Family-friendly holiday rentals in Hampton Roads

Guesthouse at Vessel Farm & Winery, Waterfront

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Family · Indoor spaces · Decor

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!

Kitchen · Indoor spaces · Sleep quality

"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!

Kitchen · Family · Access

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach

Welcome To Our Place! Ideal For Family Trips, Traveling For Business, Staycations Or Baecations In The Downtown Hampton Area. The Home (Unit A) Is Equipped With Complimentary WiFi, 65” Smart TV, Fully Stocked Kitchen, Coffee Bar, Washer & Dryer! Walking Distance To Restaurants & Nightlife! 5 Min: Buckroe Beach Fort Monroe Hampton University 15 Min: Norfolk International Airport Norfolk Premium Outlets 25 Min: Busch Gardens Williamsburg Water Country USA Virginia Beach Oceanfront

Indoor spaces · Kitchen · Location

4BR Oasis: Your Home Away

Uncover the allure of our 4-bedroom retreat, steps from dining and entertainment. Thoughtfully designed with a fully equipped kitchen, inviting living spaces, and an amazing master bedroom. Proximity to Buckroe Beach, Busch Gardens, Boo Williams Sportsplex, Hampton Waterplex, and the historic charm of Williamsburg awaits your adventure. Let us tailor your stay with personalized recommendations. Welcome to your expansive haven, where every corner is crafted for your enjoyment!

Family · Kitchen · Pool

Family Holiday House. Events and Beaches Nearby

Large comfy 5BR/3BA home in established neighborhood w/Roku TV & high speed internet! Near Buckroe Beach, Hampton Coliseum Event Center, NASA, Langley Air Base, Boo Williams Sports Arena and Newport News. Also near Virginia Beach, Williamsburg and Busch Gardens There are many parks for recreation. We have a large enclosed porch for lounging. The front entry has an easy wheelchair ramp. Restaurants galore and endless shopping. NEAR AIRPORTS in Newport News and Norfolk.

Kitchen · Indoor spaces · Hospitality

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Kitchen · Family · Condition

Stylish Beach House, Hot Tub, Pet Friendly

Welcome to your coastal oasis of relaxation & fun. Enjoy beach fun, hot tub & games in a modern open concept living space. This stylish, pet friendly home away from home is perfect for families. It's 1.5 blocks from the beach. This charming SFH offers 2 bedrooms, loft, chef's kitchen, game room, spacious backyard with deck, hot tub, fire pit, BBQ grill, & volleyball/badminton court. It's centrally located near VA Beach, Williamsburg, & Downtown Norfolk.

Indoor spaces · Family · Value

The Pines- Family Entertainment Room

This ranch home is located in a quiet & safe neighborhood (Windy Pines) in an area we call “Churchland”. The area is comprised of tri-cities in the same area. (Portsmouth, Chesapeake & Suffolk) Near military installations, shipyards, hospitals, beaches, amusement parks, museums, casinos, and more Property is walking distant from Hoffler Creek Wildlife Preserve nature trail and less than a mile from Popular Harbour View Shopping area.

Kitchen · Family · Beach

Life on a Sandbar right on Chesapeake Bay

Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!

Kitchen · Family · Cleanliness

4BD home w/ game room & pool near Langley & PTC!

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!

Indoor spaces · Kitchen · Outdoor spaces

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.

Indoor spaces · Kitchen · Decor