Family-friendly vacation rentals in Chesapeake

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).

Family Reunion on the Bay

Unpretentious, clean & family-friendly. Bright open-plan 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. 3 IMPORTANT NOTES: 1. bedrm #5 reduced to 4 beds in 2026 2. Absolutely NO PETS ALLOWED! ($750 fine) 3. Only 7-day Sat.-to-Sat. rentals June thru Aug. 30.

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 and you can walk to the beach is 3 minutes or less! Come have a relaxing and fun vacation at the beach.

Pet friendly 3 bedroom beach house

Welcome to your perfect vacation getaway! This remodeled 3-bed, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. Bedrooms are equipped with comfy beds. Pet-Friendly: The spacious backyard and deck are perfect for playtime and relaxation. Great location close to shopping and restaurants. You’ll feel right at home in this safe neighborhood. Please note: No parties. Only 9 people are allowed at the house at any time

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.

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 !

Charming house close to beach and shops!

Uncover Cape Charles' enchanting charm at Heron House. This stylish retreat suits couples, small families, or friends looking for a delightful getaway. Enjoy the private backyard, stocked kitchen, and all amenities for beach fun, fishing, kayaking, shopping, and more. Recharge in this cozy haven with beach chairs, umbrellas, and adult bikes. Your ultimate beachside escape is here! Non-Smoking & Pet Free

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.

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.