Family-friendly holiday rentals in Virginia Beach

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.

Indoor spaces · Family · Layout

*NEW* Spacious/Standalone 4BR Beach House

Bring the whole family to The Breaker House and enjoy this luxury beach home that sits just 4 blocks from the Virginia Beach Oceanfront and 2 blocks from the Convention Center. Located in the trendy Vibe District, this home is also walking distance to Virginia Beach's best breweries, restaurants, and bars! Walk or bike to everything! This property is a 4BR/3.5 BA three story home (1 King, 2 Queen, 2 Twin, 1 Futon) with premium amenities. The perfect spot in VB to gather as family or friends!

Kitchen · Family · Barbecue

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Indoor spaces · Kitchen · Quiet

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

Kitchen · Indoor spaces · Decor

Artful Retreat with a Private Pool

Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!

Family · Indoor spaces · Condition

Oceanfront-Dome/Wavegarden-VIBE Restaurants/Beach

Cozy townhouse by the beach, short walk to the sand and 5 min walk to Wavegarden at Atlantic Park Surf Park! Enjoy self check-in, 2 free bikes, surfboards, full kitchen, 65” TV, fast Wi-Fi. Sleeps 7 (6 beds). Central to Virginia Beach & Norfolk; stroll to cafes & fun. Ask about discount for months stay. Free parking, washer/dryer, beach chairs, beach cart, and a quiet patio. Walk to the boardwalk & dining. Family-friendly; & starter coffee provided. Book your beach getaway

Family · Kitchen · Location

Cher's Place @ The Beach

Relax with the whole family at this peaceful place to stay in Sandbridge! This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture and bedding so pics may not match perfectly. Need more room?? See my other property!

Indoor spaces · Kitchen · Parks

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.

Kitchen · Indoor spaces · TV

Designer Beach House | Pool, Hot Tub, Walk to Sand

Breaker Bay is a fully renovated 5BR, 3BA beach cottage in the heart of Sandbridge. With a private pool, hot tub, spacious deck, and open living space, it’s perfect for families or groups. Just minutes from the sand, it offers the ideal blend of comfort and coastal charm. Wake up to ocean sunrises, unwind with bay sunsets, and enjoy all that this peaceful beach community has to offer. Your perfect coastal getaway starts here.

Family · Kitchen · Accuracy

Vibe District • Near Beach • Balcony • Sleeps 6

Stay in the heart of Virginia Beach’s Vibe District in this stylish townhome 🌊 Located near the upcoming Atlantic Park and just minutes from the beach, you’ll be surrounded by top restaurants, breweries, and local attractions. Enjoy a comfortable layout, private balcony for sunsets, and all the essentials for a relaxing stay. Perfect for couples, families, or small groups looking for a vibrant coastal getaway.

Kitchen · Family · Comfort

Chic’s Beach Oceanfront 3BR Home With Deck Views

🌊 Direct beachfront location at Chic’s Beach 🌅 Ocean views from all 3 levels 🏡 Spacious 3BR home sleeps up to 8 🛏️ King, 2 Queen beds + twin-over-full bunk 🌴 Multiple private decks for relaxing outdoors 🍳 Fully stocked kitchen for easy meals 🛋️ Open living area perfect for gathering 📶 Fast Wi-Fi + Smart TVs throughout 🧺 In-home washer and dryer 🚶 Walk to local dining and beach favorites

Indoor spaces · Family · Decor

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.

Family · Indoor spaces · Layout