As the owner of Gertrude Rentals I’ve booked thousands of Siesta Key and Vermont vacation rentals and I love the job, but it has its headaches.  Florida has house-geckos hurricanes and noisy parakeet colonies, and Vermont has blizzards bear and red squirrels (terrible, worse than bear)!   Still the biggest challenge is filling the rental calendar.  Use the tips below next time you book and I guarantee you’ll save enough to pay for kayak rentals, horseback riding, a lobster and champagne dinner every night, or even a second vacation. 

Book Dates Last Minute to Save 50% Or More

Booking a vacation rental last minute might mean paying up to 60% less than the group next door paid for the same unit.  How is that possible?  When you book last minute, you’re filling dates that would pass by unoccupied and that means found money for the rental manager.  The more last minute the booking, the bigger the discount.  If I get a request for a checkin this week, I’ll start by offering 60% off any property available.  Honestly, try it now, I can be reached or call me 917-842-9081.  You might even pair this with a cheap flight or an in-the-bag weather forecast!

Use the approach below to win a big last minute discount.  A smart owner will welcome last minute bookings, no worries if the manager is unresponsive, just move on.

  1. Introduce yourself  and describe your wonderful group in need of a vacation. 
  2. Be upfront but avoid being pushy.  You may be thinking, “How do I ask for 50% off and not sound pushy?”, just explain you are “reluctant to ask for a discount, but love this unit and cant quite afford it”. 
  3. Finally make it easy to say “Yes” to by being easy to deal with and responsive.  Owners should be happy to answer questions, but right in the middle of a request for a 50% discount might not be the best time to raise esoteric concerns about amenities. 

NOTE – Last minute can mean booking two weeks prior to arrival for off-season and just 5 days prior to arrival for a holiday weekend.  When looking for in-season on the island of Siesta Key make sure you have a plan-B destination because it will fill up. 

Be Flexible With Your Travel Dates to Save 20% to 40%

While searching vacation rentals watch for scenarios where a small date adjustment might perfectly fill a gap in a rental managers calendar.  Whether it’s shortening or lengthening your stay, ask if flexible dates would help the manager get you a better rate.  If making a one to two day change eliminates a calendar gap and raises the managers occupancy rate, they might just give you a nice discount or even throw in a night for free to land the booking.  If the owner is using a pricing algorithm to set their rates, test the days of the week to see if Tuesday to Thursday is much cheaper than Monday to Wednesday.  

NOTE – Weekdays are usually cheaper than weekends and I “for one” frequently price my weekdays 50% below the weekend rate. 

Don’t think you can be this flexible?  Sure you can.  Most vacation destinations are in a cluster forming a hub and spoke meaning your principal destination will be surrounded by less highly coveted, but often attractive destinations.  My Vermont properties, for example, are in the heart of New Englands skiing eating and wellness country.  When I can’t accommodate a guest for a day or two I recommend staying a night at a B&B in an adorable nearby shire like Chester, Weston or Manchester Village.  For my Siesta Key properties the nearby attractions are endless.  Guests flying in or out of Tampa could spend the first or last day of the trip visiting Ybor City, Lowery Park Zoo or Busch Gardens.  For Ft. Meyers flights visit Naples, Pine Island or the Everglades.  Whatever the destination, be sure to play, eat, drink, and make merry so the layover becomes an event in itself. 

Let the Owner Design Your Itinerary and Save 30% to 50%

Give your preferred dates to your host and let them propose units that work for you.  If your host can use your flexibility to fill calendar gaps across multiple locations, it can mean a big discount or a free upgrade. This might involve taking a unit that isn’t your first choice or moving mid-week, but the savings will be worthwhile and its a great strategy for finding an otherwise unavailable stay in a sold out location.  At my Siesta Key properties switching units can mean just moving two doors down the balcony, or driving 3 miles from quiet Crescent Beach to one of the my more lively Siesta Key Village houses.  

NOTE – When switching units mid-stay you might experience a delay between the time you check out of one unit and check into the next.  At our Gertrude Rentals properties I can schedule the cleaners to avoid your becoming “momentarily homeless”, but most properties do have a 4 hour delay.  Ask your host what to expect and plan to use that time to take in a nice brunch or bike ride. 

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