Kid-friendly vacation rentals in Chesapeake

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Chesapeake kid-friendly rentals

Kid-friendly house rentals

The exterior of a single-story home features a brick facade complemented by white paneling. A covered entryway protects the front door, and well-maintained landscaping with small plants and a pathway leads up to the entrance. Windows allow natural light to enter the interior.
Home in Chesapeake
4.76 out of 5 average rating, 62 reviews

Southern Charm Warm and Welcome

BenitaRating, 5 stars1 month ago
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!
Top guest favorite
A bright living area features a large flat-screen television mounted on the wall and a comfortable seating arrangement. Large sliding doors open to a view of the water outside, while a soft area rug adds warmth to the space.
Home in Portsmouth
4.95 out of 5 average rating, 60 reviews

R & R River House

EvanRating, 5 stars1 week ago
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.
Superhost
A modern kitchen is highlighted by a spacious island featuring four wooden bar stools. Natural light filters through sheer curtains, illuminating the sleek cabinetry and white countertops. A stylish centerpiece is positioned on the island, complementing the contemporary design.
Home in Chesapeake
4.93 out of 5 average rating, 57 reviews

Chesapeake Haven - Relaxing Space + Lux Kitchen

JoshuaRating, 5 stars2 weeks ago
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!
Guest favorite
A modern kitchen features stainless steel appliances, including a refrigerator and microwave. White cabinetry provides ample storage, while granite countertops add a touch of sophistication. Large windows allow natural light to brighten the space, complemented by a sleek, dark stove and dishwasher.
Home in Portsmouth
5 out of 5 average rating, 6 reviews

Comfortable Portsmouth Classic

AliciaRating, 5 stars2 weeks ago
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
Guest favorite
A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.
Home in East Ocean View
4.92 out of 5 average rating, 193 reviews

@Whit’s End? Come in and Relax

CaraRating, 5 stars1 week ago
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.
A two-story brick house features a prominent entryway with an arched doorway. Lush greenery surrounds the home, and well-maintained flower beds border the pathway leading to the entrance. The front yard is gently sloped, complementing the home's elegant design.
Home in Chesapeake
4.58 out of 5 average rating, 26 reviews

Michael’s Luxury Home

robertRating, 5 stars3 months ago
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.
Guest favorite
A modern living room is presented, featuring a spacious sectional sofa with light fabric. A wall-mounted smart TV dominates the area, and a glass coffee table is placed in front. Two black bar stools are positioned near a kitchen counter in the background, enhancing the open layout.
Home in Portsmouth
4.91 out of 5 average rating, 11 reviews

Home Away From Home

EricRating, 5 stars2 months ago
Place was as described and all info was given and easy to understand definitely worth staying if your in that area
Top guest favorite
A single-story bungalow features a welcoming brick exterior, surrounded by well-maintained landscaping. A spacious driveway leads to the house, which is framed by tall trees. The front porch, adorned with white railings, provides an inviting entryway. A detached garage is visible in the background.
Home in Portsmouth
5 out of 5 average rating, 12 reviews

Cornick Corner near "Rivers Casino"

JuanRating, 5 stars2 weeks ago
Everything was great!

Kid-friendly apartment rentals

Guest favorite
A bright guestroom is furnished with two double beds, each featuring a light-colored quilt. Nightstands with lamps are positioned beside the beds. A large window offers views of greenery, with soft curtains complementing the decor.
Apartment in Williamsburg
4.95 out of 5 average rating, 111 reviews

Comfy 1BR w pond view Kingsmill

AmandaRating, 5 starstoday
Super safe and beautiful gated neighborhood. Gorgeous setting. Quick drive to all things Williamsburg. Thanks so much, Lisa!
Guest favorite
A cozy living area features a light-colored sectional sofa with decorative pillows, positioned adjacent to a round coffee table on a soft area rug. Large windows adorned with sheer turquoise curtains allow natural light to fill the space, complemented by a ceiling fan and wall-mounted television.
Apartment in Phoebus
4.92 out of 5 average rating, 118 reviews

Getaway Minutes from the Beach

SherranRating, 5 stars1 week ago
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.
Superhost
A spacious bedroom is depicted, featuring a large bed with a light-colored blanket. A ceiling fan is installed above, and large windows are dressed with dark curtains. A couch and a small table with a chair are positioned to the side, contributing to the room's layout.
Apartment in Buckroe Beach
4.89 out of 5 average rating, 120 reviews

