
Kid-friendly holiday rentals in Chesapeake Beach
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Top-rated kid-friendly rentals in Chesapeake Beach
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Popular amenities for Chesapeake Beach kid-friendly rentals
Child-friendly house rentals

Wander Cape Charles
second time staying here and it was better than i remembered. the house itself is incredible.. huge kitchen island for entertaining, immaculate bedrooms, and that back window wall is just spectacular. 10/10 vibes, love this place!

941 Coastal Luxury Retreat
It was a great place to stay! Super clean and comfortable. Many great places with if walking distances or a short drive. The farmer’s market is a must do! Carrie was super helpful with a question during the stay. We would stay again!

10 min to Ocean View: BBQ | Volleyball| Fire Pit
Exactly as advertised! Nice home in a great location near the beach. Francisco was very responsive, seemed like he replied immediately every time I reached out. Home was clean, quiet, and ideal for my short stay. Enough space for a small family or a few friends visiting the area. Would absolutely consider this home on my next visit to Norfolk!

The Blue Octopus~Private Pool~HotTub~Beach~FirePit
Family vacation for almost a week and everyone loved it! We definitely recommend families to come to the Blue Octopus for their next visit to Ocean View-Willoughby Spit. Friendly, clean and with all the amenities for the whole family.

Paint The Beach Pink! Full House | Private Pool
This place is so amazing from the way its decorated to how clean everything is in every room..it has anything and everything you would need for the beach or in the beach house and a quiet neighborhood i will definitely be staying here again 😊

@Whit’s End? Come in and Relax
Whit’s end was a wonderful vacation for my family. Perfect size place for my family of 6. Very short walk to the beach where we spent most of our time. Felt like we had the whole beach to ourselves which I loved. Nice playground very close by. Farmers market on Saturday which was very popular. Golf course 2 miles away that my husband and boys explored. Also a brewery in the neighborhood that was a nice bonus.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
I could not wait to write a review about our stay. So much so that we are not even home yet. We had a glorious week at Bay Bliss! Bliss is the perfect description. Anywhere in this beautiful home you can hear the waves of the ocean. There was nothing better than listening to that while falling asleep on the comfiest bed in the master bedroom. Hosts were extremely responsive, helpful with local recommendations and extremely friendly. I have stayed at lot of AirBnb’s and hotels. Honestly, I have never felt so at home and I felt that way from the second I walked in the door. We will definitely be back.

The Seaglass Cottage
The host was so kind and made sure we had a comfortable stay! The AC ended up not working due to an accidental mishap when she was working on her yard! She was able to get the AC fixed as we arrived to the Air BNB and we had the coolest room ever ( which we love) especially on a hot day! We are thankful for the time she took to get that done ASAP! She also had a wonderful cute cottage with all that you’d need for a short stay! It was equipped with great dishes and all the things you’d need for a perfect stay in a home :) it was extremely clean and decorated nicely for your small family! It also has a beautiful back yard oasis to sit out and relax or go for a swim :) you won’t want to miss this Airbnb!! Located near the beach and a great park and walking paths for you kiddos!! All you need nearby just a short walk away!! It was a great getaway for the weekend with a very kind host who is always there to help if needed :)
Kid-Friendly apartment rentals

Comfy 1BR w pond view Kingsmill
Great place to stay away from lots of people. Super quiet and neat.

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Leo’s Airbnb was GREAT. He was extremely responsive and helpful. Had great recommendations for places to grab a bite to eat. The Airbnb itself was great, quiet, and clean. I would definitely suggest booking with him!

Getaway Minutes from the Beach
I come home every year to visit with my family members. I will no longer be staying in those hotels on Mercury Blvd. Conveniently located. Everything you need for cooking in the cabinets. Coffee on deck. Beds were very comfortable. Laundry room was good. Air conditioning was on point. I love hot water awesome. See you in August.

Sojourn Guest House: Buckroe Beach Suite B
Seamless, easy, clean. The location was perfect for us with easy access to the beach and major roads. Our stay here was amazing and simple.

Private apartment only 3 blocks from the Beach
We loved this space! We stayed the night for a concert in the area and were able to walk to and from the venue which was awesome! We got to the space and everything was very nice and felt like home! Would definitely recommend and stay here again!

Best location in Olde Towne Portsmouth
I happened to be visiting during a holiday weekend while lots of events were happening in the downtown that I didn’t know about, and they were all just a short walk from this place! I would absolutely stay here and visit Portsmouth again :)

English Basement Hide-Away
Its a nice cozy spot thats right by the water with plenty of restaurants to check out near by. A majority of them are walkable distances. There is also easy access to the highway if needed to travel further out. The area is very quiet with almost no noise. Surrounded by a community of families so you'll quickly feel right at home.

Centrally Located Sleek Studio Apartment
My husband and I visited Steff's AirBnB on our Honeymoon and were beyond pleased! She provided so much for her guests, including eggs and bacon for breakfast!! Her space was so clean and welcoming. It was the perfect, quiet spot for us. I found the bed to be a little too firm for my personal taste, but I still got a decent enough night sleep and I will absolutely be back if we come down to Williamsburg again. The backyard was so adorable and peaceful! I only wish the weather would have been better to enjoy the fire pit and smores kit!! Thank you Steff for having us!
Child-Friendly Holiday Condos

Beautiful Beachfront Condo
The only issue we had was our code for the building and parking did not work at first! Pam was very quick to resolve! There are no elevators in parking garage, I would take my stuff in at the entrance and then park! Dolphin run staff was not much help! We had a second car that we were supposed to get a parking permit for. They just told us to park and not worry about signs that clearly stated towed with no permit. Our car did NOT get towed!

Tropical 2BR Condo Getaway 1 Block from the Beach!
Great place, just as advertised. thanks for everything, Samantha!

2 Bedroom Condo One Block from the Oceanfront!
This condo was the perfect size for our family of three. It was awesome to be able to cook a few meals during our trip. This was in the perfect location, less than a 5 minute walk to the beach. We were able to walk to the fishing pier and the Rudee Inlet easily. We loved how the condo was decorated too. Our host was wonderful! Very helpful and responsive!

Oceanfront Gem VaB Studio Exceptional Views
This was our second time staying at one of Rebecca and Sean’s VA Beach condos — and the experience did not disappoint! This is just a perfect location, at the very end of the Boardwalk, with a private grassy lawn and outdoor seating just for the condo residents. Lots of restaurants in the surrounding blocks. Our favorite thing is the view — you look right out onto the ocean from the patio, and you can see the beach and the sunrise from the comfortable bed each morning. We spent unhurried hours sitting on the patio in the evenings enjoying the sound of lapping waves and the night sky. This cozy studio was just right for the two of us. Highly recommend. I’ve no doubt we’ll stay there again in the future!

Oceanfront, beach, boardwalk, fun, dolphin, sunris
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

Beach Bungalow on the Boardwalk
Beautiful home! Very close to the beach and boardwalk. Overall we had a pleasant stay!

Beach Condo Block Off Boardwalk
Great property and location along with responsive host.

Ocean Escape
My family really enjoyed our vacation. It was a great location to the beach and a private pool. It was our first vavation w/ an 18month old and 1 on the way. Randy was very quick to respond to any questions. A+
Destinations to explore
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach