Family-friendly vacation rentals in Chesapeake

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chesapeake

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Virginia Beach

4.89 out of 5 average rating, 606 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Guest favorite

Rental unit in Virginia Beach

4.91 out of 5 average rating, 505 reviews

Private apartment only 3 blocks from the Beach

Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 500 mbps Wifi, internet tv. Futon-like couch.

Guest favorite

Condo in Virginia Beach

4.88 out of 5 average rating, 175 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Newly remodeled, stunning panoramic oceanfront views from the 3rd floor at the peaceful north end of Va Beach boardwalk. Perfect for two, this cozy 355 sq ft studio with wireless internet, large screen TV and full kitchen, has a community pool, back patio, charming beach lawn with tables & lounge chairs and is walking distance to outstanding restaurants, attractions and shopping. Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Guest favorite

Guest suite in Virginia Beach

4.98 out of 5 average rating, 294 reviews

Home away from home~Private,quiet, mins to bay

Home away from home is a spacious, comfortable, and private apartment with 1 Queen bedroom, full bath w/ tub, living area, work space, and fully equipped kitchen. Conveniently and centrally located in historic neighborhood: 3 mins to bay, 15 mins to oceanfront. We are within 4 miles of Norfolk Premium Outlets and IKEA, and are within 5 miles to Virginia Wesleyan and 15 miles to ODU. Walk to local favorite restaurants (New River Tap House, The Rustic Spoon, 1608 Crafthouse, Comfy Belly).

Guest favorite

Home in Virginia Beach

4.88 out of 5 average rating, 128 reviews

Half house w/pool & new patio all to yourself

PLEASE READ TO THE END!!!!!! Our home is close to restaurants, parks, the resort oceanfront and art and culture. You’ll love our place because of the location and the ambiance. Our space is good for couples, solo adventurers, business travelers or small families. Please know that my wife and I live in the other half of the house. There is NO shared space!!! You have a private entrance with full & private access to all amenities. Our home is LGBTQ+ friendly because LOVE IS LOVE!

Guest favorite

Condo in Virginia Beach

4.94 out of 5 average rating, 274 reviews

Beach Condo Block Off Boardwalk

Come enjoy everything Virginia Beach has to offer. Our condo has all of the comforts of home and accommodates 4 adults or perfect for families. Bedroom has a king size bed and living room has sofa that pulls out into a full size sofa bed. TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.

Guest favorite

Cottage in Norfolk

4.97 out of 5 average rating, 231 reviews

Positano Villa

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 favorite

Guest suite in East Ocean View

4.93 out of 5 average rating, 552 reviews

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

Guest favorite

Bungalow in Buckroe Beach

4.9 out of 5 average rating, 224 reviews

Bungelow by The Beach 2BR 1BA CABLE-Hampton, VA

5 Minute walk to the BEACH! 2 Bedrooms queen bed, 1 Bathroom, Living Room, Fully Equipped Kitchen, Dining Room, We have also provided an Adjustable Port-a-Crib. Washer/Dryer, dishwasher, Central AC & Heat, Front Deck, Gas Grill, Wireless Internet, Microwave, Kuerig & Coffee Pot, Silverware, Dishes, Pots and Pans, Games, Smart TV in both Bedrooms and Living Room, AND MORE! Pet policy case by case, 1 dog only, under 35 lbs $35.00 fee.

Superhost

Guesthouse in Chesapeake

4.86 out of 5 average rating, 170 reviews

Beautiful secluded 1BR apartment

Enjoy your home away from home! Drive into your personal garage above a private 1 bed 1 bath apartment in the beautiful Hickory area of Chesapeake. Perfect for business or vacation pleasure. Gorgeous updated kitchen with all the appliances you need. Comfortable and new queen size bed in the bedroom with the option of using the couch for additional sleeping space. A private washer and dryer for your use in the garage below apartment.

Guest favorite

Cottage in Virginia Beach

4.99 out of 5 average rating, 159 reviews

The Beach Nest. Walk to oceanfront.

The Beach Nest is a pristinely clean cottage located just a half-mile walk from the oceanfront and boardwalk. The cottage is well-outfitted with beach chairs, beach cruisers, beach towels, a beach cart, and a sand umbrella. A quaint retreat ideal for two. The Beach Nest is NOT a party house. SMOKING IS PROHIBITED. PETS ARE NOT ALLOWED as we often host guests with allergies.

Guest favorite

Home in Chic's Beach

4.96 out of 5 average rating, 127 reviews

Water Oaks at Chic's Beach

Bright, airy beach home across the street from the Chesapeake Bay beach, a quarter mile east of the Chesapeake Bay Bridge-Tunnel . . . 1600 sf, 3 br, 2.5 ba . . . eclectic residential neighborhood . . . diverse restaurants and a convenience store within easy walking distance . . . five-minute drive from more comprehensive shopping and fifteen minutes from VB oceanfront.