Posted on 3/8/2021

How to Keep your Hilton Head Vacation Rental Fully Booked in 2021 and Beyond!

Being a vacation rental property owner is not for the faint of heart. Between property upkeep, managing reservations, meeting guests’ expectations, and making sure your investment is protected can be stressful and time consuming, even for the most seasoned real estate investor! But one thing that keeps every single vacation property owner up at night is rental occupancy. Ensuring that your Hilton Head vacation rental is fully booked year-round is imperative, and most importantly, absolutely possible. We share with you how in this blog post


With the sea of vacation homes available on Hilton Head Island, you need to ensure that your home is competitively priced. This does not mean slashing rates or running promotions that may cut into your profits. On the contrary, it means to offer your home at a price that is advantageous for both you and guests, based on seasonality, special events in the area, and available vacation rental inventory. This is one of the many reasons we have an algorithm-based pricing tool called Dynamic Pricing. This algorithm allows us to adjust prices in real time to ensure that our clients’ homes and their rates are both competitive and profitable; a win-win for guests and homeowners!


Nothing compels someone to book an island vacation more than prolonged snowstorms and inclement weather.

While the climate on Hilton Head Island is fairly pleasant year-round, not everybody across the country experiences the same enjoyable temperatures and beautiful scenery, especially in the cold months. This is why it’s important to have a strategy for messaging prospective guests in locations experiencing snowstorms, ice fronts, or other harsh winter conditions on a regular basis. For our homeowners, we have a robust social media and email marketing strategy, targeting prospective guests in the Midwest, Northeast and Mid-Atlantic, where snowstorms and ice fronts are fairly common for about five months of the year. By using messaging that speaks to prospective guests’ needs and desires to go somewhere warm, we meet them where they are, so they come to where your home is.


While seasonality influences the revenue performance of a vacation rental, on Hilton Head Island there is a season for everything and everyone. Snowbirds from the Midwest and Northeast take advantage of our month-long rentals in the winter, while golf enthusiasts come to see us throughout the spring, especially during RBC Heritage. The summer and early fall months are the perfect time for families to come and enjoy the beach, while November and December are the perfect months to book large vacation homes and host extended family gatherings for the holidays.

 For our homeowners, we do not scale back on marketing; we fine tune our messaging. Instead of focusing only on marketing properties during “high-booking season”, we use our knowledge and experience of the market needs and adjust our messaging strategy to appeal to different guest types. We use hyper-specific targeting parameters, from geolocation to interest-based targeting, and appeal to the broad range of Hilton Head visitors, with something that is of interest to them throughout the year. The length of stay for our robust marketing initiatives is always year-round. 

As you prepare your vacation rental for year-long bookings, keep these tips in mind and contact us to learn more about our homeowner program! From our unique local perspective and hyper-personal team of Vacation Experts to our razors-edge marketing efforts and income-enhancing policies, we create a curated island experience tailored specifically to your unique home. Contact us now at

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