Kid-friendly holiday rentals in Chesapeake

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Chesapeake

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Home

4.93 out of 5 average rating, 15 reviews

Incredible Location! Amazing Comfort!

Location, Location, Location!! Approximately 200 yards from your toes in the sand and the incredible blue Atlantic. A home away from home with all the amenities you could possibly need to make your stay, or extended stay a comfortable and memorable experience. The bunk room is ideal for an extended family or a comfortable room only for the little people. Virginia Beach has everything you need whether you're coming for vacation, relaxation, activity, or work. Experience Virginia Beach while stayi

Guest favourite

Townhouse

4.98 out of 5 average rating, 167 reviews

Oceanfront Getaway-Beach & Restaurants in VIBE!

Welcome to our cozy townhouse, your ultimate beach living experience! Just a short walk from the beach, our property is the perfect escape. Enjoy self-check-in, free bikes, surfboards, and games during your stay. With 6 comfy beds, (sleeps 8), equipped kitchen, a 65-inch TV, and high-speed internet. The central location is perfect for exploring Virginia Beach and Norfolk. We do not allow local guests within a 50-mile radius. Book now for an unforgettable beach getaway in our beautiful townhouse!

Guest favourite

Home

4.98 out of 5 average rating, 126 reviews

Family Reunion on the Bay

2020 prices through 2025! Unpretentious, clean & family-friendly. Bright open-plan home for easy living. Generous seating throughout. Loads of games, toys. Ideal for extended families. Side-door ramp, 1st-floor ADA bedroom, step-in shower w/seat & grab bar nearby. Backyard fire pit, picnic tables, grill, corn hole. Free firewood, propane, stand-up paddleboard, beach chairs & toys. IMPORTANT NOTES: 1. Absolutely NO PETS ALLOWED! ($750 fine) 2. Only weekly, Sat.-to-Sat. rentals June thru Aug. 30.

Superhost

Home

4.85 out of 5 average rating, 13 reviews

Sandy Shores Sanctuary #B | Next to beach

Welcome to Sandy Shores Sanctuary #B! Our charming 2 bedroom, 1 bath beach house is less than 10 min walk to the beach. Perfect for couples, families, or friends, this fully equipped home offers comfort and convenience. The cozy living area features plush seating, TV, and Wi-Fi. The kitchen is fully stocked. Bedrooms offer comfortable beds and storage. The clean, modern bathroom includes fresh towels and toiletries. Enjoy the patio or the backyard. Close to dining, shopping, and entertainment.

Superhost

Townhouse

4.92 out of 5 average rating, 111 reviews

Beach Livin' by the Chesapeake Bay - VA Beach

Beach livin' just a few short blocks to the Chesapeake Bay, Beach & great restaurants. New EVERYTHING! Tastefully decorated - all the amenities. 6 person farmhouse table. New deck-6 person table & chairs, grill. New privacy fenced backyard. Beachcart, chairs, towels, umbrella & sand toys. 2 queen beds & 2 bunk beds. Cozy livingrm w/loveseat, wicker chair, wicker swivel rocker, barstools, smart tv with basic cable. Apps avail. Base Rate includes 9% VA Beach occupancy tax and Lodging room tax

Guest favourite

Home

4.89 out of 5 average rating, 56 reviews

The Lemonade Stand on Plum with Backyard Bar

Welcome to 428 Plum Street, a large historic home built in 1920. Fully renovated in the spring of 2022. Located in the heart of historic Cape Charles, Virginia. Walk or cart anywhere in town from this ideal location. We are located just steps from Central Park and blocks to the Chesapeake Bay and all of the dining and shopping options along Mason Avenue. The home has 4 bedrooms, 2 full baths, a large front porch, and best of all a large fenced outdoor space with a full bar, tv and shower.

Guest favourite

Home

4.96 out of 5 average rating, 100 reviews

Cape Charles Retreat - 2 Blocks from Beach/Town

Welcome to Cape Charles Retreat! Come on up to the porch, grab a lemonade and settle into the porch swing for some much deserved rest and relaxation. Cape Charles Retreat is a beautiful 100+ year old American Foursquare located two blocks from the beach, Central Park, and town! Our home has been restored to preserve much of its original charm while adding modern amenities and outfitted with everything you’ll need for a great beach vacation. So grab your bathing suit and come for a visit!

Guest favourite

Home

5 out of 5 average rating, 6 reviews

Close to beach, ON Central Park

In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). This historic Parkside duplex has been recently renovated to include all the best amenities. This home sits ON the Cape Charles Central Park, giving you not only wonderful views of the park, but a perfect place for kids to run and play, families to walk, picnic and enjoy all the concerts and park festivals. It is also only two blocks to the beach and two blocks to the historic downtown – truly the best location!

Superhost

Home

4.92 out of 5 average rating, 182 reviews

Spacious home for up to 10! GREAT for families!

Welcome to the Vibe District in Virginia Beach! Exquisitely designed and spacious for up to 10 guests, you will not find a better location! Featuring 4 bedrooms, 3.5 bathrooms & 2 separate living rooms. This is ideal for a group! ~ Walking distance (just 1 mile) to the convention center ~ Easy walk to the beach- only 2.5 blocks! We provide a beach cart and gear for use! ~ Fully stocked kitchen ~ Full use of washer & dryer ~ High speed WiFi! Book your dream family getaway today!

Guest favourite

Cottage

4.97 out of 5 average rating, 236 reviews

Villa Positano

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Guest favourite

Tiny home

4.88 out of 5 average rating, 104 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

Guest favourite

Guest suite

4.99 out of 5 average rating, 289 reviews

*Charming 2BR *Patio *Prime Location *Family Fun!

Come relax in our charming guest suite! Perfect for families, we are minutes from the Jamestown Settlement, Colonial Williamsburg, Busch Gardens, and much more. The guest suite is attached to the main house, but has private entry, patio, driveway, and parking. The home sits on 2 acres, and is surrounded by majestic oak trees.