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10 Steps to Get the Best Deal on an Island Vacation Rental

October 6, 2015

1. Choose an island that is close to the mainland to decrease transportation costs. Flights are expensive, so if you can drive over a bridge or take a ferry to get to your island getaway even better. This first step will save you big time both on flights and on unnecessary car rentals.

2. Schedule your vacation during the off season. You will be amazed at the deals that you can get simply by traveling when the school year has started. For example, temperatures in late August all the way to November are still tropical in Florida and along the Southern Gulf Coast. The best months to travel during off season are May, September, October, November and the beginning of December.

3. Be open to last minute deals, and be flexible with your dates. If you can do this, you will be amazed at the low prices you can book. Often at half the regular price!


4. Sign up for newsletters with your favorite vacation rental or agency. You’ll get insider information on last minute deals available, often with extra incentives just for being a loyal follower.

5. Book a vacation rental versus a hotel/resort. When you are traveling, it is more economical to rent a home versus the price of a resort or hotel. You also garner savings by dining at home and it’s a plus when you don’t have to share the pool with others.

6. Become a return guest. Don’t be shy to ask for a discount when you are a model guest. Vacation rental home owners love return guests who respect and take care of their home and will often agree to a discount if you fall into this category.


7. Book a longer stay to gain a larger discount. As a traveller you have more leverage when you stay longer, because the homeowner/property manager doesn’t have to “manage you” as you become familiar with the home and there is less administration work for them.

8. Once you book your vacation, research the local scene and start subscribing to local vendor and restaurant newsletters. It’s not just the vacation rentals, hotels and resorts that need your business during the off season. Discounts can be found everywhere.

9. Book outings that are in group settings, it’s cheaper than chartering your own. For example; kayak and boating tours are a fraction of the price for a group rate.


10. Take advantage of the Fall Season 2015 by booking an October stay at Sea Life Happy or Surf’s Up in sunny Anna Maria Island, Florida. Currently offering slashed rates and a $450 gift certificate redeemable at Beach Bums Island Attitude for stays at their vacation rentals, during October 2015. Terms and Conditions apply. Contact Scott & Joda Coolidge for small and larger parties at [email protected] Or check out their listings at and


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