
Kid-friendly vacation rentals in Chesapeake
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Chesapeake
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake kid-friendly rentals
Kid-friendly house rentals

Southern Charm Warm and Welcome
I had an amazing stay at Annette’s place! The house was spotless, and the bed was incredibly comfortable. I felt right at home and enjoyed every moment. The basketball and hoop were a bonus for my athlete! Highly recommend to anyone looking for a cozy and clean place to stay!

R & R River House
Overall this was a great experience, & even with the max amount of guests (6 total) we generally had a lot of space; places to sit & relax; & all felt very comfortable. The view of the lake was also incredible & the amenities provided were top notch. The only criticism I would give is that the listing seems a little misleading about the building being a standalone house vs the town home/condo style house that it actually is. This wasn’t a huge issue but it seems fair to note as the parking was a little confusing once we realized that it was a town house with a parking lot, rather than a standalone one with a driveway. To be fair we did have the max amount of guests & according to Jason this was out of the norm; & Jason did do his best to communicate in finding places to park- but I feel that if there’s any hesitation he might have of that many people being there then the listing may need to be made more clear. Overall though we had a great time & enjoyed the view most of all.

Chesapeake Haven - Relaxing Space + Lux Kitchen
My family and I had a wonderful stay at this lovely Airbnb! The house was spotless, cozy, and felt just like home. Everything was thoughtfully prepared, from the comfortable bed to the little touches that made the space warm and inviting. The host was kind and responsive, making the whole experience easy and relaxing. I’d definitely stay here again—highly recommend!

Comfortable Portsmouth Classic
A nice private space with a wonderful large smart TV, good quality washer and dryer that is convenient and a nice kitchen. It's basically an old bungalow home upgraded or modernized, decked out. Friendly neighbors. It's quiet at night

@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.

Michael’s Luxury Home
It is a beautiful house. Nice pool and backyard. We stayed here in the winter time while our son had a wrestling tournament in Virginia Beach, but this would be a great place to stay in the summertime with the great pool and backyard.

Home Away From Home
Place was as described and all info was given and easy to understand definitely worth staying if your in that area

Cornick Corner near "Rivers Casino"
Everything was great!
Kid-friendly apartment rentals

Comfy 1BR w pond view Kingsmill
Super safe and beautiful gated neighborhood. Gorgeous setting. Quick drive to all things Williamsburg. Thanks so much, Lisa!

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!

Cozy Ground Floor Apt in Historic Home
Dottie's place was a quiet oasis just away from the bustling downtown area. Super walkable to museums, a view of the shipyard and great bars restaurants and coffee shops. The apartment was just as described and super clean. Dottie provided all the appliances you would need for a great stay and snacks! We would stay again and highly recommend this place!
Kid-friendly condo rentals

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

Kingsmill 1bed/1ba on Golf Course 9th Fairway
Crystal's condo was spotless and an easy place to stay. Crystal was very proactive and made us feel welcome. her dinner suggestions were superb too! perfect for a weekend getaway in a resort atmosphere. Thank you so much, we highly recommend!

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!

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

*Mid/Long Term Rental* Cozy Home at Mary Roberts
Nickie's place was excellent for our family of 4 adults and 1 toddler. It had all of the amenities we needed for a relaxing 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+

2 bedroom condo with oceanfront one block away!
Love the stay in the VA beach condo! Host was very accommodating and friendly, would love to come back!
Quick stats about vacation rentals that are kid-friendly in Chesapeake
Total rentals
130 properties
Nightly prices starting at
R541 ZAR before taxes and fees
Total number of reviews
7.3K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Virginia Beach Vacation rentals
- Williamsburg Vacation rentals
- Richmond Vacation rentals
- Shanghai Vacation rentals
- Myrtle Beach Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- Rentals with pools Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Family-friendly rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Beachfront rentals Chesapeake
- House rentals Chesapeake
- Waterfront rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Apartment rentals Chesapeake
- Condo rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Cottage rentals Chesapeake
- Rentals with a washer and dryer Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with beach access Chesapeake
- Kid-friendly rentals Virginia
- Kid-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Kiptopeke Beach
- Little Creek Beach
- Golden Horseshoe Golf Club