​Vacation Rentals – How Far Out Should You Book?

Back​Vacation Rentals – How Far Out Should You Book?

By John Di Rienzo

At Exotic Estates, we focus on the luxury or high-end of the vacation rental market and our primary market is Hawaii. Hawaii is a year-round destination and is always in demand. However there are peak periods for travel to Hawaii, and other popular destinations, that impact how far in advance you should plan your vacation.

While this post will focus on Hawaii, it can be used a general rule of thumb when planning to rent a vacation rental in Hawaii, or another hi-profile, in demand destination, such as Park City during ski season or the Caribbean during the winter months.

The Holiday Season: 8 -12 Months Out

If you are looking to travel in December for Christmas and/or New Year, know that this is peak season for Hawaii and many other destinations. Children are off from school and business gets quite slow; some businesses, like ad agencies, often close. Lots of people look to spend the holidays away in a warm place, with family and friends. As such, the best homes are often booked up to a year in advance.

If you are serious about renting a home for Christmas and New Year’s, you should make the effort to look at availability a year to eight months out to ensure that you will have options. If you wait, you may get lucky and find a home that works for you, but you will have limited options.

The same applies to the Thanksgiving holiday period, though there is a lull between Thanksgiving and Christmas that represents an opportunity as pricing is reduced.

K-12 Seasonal School Holidays: 6 - 8 Months Out

Generally, schools in the U.S., which generates the majority of visitors to Hawaii, have breaks in the school year that are popular times for taking family vacations. Winter break takes place in February or March, while spring break will often take place in April around Easter.

These weeks can play havoc with your plans if you are planning on taking advantage of your kids’ school holiday for week away in paradise. Wherever you plan on going, if it’s a popular spot – beach or snow - expect competition and book well ahead.

Again, you might get lucky and find that perfect home for your family, but your choices will be more limited if you wait until four or three months prior to book.

K-12 Summer Break: 4 - 6 Months Out

People sometimes think that Hawaii must be more affordable and accessible in the summer because, well, it’s warm everywhere in the North Hemisphere then so what’s the motivation: wrong. Summer is a popular travel season in Hawaii and prices, and space, are at a premium. The reason – K-12 summer vacation, which can run from June to August.

Again it is the K-12 school year schedule that you must contend with during the summer months. Summer is family vacation time. Schools are closed, and it’s generally a period when business slows and folks take vacations from work.

However, in Hawaii you can find some great spots that you might not normally consider during the summer months. An example is the famous North Shore of Oahu. Gone are the giant waves of winter. The North Shore is placid and peaceful during the summer months, offering perfect, fairly empty beaches for family recreation. If you’ve been to Hawaii before and are looking for a quiet place for your family to relax, consider the North Shore, as the surfers and their groupies found there during the winter season are gone!

We do have some amazing destinations in our portfolio besides Hawaii that offer exceptional value during the summer months. One is Park City, Utah. There is actually lots to do in Park City during the summer and it can be a lovely spot for a family vacation. Also, pricing for our villas in the Caribbean will generally be lower during the summer months, as demand is lower.

Shoulder/Low Season: Fall Opportunity!

If you have the luxury of being able to take vacation during a low or shoulder period, meaning during the fall and not during the peak periods, you will typically find better pricing and better availability. So, if you are not tied to a school vacation schedule or better yet, are retired, you are in a great position to get your pick of vacation rentals.

Also, because demand is lower, you should be able to plan a trip in the fall closer in, say 3 – 4 months in advance, especially if you are flexible. This is true in Hawaii, the Caribbean and elsewhere.

A Note on Airfares

You can think about vacation rentals in a similar manner to airfares. In the airline world, there are a few seasons that can impact price: Peak (Holiday Season and summer), Shoulder (periods bordering peak), and Low (fall and periods not adjacent to common holiday weeks).

You can wait to see how fares move if you are traveling in the shoulder or low seasons before making a purchase. It is a worthwhile gamble. However, if you are traveling during one of the peak periods or your dates are not flexible, you should think about booking well in advance. Airlines keep pricing high during peak travel periods because they know they can and fares rise quickly as availability disappears.

Also, even during low season, if you must travel of specific dates, you can get caught in an availability crunch. Flights can get heavily booked on the particular dates you want or need to travel on, resulting in airfares that are unusually high for period.