We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Family-friendly holiday 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

Home

4.84 out of 5 average rating, 121 reviews

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

Guest favourite

Apartment

4.92 out of 5 average rating, 127 reviews

Walk to beach BEAUTIFUL 2BR 1BA condo

1 block to Ocean/Boardwalk on 9th and Pacific in the heart of resort town. Beautifully furnished, 600sq ft beach-themed condo. Beds sleep 4 (1 Q, 2 Twin) and comfortable sleeper sofa adds 2 more. Also close to Convention Center, Vibe District, new Sports Complex. Perfect for family w/children or 4 adults. Free parking for 2 cars - 1 on front of unit and 1 in covered garage across condo. Spend a min 2 nights Sept-May and stay a week from early June to Labor Day (summers days are Sat-Sat rental).

Guest favourite

Home

4.85 out of 5 average rating, 227 reviews

Home Away from Home! A+Location, Clean, Great Yard

Remodeled kitchen and bath. Discounts for longer stays. The entire house and yard is yours. Close enough so you can walk or bike to shopping and restaurants, or head to the beach about 2.5 miles away. Internet and a work desk, comfy beds with cotton sheets provided. There is a back porch, large fenced yard, BBQ grill, fire pit. Rules for booking our home- no pets are allowed. We require our guests have good AirBnb reviews. Self check in- we ask that you message us when you have arrived.

Guest favourite

Flat

4.96 out of 5 average rating, 379 reviews

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

Guest favourite

Apartment

4.94 out of 5 average rating, 275 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 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

Home

4.79 out of 5 average rating, 143 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $100 pet fee with pre approval. Starting June 25th 7 night min check in on Friday only !

Guest house

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 favourite

Townhouse

4.91 out of 5 average rating, 114 reviews

Family Friendly Condo just 3 blocks to the beach!

Family friendly condo just a short walk to the beach. Blocks from the Virginia Beach Sports Center, Convention Center, Dome, and Wave Garden (opening June 2025)! Perfect spot for those visiting for tournaments and events in Virginia Beach or groups looking for a beach vacation! Walk to great restaurants, breweries, fun stores and surf shops. Check out the Farmer's Market on Saturday mornings.

Guest favourite

Cottage

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 favourite

Home

4.9 out of 5 average rating, 364 reviews

Pet friendly 3 bedroom beach house

Completely remodeled in 2021. 3bedrooms 2.5 bath Less than a mile to ocean. Ranch house, deck out back , large fenced yard. Large kitchen, easy parking close to the beach. Close to oceanfront, boardwalk, restaurants, whole foods, trader joes, target, walmart etc No parties, events, or gatherings, only 9 people allowed at house at any time.

Guest favourite

Flat

4.98 out of 5 average rating, 125 reviews

Yorktown on the Waterfront

Overlooking Wormley Creek in historic Yorktown, enjoy the privacy of an apartment within a beautiful home with amenities unlike any other. Full kitchen, washer/dryer, theater room, fireplace, 2 full baths and separate private entrance and security system. Outdoor living area with grill, dock and privacy.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Chesapeake family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Cottage

4.88 out of 5 average rating, 144 reviews

Horses-Views-Dog Friendly-4WD Area

Holiday home

5 out of 5 average rating, 4 reviews

1 Block to the Beach, Indoor Pool Great 4 Kids

Apartment

4.71 out of 5 average rating, 7 reviews

VA Beach Oceanfront - Only available 6/14-21, 2025

Flat

4.75 out of 5 average rating, 4 reviews

Ocean Key 2 Bdrm Across the Street from the Ocean

Apartment

4.77 out of 5 average rating, 13 reviews

King's Creek Plantation: 3-BR, Sleep 10, 2 Kitchen

Home

4.72 out of 5 average rating, 18 reviews

Family 4x4, Beach, Pool, Hot Tub, Theater, Sun-Sun

Family- and pet-friendly home rentals

Guest favourite

Home

4.96 out of 5 average rating, 128 reviews

Water Oaks at Chic's Beach

Guest favourite

Guest suite

4.89 out of 5 average rating, 609 reviews

Quiet Neighborhood 7 Miles From the Beaches

Guest favourite

Home

4.99 out of 5 average rating, 78 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

Home

4.57 out of 5 average rating, 137 reviews

Buckroe Beach Affordable for 4 -Walk to the Beach!

Guest favourite

Guest house

4.73 out of 5 average rating, 99 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

Guest favourite

Barn

4.8 out of 5 average rating, 892 reviews

Cozy craftsman barn near the bay!

Guest favourite

Cottage

4.97 out of 5 average rating, 309 reviews

Lovely Ocean View Cottage

Home

4.89 out of 5 average rating, 131 reviews

Beach Home, Upscale Croatan Resort + Private Pool

Family-friendly home rentals with a pool

Home

4.77 out of 5 average rating, 78 reviews

Family Retreat, In-Ground Pool, plus Private Beach

Home

5 out of 5 average rating, 6 reviews

Beach Life is Good!

Campervan/Motorhome

4.72 out of 5 average rating, 50 reviews

Lil' 60's SCOTTY/Best Spot in VIRGINIA BEACH!!!

Guest favourite

Apartment

4.88 out of 5 average rating, 179 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Flat

4.64 out of 5 average rating, 133 reviews

Oceanview Queen & Sofa Bed, Kitchenette, Balcony-B

Guest favourite

Apartment

4.95 out of 5 average rating, 203 reviews

Sea La Vie! Home Away From Home.

Flat

4.8 out of 5 average rating, 5 reviews

Luxury Beach Front Apartment

Apartment

4.83 out of 5 average rating, 53 reviews

Seas The Day of Virginia Beach

Quick stats about holiday rentals that are family-friendly in Chesapeake

Total rentals
450 properties
Total number of reviews
15K reviews
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
270 properties have a dedicated workspace
Wifi availability
440 properties include access to wifi

Destinations to explore