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  • Scott Westfall

Renting A Winter Rental in Virginia Beach

Updated: Jun 12

Virginia Beach fully-furnished winter rentals.

Looking for a winter rental home in Virginia Beach? Hoping to find your next fully furnished investment property? Read on to learn more about winter rentals in Hampton Roads.

Living in an oceanfront property - like those found in Virginia Beach - is a luxurious yet attainable dream. Renting a long-term fully furnished rental during the winter months is a unique opportunity to get that beach-house life at a fraction of the cost that peak season demands.

Unlike some coastal towns, a long-term furnished stay in Hampton Roads (which comprises Virginia Beach, Norfolk, and surrounding cities) is a popular option at any time of year. The area is not only coveted for its beaches but its vibrant community and access to nature. Renters looking for exceptional community and mild weather during the winter don’t need to look any further than winter rental hot spots in southeastern Virginia.

Are you an owner of a Virginia Beach vacation property looking for tips on converting your short-term rental into a winter rental? Check out this guide for Winter Rental Owners.

Is a winter rental in Virginia Beach what I’m looking for?

Instead of letting their fully furnished vacation rentals sit vacant during the off-season winter months, hundreds of investors and rental property owners in Virginia Beach and neighboring cities convert their short-term rentals into long-term winter rentals each year. As a leading region in military and industry, the area always has a market for rental properties.

Hampton Roads sees new families move in all year round. Many of these newcomers to the area prefer three- to eight-month leases in furnished homes to get to know Virginia Beach and its surrounding cities better before buying a home or settling into a more substantial lease. Some need a bit more time to decide between buying or renting long-term.

Virginia Beach could be the perfect winter rental location if you are:

Where can I find winter rentals in Hampton Roads?

As a beach town, Virginia Beach boasts many fully-furnished homes right near the ocean used as short-term rentals during peak vacation season. When things slow down and Labor Day arrives, many of these beautiful homes are converted to suit the longer-term needs of winter tenants.

Neighborhoods with some incredible winter rental properties are:

  • Sandbridge: A smaller community located 30 minutes south of Virginia Beach’s main boardwalk area is Sandbridge. Known for miles of wide-open beaches, Sandbridge features the Back Bay National Wildlife Refuge and False Cape State Park. Quiet dunes and lots of space make it a perfect choice for single- or multi-family stays, as the area offers everything from massive 8-bedroom beach houses to modest cottages and condos.

  • Croatan: Croatan is a well-known community just south of Rudee Inlet. This neighborhood is known for its private beach and a warm and welcoming neighborhood feel. Croatan features mostly large single-family homes with stunning ocean views.

  • Old Beach & Shadowlawn: Old Beach & Shadowlawn are home to the creative arts ViBe District, the new Sportsplex, and Virginia Beach’s convention center. Most winter rental homes in this area are within walking distance to the boardwalk and beach. This lively community provides lots of things to do within walking distance from your rental property.

  • North End: Homes in the North End district of Virginia Beach come in all different shapes and sizes. Typically considered to comprise 42nd Street to 89th Street on Atlantic Avenue, North End also boasts the beautiful First Landing State Park nestled on 65th Street. Compared to Old Beach and Shadowlawn - which are geared towards tourism - the North End has a much more local feel. All North End properties are within walking distance of the beach.

  • Shore Drive/Chic’s Beach: Chic’s Beach - also called Chesapeake Beach - is a popular destination beach that is looped by the iconic Shore Drive. Vacationers have pilgrimaged to Chic’s Beach for more than 100 years to enjoy its 2-mile coast from the Lynnhaven Inlet to the Chesapeake Bay Bridge-Tunnel. Pet-lovers, swimmers, and paddleboarders enjoy the calm ocean located here.

Tips for First-Time Winter Renters

First time looking for a long-term, fully furnished rental? We’ve got you covered with these expert tips:

  • List your must-haves. Before researching rental properties, make a list of your ideals and needs, such as pet-friendliness, amenities like fireplaces or a high-end kitchen, and how utilities are covered.

  • Research the perfect location. Re-read the above section of this blog and Google the ones that look most appealing to you for a deeper dive. Also, check out this local activities list so you know which things to do you want to have easy access to!

  • Keep length of lease in mind. A typical winter rental property is leased for one to nine months at a time. In Virginia Beach, the off-season typically runs from September through May. Outside that, winter rentals generally have a higher weekly price.

  • That said…. Everything in real estate is negotiable - including winter rentals. In contrast to a standard yearly lease, winter rental owners are often more willing to negotiate lease lengths. For example, they might rent an 8-month property for three months at an increased rate, or if the renter covers utilities. So take a chance and start a conversation about that property that caught your eye.

  • Don’t procrastinate! Winter rentals can go fast. The inventory of fully furnished properties available for long-term winter leases in Virginia Beach is exceptional but limited. Local property management companies begin marketing winter rentals during the summer months.

  • Sell yourself as the perfect tenant. Winter rentals don’t have the market frenzy that short-term rentals in Virginia Beach do during peak season, so you have a chance to shine when you seek a lease. Arrive at showings on time and communicate clearly and kindly. Be honest about your credit, rental, and criminal history. Having your pay stubs and employment verification on hand can speed up the process of locking in that great home.

Where should I start?

Renting a winter rental property is an investment - it will be your home for a significant time, so getting expert help is something you’ll never regret. Talk to a real estate consultant who knows the area up and down to identify the right property for you and the best company or owner to provide for your winter needs.

While you can always check out the big sites for a full search, we have some local favorites that we recommend to our clients. Check them out:

The best thing you can do to make sure you’ve invested in a perfect winter getaway is to work with a real estate consultant to make sure all your considerations and options are covered. We want you to love Virginia Beach as much as we do.


Winter rentals in Virginia Beach are a dream come true for any beach-loving renter. The opportunity to live in an oceanfront house is a once-in-a-lifetime experience for many people.

Make sure to make the most of your winter by getting the perfect winter rental in the ideal Hampton Roads neighborhood. Our team of real estate consultants is ready to hear what you need and match you to your winter dream home.

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