peaceful retreat. The cottage itself was cozy, clean, and had everything we needed even a thoughtful welcome basket. It truly was the perfect getaway and just what we needed to recharge. Highly recommend!
Top guest favorite
Home in Williamsburg
4.97 out of 5 average rating, 220 reviews

Casita on the Corner

KathrynRating, 5 stars1 week ago
We had a great stay! The house was clean ans quiet, and the kitchen had all of the essentials you would need (spices, condiments, etc.). The house is close to all of the major attractions/downtown Williamsburg! The deck and fenced-in backyard were perfect for our toddler and pup!
Superhost
Home in Virginia Beach
4.89 out of 5 average rating, 132 reviews

Beach Home, Upscale Croatan Resort + Private Pool

BetsyRating, 5 stars3 months ago
This is a wonderful beach home within walking distance of the oceanfront. Our extended family enjoyed a fantastic visit. The house is set up perfectly for multiple families with a large gathering space on the top floor next to the kitchen. There are several decks throughout the home to catch the sea breeze and air. Beverly was a great host and responsive to our needs.

Family-friendly home rentals with a pool

Home in Cape Charles
4.77 out of 5 average rating, 78 reviews

Family Retreat, In-Ground Pool, plus Private Beach

AndrewRating, 5 stars8 months ago
This house and stay were exactly what we needed! We are a quiet family that loves peaceful spaces. The home was beautiful, well maintained, clean, updated, and extremely well appointed. Access to both the beach and lake was easy, as was getting into and out of town. Jack proactively reached out to us when we got there to ensure everything was in order and offered assistance if we needed anything. We didn’t need anything during the week but we felt good knowing he was available. We met some of the neighbors in passing and they were friendly and welcoming, too. Wonderful experience!
Top guest favorite
Home in Virginia Beach
4.99 out of 5 average rating, 81 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

NicholasRating, 5 stars2 weeks ago
Beautiful home in a wonderful location. Tanya was very friendly and communicative throughout the process.
Guest favorite
Condo in Virginia Beach
4.9 out of 5 average rating, 210 reviews

Oceanfront Gem VaB Studio Exceptional Views

terriRating, 5 stars3 days ago
This was better than expected. The condo was well appointed in all aspects, especially for a small space, it didn't feel small. location was perfect and views from this corner unit were amazing. I would absolutely stay here again.
Guest favorite
Guesthouse in Virginia Beach
4.72 out of 5 average rating, 115 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

John DavidRating, 5 stars3 weeks ago
He was so nice and everything!!
Apartment in Virginia Beach
4.65 out of 5 average rating, 136 reviews

Oceanview Queen & Sofa Bed, Kitchenette, Balcony-B

SabrinaRating, 5 stars6 days ago
This place felt very homey! My girlfriend and I enjoyed our stay and it was perfect! Will definitely be returning to this place when we go back to VA! I have a very large truck and parking wasn’t the most convenient but the lovely staff made sure we figured it all out. It was great!
Superhost
Home in Virginia Beach
4.84 out of 5 average rating, 124 reviews

Stunning Views of Back Bay & Seconds to the Beach

FrancescaRating, 5 stars2 months ago
What a beautiful and serene space for a women’s retreat! It is very obvious that the home is very well loved as well as very special. We all discussed coming back again because we enjoyed the space, the comfort and the scenery very much. We thoroughly enjoyed the great blue heron right outside the window each day as well as breathtaking sunsets. It was hard to get back to the grind after such a beautiful sanctuary weekend away.
Apartment in Virginia Beach
4.78 out of 5 average rating, 102 reviews

Virginia Beach Condo

RogerRating, 5 stars20 months ago
The location was great. Two streets walk to the boardwalk and two streets over to Neptune Statue on 30th Street. Supermarket for groceries was across the street from condo. The washer and dryer and dishwasher made everything so easy to keep up with. Keyless entry is perfect. There are many fun things to do in the area that is either a short walk or short drive. Examples are iFly indoor skydiving, parasailing, kayaking with dolphins, riding bikes/skateboards, mini-golf, etc. We had a great time!
Apartment in Virginia Beach
4.8 out of 5 average rating, 5 reviews

Luxury Beach Front Apartment

DanRating, 5 stars23 months ago
Jenna is a great host. Very responsive, personable throughout the process. Location is great. Right in the beach. Several restaurants are walkable. Beach here has a playground for the kids and a work out set up for those inclined. Pools and spa were great, especially on bad weather days.

Destinations to explore