The Best Times to Book Vacation Rentals and Airfares

The Best Times to Book Vacation Rentals and Airfares


John Di Rienzo

August 6, 2015

Some time ago we published a general guide on the best times to reserve a vacation rental in Hawaii. The post concerns reserving your vacation early enough for various seasons to ensure that that you find a home that is good for your needs.

Yesterday, the travel search engine, Skycanner, revealed some interesting findings about the best times to purchase airfares. While not specific to Hawaii, we thought this would be a very helpful planning guideline when read in conjunction with our recommendations for reserving accommodation at a Hawaii vacation rental.

Clearly, these are just guidelines, as availability can vary wildly for specific dates. The more specific you need to be or if you are targeting a holiday week, the more valuable these guidelines become. However, even if you are just starting to look and trying to get a general sense of when to plan and book, it’s a great start as it gives you some specific time periods to target.

To be safe, it is a good idea to sign-up for fare alerts from your preferred airlines or online travel agent. In this way, you will be made aware of deals to your destination. As far as vacation rentals, especially larger or more luxurious rentals, you should develop a relationship with a reliable and proven vendor, like Exotic Estates, as true availability is often not made public in real time. Moreover, there are often specific requirements for vacation homes that may impact your desire or ability to rent the home.

Skyscanner’s Recommendation on Booking Airfares

According to Skyscanner, the period around August 10, is an ideal time to purchase all holiday air travel tickets – Thanksgiving, Christmas and New Year’s Eve. This is based on purchasing patterns for 2014.

The savings of booking around this time versus other periods looks like this for each holiday: Thanksgiving week tickets nearly 5.5% savings, Christmas-time flights nearly 19% savings, and New Year’s Eve air nearly 15% percent savings.

Some additional insights from Skyscanner:

  • Thanksgiving: historically, booking flights 10 weeks prior (Sept. 14 to Sept. 20) could result in up to 4% in savings. Last minute bookings up to two weeks prior (VERY RISKY!)  might result in 3.8% savings.
  • Christmas: historically, booking during weeks of Aug. 31 and Sept. 28 could generate 12.7% savings and 9.1% savings respectively. Last minute bookers in the first week of November saw savings on Christmas flights of nearly 4.8% saving. 
  • New Year’s: historically, booking during the week of Sept. 14 and the week of Sept. 28 can result in savings of up to 8.55% on flights. Booking New Year’s travel last minute, during the week of December 14th, could result in savings of 6.3%.

You can read more about Skyscanner on their website:

Exotic Estates’ Recommendation on Renting a Vacation Home

These vacation rental booking recommendations were written with Hawaii in mind, although they can be used a general rule of thumb when planning to rent a vacation home in any other in-demand destination, such as Park City during ski season or the Caribbean during the winter months.

The Holiday Season (Thanksgiving and Christmas & New Year’s): 8 -12 Months Out

If you are looking to travel in November for Thanksgiving week, or in December for Christmas and/or New Year, know that this is peak season for Hawaii and many other destinations. 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.

TIP: opportunity - Thanksgiving to Christmas Lull

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 generate the majority of visitors to Hawaii, have breaks during 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 thinking of taking advantage of your kids’ school holiday to spend a week 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 booking.

K-12 Summer Break: 4 - 6 Months Out

People sometimes think that Hawaii must be more affordable and accessible in the summer because: wrong. Summer is a popular travel season in Hawaii and prices, and space, are at a premium. The reason is K-12 summer vacation, which can run from June to August.

Check out our Hawaii vacation rentals today!


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