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"Advice on renting a vacation home"
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Go to VRBO.com or Vacationrentals.com
Also, if anyone in your group was ever in the military, you can get cheap condos at http://www.afvclub.com These are leftover RCI timeshare resorts all over the world for around $50 a night.
Also, If nobody in your group was in the military, all you need is a relative or friend who was. They can purchase a gift certificate for you.
Be careful w/the VRBO & vacationrentals.com sites. Make sure that you are renting from the ACTUAL owner, and not an owner's agent. Also be sure that the owner lives in the proximal area. I rented a home in the Keys this winter from a man in Wisconsin who was the actual owner. Problem was, he lived too far away to help with the multiple issues we had with the rental. Also, if you are going to be in going into Fla. or the Caribbean, question owners about routine pest control. Be sure they are doing it on a regular basis or you made be dining with creatures the size of yourself!! I speak from personal experience. I've made all the mistakes!
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I am interested in renting a home for 8 people - 4 couples. The location is somewhat flexible... probably southern US, the Caribbean or Hawaii. Any ideas?