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Virginia Beach Winter Rentals Guide

Virginia Beach is known for its miles of beaches, a vibrant boardwalk, ocean activities, and a beautiful summer vacation destination. However, what many people don’t realize is that it’s also a fantastic and eventful coastal city even during the winter months.

Cooler weather? Check.

Empty beaches for peaceful walks? Double check.

Oceanfront living at a fraction of the cost? Triple check!

The combination of all these factors are just a few things that make a Virginia Beach winter rental so magical.

Is a Virginia Beach winter rental the right match for me?

Many rental property owners and management companies convert their short-term fully furnished rentals into long-term rentals during the winter off season. They often offer special discounts and promotions during the winter months, so their properties don’t sit empty.

These long-term fully furnished rentals often range from one to nine-month leases typically from September through May. The best part for those searching for winter rentals in Virginia Beach is that there is no shortage of options, ensuring you can find a place you’ll love whether it’s oceanfront, close to the ViBe district, near your coffee shop, or an abundance of other options!

Couple beach

A Virginia Beach winter rental is perfect for:

  1. Traveling nurses
  2. Remote workers
  3. Military personnel
  4. Anyone wanting to visit before moving
  5. Someone needing a place to stay during a home remodel
  6. Travelers on a budget
  7. “Snowbirds”
  8. Families seeking a budget-friendly beach vacation
  9. Couples who want a romantic, peaceful getaway
  10. Nature lovers
  11. Individuals wanting a peaceful, relaxed stay

Popular areas in Virginia Beach for winter rentals

The city hosts a multitude of different beaches and districts each with unique experiences to offer and makes for great places to stay. 

Here are some of the popular areas to consider:

  • Oceanfront: The Oceanfront area features rentals all within walking distance of the beach. In the winter, it transforms into a peaceful and serene location with stunning ocean views. This area is ideal for those looking to rent a place close to a variety of different restaurants, the boardwalk, live music, shops, and more.
  • Chesapeake Bay: On the north side of Virginia Beach, you’ll find the Chesapeake Bay area. It’s a charming spot known for its calm waters and beautiful sunsets and is perfect if you’re looking for a more laid-back place to stay.
  • North End: The North End is a quieter and more residential neighborhood in Virginia Beach, just below Chesapeake Bay. A huge draw to the area is 1st Landing State Park, one of Virginia’s most visited state parks featuring a multitude of hiking and biking trails, water activities, fishing and boating opportunities, and more. This area is perfect for the nature-lovers and those who prefer a peaceful winter retreat close to the beach.
  • The ViBe District: In the heart of Virginia Beach is the ViBe District, located from 16th to 22nd Street and just a short walk to the beach. This area is known for its creativity, culture, and community and is a perfect haven for artists, entrepreneurs, and residents who share a passion for the arts and a desire for an immersive urban lifestyle while still enjoying the oceanfront.
  • Old Beach: Stretching from 22nd to 30th Street, Old Beach is one of the first residential areas to be established in Virginia Beach. It’s characterized by cottage-style homes, tree-lined streets, and a thriving local arts scene and community. Residents can enjoy the ability to bike the whole community and live within walking distance of the beach and boardwalk.
  • Southend: Nestled between the Rudee Inlet and the Atlantic Ocean is the Southend of Virginia Beach, characterized by its laid-back coastal lifestyle. This area is especially known to be a great spot to surf, kayak and paddleboard but also hosts of plethora of different experiences like local restaurants, the Virginia Aquarium and Marine Science Center, parks, and more.

When picking your winter rental stay in Virginia Beach, it all depends on what you want to prioritize: proximity to the beach, level of activity, and type of accommodation are a few things to consider during your winter rental search. Whether you want a cozy beachfront home or a modern condo with city amenities, you’ll likely find a suitable rental property in one of these areas to make your winter stay in Virginia Beach more than enjoyable.


Tips for first time long-term winter renters

1. List your must-haves:

Do you desire windows overlooking the ocean? Or a place that is pet-friendly? Maybe you want 4 bedrooms? Or a backyard with a hot tub? Be sure to list your absolute requirements as well as flexible requirements which will help you find your perfect rental at the right cost.

2. Research the location:

As mentioned earlier, Virginia Beach has a variety of different districts each with completely different experiences. Do you want to be near the beach? Want more of an urban feel? Close to your favorite nightlife? Make sure you do the research beforehand to choose a rental in the area that supports the lifestyle you desire.

3. Plan ahead!:

Do not procrastinate looking into the winter rentals market. Although there are many winter rental options, there aren’t as many as the summer season and great homes with the best pricing go quickly so plan ahead. Winter rental owners tend to start marketing their properties in the early summer months.

4. Think about lease-lengths:

Winter rentals in Virginia Beach typically range from one to nine months starting in September and ending in May. However, many property owners are willing to be flexible with their leases because they don’t want their properties sitting idle. If a lease length is too long for you, don’t be afraid to propose a shorter lease, however, the monthly rate is likely to increase with shorter leases.

5. Market yourself as a great tenant:

Renting in the winter is the perfect time to sell yourself as the perfect tenant. Show up early to meetings and showings, be kind, and create a solid foundation for a relationship with your landlord which will make things much easier in the future. To speed up the process of securing your winter rental, be ready with a form of identification, proof of income, a payment method, your rental application, and always be honest about your credit, rental, and criminal history.

6. Communicate with the landlord:

Beforehand and as you begin renting, ensure you have clear communication with your landlord. Don’t be afraid to ask them questions a

Where should I start looking?

Winter renting is an investment, and it’s wise to do as much research as possible beforehand. Thankfully, there are many great options in the area to fit the lifestyle and experience you desire.

Here is a list of a few winter rentals that Transcendent Stays offers in a range of different locations and price points:

Kitchen chairs

A winter rental in Virginia Beach is a great option for those looking for a beautiful coastal city to experience but don’t want to pay in-season summer prices. The off-season offers a unique opportunity to make beach-living a dream come true.

Be sure to make the most of your stay in Virginia Beach’s winter by experiencing all the city has to offer and staying in a top-of-the-line winter rental. From the Chesapeake Bay to the South End, Transcendent Stays has a winter rental you’ll love.

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