Sojourn Guest House: Buckroe Beach Suite B

MaddyRating, 5 stars1 week ago
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.
Guest favorite
A wooden deck is showcased, surrounded by lush greenery. The railing is made of wood with black metal accents. The space offers an inviting outdoor area, nestled in a tranquil environment with a view of trees and a fenced yard.
Apartment in Virginia Beach
4.91 out of 5 average rating, 538 reviews

Private apartment only 3 blocks from the Beach

MacKenzieRating, 5 stars1 week ago
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!
Guest favorite
The exterior of a historic home features classic architectural details, including a covered porch with white columns. An American flag is prominently displayed, and mixed flower pots are arranged on the brick pathway. Large windows allow for natural light, showcasing the home’s inviting presence.
Apartment in Olde Towne
4.96 out of 5 average rating, 118 reviews

Best location in Olde Towne Portsmouth

AnnaRating, 5 stars3 weeks ago
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 :)
Top guest favorite
The private room features a spacious bed draped with a textured blanket, accompanied by a cozy armchair and an accent chair. A decorative fireplace is situated under a wall with circular art pieces. Natural light filters through the window, enhancing the room's warm tones.
Apartment in Olde Towne
4.98 out of 5 average rating, 110 reviews

English Basement Hide-Away

KevinRating, 5 stars2 weeks ago
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.
Top guest favorite
A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.
Apartment in Newport News
4.98 out of 5 average rating, 203 reviews

Centrally Located Sleek Studio Apartment

KaylaRating, 5 stars2 days ago
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!
Top guest favorite
A fully stocked kitchen is presented, featuring a gas stove, a refrigerator, and a microwave. A dark wooden hutch displays dishes and glassware, while a Keurig coffee maker is located on the countertop. Natural light filters in through a nearby window, illuminating the tiled floor.
Apartment in Olde Towne
4.96 out of 5 average rating, 280 reviews

Cozy Ground Floor Apt in Historic Home

LisaRating, 5 stars4 days ago
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

Top guest favorite
A modern living room features a gray sofa adorned with decorative pillows, paired with a light blue coffee table. Two lamps provide ambient lighting. Artwork of coastal scenes decorates the walls, while a patterned area rug enhances the room's coastal theme.
Condo in Virginia Beach
4.99 out of 5 average rating, 108 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

AngelaRating, 5 stars2 weeks ago
Great place, just as advertised. thanks for everything, Samantha!
Top guest favorite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Condo in Williamsburg
4.95 out of 5 average rating, 164 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

AmyRating, 5 stars4 days ago
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!
Guest favorite
A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.
Condo in Virginia Beach
4.9 out of 5 average rating, 221 reviews

Oceanfront Gem VaB Studio Exceptional Views

GingerRating, 5 stars1 week ago
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!
Superhost
The living area features a light-colored sofa positioned across from a modern coffee table. A bar area with two stools is visible in the background, leading to a kitchen with white cabinetry. Natural light illuminates the space, creating a bright and open atmosphere.
Condo in Virginia Beach
4.84 out of 5 average rating, 136 reviews

Beach Bungalow on the Boardwalk

KimoraRating, 5 stars1 month ago
Beautiful home! Very close to the beach and boardwalk. Overall we had a pleasant stay!
Guest favorite
A well-furnished living room is depicted, featuring a dark blue couch adorned with patterned throw pillows. Two abstract art pieces hang above, and a flat-screen television is mounted on the wall. Light is provided by a table lamp, creating a bright and inviting space.
Condo in Newport News
4.89 out of 5 average rating, 160 reviews

*Mid/Long Term Rental* Cozy Home at Mary Roberts

CalebRating, 5 stars1 month ago
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.
Guest favorite
A bright and airy living space features a gray sectional sofa and a matching armchair, providing seating options. A white dining table with blue chairs occupies one side, and a flat-screen TV is mounted on the wall. Light enters through multiple window panes, accented with white shutters.
Condo in Virginia Beach
4.93 out of 5 average rating, 290 reviews

Beach Condo Block Off Boardwalk

JasonRating, 5 stars3 weeks ago
Great property and location along with responsive host.
Guest favorite
A wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.
Condo in Sandbridge
4.87 out of 5 average rating, 237 reviews

Ocean Escape

JamesRating, 5 stars4 days ago
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+
Guest favorite
A well-equipped kitchen and dining area are visible, with modern appliances and a stylish table set for six. A comfortable sofa in the living space is complemented by a soft area rug, enhancing the inviting layout. Natural light is allowed in by the open layout.
Condo in Virginia Beach
4.91 out of 5 average rating, 323 reviews

2 bedroom condo with oceanfront one block away!

KarlaRating, 5 stars1 day ago
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