Planning a group trip to Virginia Beach? Whether you’re hosting a wedding weekend, gathering your extended family, or coordinating a sports team’s travel, Transcendent Stays offers the perfect vacation rentals for large groups in Virginia Beach. With a mix of boutique charm and group-friendly homes—some even located side-by-side—you can stay connected while enjoying the comfort and space every group needs. Looking for large group vacation ideas? Start with our top properties for memorable group gatherings:
The Inn at Old Beach
Boutique Hotel Just Blocks from the Oceanfront
The Inn at Old Beach is a guest favorite for wedding parties, reunions, and small retreats. With 9 beautifully designed rooms, guests can get the hotel setup with a homestyle feel. The inn has inviting shared spaces, including breakfast area and hot tub space—this restored historic inn offers the warmth of a bed & breakfast with the elevated design of a boutique hotel.
Just a few blocks from the Virginia Beach Boardwalk and oceanfront, it’s the perfect home base for guests who want to stay under one roof while still having walkable access to the beach, coffee shops, and restaurants. Ideal for those seeking vacation rentals for large groups with charm and character, The Inn at Old Beach is the perfect place to gather and make memories—whether you’re sipping coffee on the porch or hosting a pre-wedding toast in the cozy lounge.
25th Street Homes
A Row of Homes Designed for Connection and Comfort
Another fantastic setup for groups is our collection of homes on 25th Street. With four houses in a row, each sleeping 8–12, these homes are perfect for multiple families or sports teams looking for vacation rentals for large groups. Located right across the street from the Inn at Old Beach, they offer a variety of options for groups.
Each home is thoughtfully decorated and fully stocked with everything you need—from kitchen essentials to comfy living rooms. Walk to the beach, gather for a group meal, and enjoy a true “together but not cramped” experience.
20th Street Homes
Side-by-Side Beach Houses Perfect for Large Groups
Looking for multiple homes within steps of each other? Our 20th Street properties are ideal for families or groups of friends who want to stay close, but still enjoy their own space. These four beach houses sleep 6–10 guests each and are just a short walk to the oceanfront, making them perfect for wedding guests, family reunions, or sports teams needing proximity and comfort.
Guests love the full kitchens, laundry access, porches, and convenient parking. Staying together has never been easier—or more comfortable.
Bayberry House
A Spacious Retreat for Bigger Gatherings
If your group would rather all stay under one roof, Bayberry House is a standout option. This large, beautifully designed home offers generous space for bigger groups—ideal for family reunions, small retreats, or any celebration that calls for a little extra room to spread out.
As one of our top vacation rentals for large groups, this home sleeps 17 people, has spacious communal areas, a fully equipped kitchen, and outdoor space to relax. Bayberry provides a welcoming retreat just minutes from the beach and local attractions. It’s group travel, elevated.
Let’s Make Group Travel Easy
We know planning for a group comes with its own challenges—that’s why we’re here to help. Whether you’re booking multiple homes for a wedding weekend, organizing a family reunion, or coordinating for a tournament, we’re happy to help you find the right fit and even offer discount codes for group bookings. Email us cs@transcendentstays.com for details.
Ready to start planning your group stay? Browse our vacation rentals for large groups or reach out directly and we’ll help you piece it all together!
