1. Always book from a reputable real estate rental agency
Although you may find better deals on web sites such as craigslist.org, you don't have the protection of an agency to fall back on if there is a problem, or if the listing is a scam. I've seen too many horror stories on the news to ever trust a landlord that I don't know who is booking their own listings. Wouldn't it suck to pull up to the "Beautiful Beach Bungalow" and find that you booked a "Shitty Sand Shack"?
2. Avoid properties that advertise "owner on site"
Although this seems like a positive feature, it can be an absolute nightmare (trust me - I speak from experience). No matter how well-behaved you and your family may be, it will never be good enough for the person who owns the unit. That person may be next door or downstairs and will be watching your every move and may even decide to "stop by" when you're out to dinner one night to "water the plants". Oh...hell....no.
3. You need central air
Really. You do. If a listing does not specifically state that the house/condo has central air, it may not have it. It may have window or wall units, or nothing at all. Be sure that you are clear on this before you sign a contract. Wall and window units are noisy and could block that beautiful ocean view!
4. Rental property owners are trying to make money - not spend it
When you show up for your vacation, you may notice that the property doesn't look quite like the photos that were on the web site you booked from. This is usually because the photos were taken many years ago - before the property suffered the wear and tear of 16 to 20 different families each summer for 5 years straight. You might want to ask your rental agent how recent the photos are before you book. Unless a property owner uses their rental for their own vacation, there's a very good chance that they may not be keeping the furnishings in good repair.
5. Pack your cleaning supplies
All rental properties are supposed to be clean when you arrive. I can honestly say that 75% of the rentals that I have walked in to have been dirty. Some times it was just that the cleaning crew had not arrived yet. But a lot of the times, it was because they arrived and didn't do a good job or, in the case of the last place I rented, the owner's sister used the unit last and was supposed to clean before she left. Either way - you're probably going to have to pee as soon as you arrive. Have your antiseptic wipes ready to go and you'll be ready to "go".
6. Be prepared to bring some amenities from home
Not every property will have things like irons/ironing boards, sand chairs, and ice buckets. If you have a creature comfort that you can't live without for a week, you'd better pack it.
7. Take the right size linens
Check the bed sizes before you pack your linens (sheets and towels are almost never included in a weekly rental). A few years ago, I had to search all of Ocean City for King-sized sheets after I checked in to a condo because I assumed that the master bedroom bed was a Queen. I always found it helpful to pack my sheets and towels folded in a laundry basket that I could use as a "hamper" during my stay.
8. Be respectful to your neighbors
As soon as I met my beach house neighbors, they asked me if I planned to rent my property out (usually with a distinct nose sneer). Renters get a bad rap - especially in condos or townhomes. Try not to piss off the neighbors by being too noisy, smoking on your balcony when they're out there having their morning coffee, or taking their parking spaces. Don't give them any reason to call the property owner, rental agency, or - god forbid - the police. Remember that you're on vacation, but your manners still need to show up for work!
9. Don't get caught in check-in day traffic
Most rental check-ins are late afternoon on Saturday. This means that everyone will be wanting to arrive shortly before that. This also means that everyone will be leaving home at the same time and will be on the highway at the same time. The only way to avoid the back-ups is to leave really early in the morning (before 8 AM) and find a place to hang out before you can pick up your key. Or, arrive late. If you're willing to show up at 5 PM (or shortly before the rental office closes), you will have avoided the entire mess and, hopefully, can breeze in to town, grab your key and have a relaxing evening.
10. Remember that it's only temporary
Try not to let little annoyances ruin your vacation. Every rental will have something about it that you don't like. If it's nothing major, try to let it go and enjoy the things you do like. By the time you get checked in, you really only have 6 short days left to relax and have fun. Don't ruin them for yourself or your family by focusing on anything negative.
There are only 166 days left until the first day of summer. Ready. Set. Rent!!