Assess the stair situation.
If you're traveling with in-laws or infants, be sure to ask how many stairs are inside (and outside) the house. Taking a tumble isn't a great way to start—or abruptly end—your dream trip, so be sure to get all the details: Are there steps to the bedroom? Bathroom? Back deck? Are these areas well lit? If not, pack a night-light to ensure that sleepwalkers both small and tall don't go bump in the night.
Plan for a baby on board.
Is the house equipped with a crib, high chair, baby gate (see stairs, above!), and other baby essentials? Many times they are, and if you can avoid hauling a portable nursery, you'll free up space for souvenirs on the way home. As an alternative, ask the owners to refer you to a local rental service, or check out Traveling Baby or Baby's Away before you go.
Get the lay of the land (literally).
Expecting a flat lawn for football, Frisbee, or general frolicking? How big is the property? How close is the next house? Is the lawn level or sloping? Is there a stash of sports stuff available for your use? Is your dream rental a brisk walk away from the beach/lake/town/restaurants/parks/museums/etc.? If so, find out just how far that walk is. One person's "gentle stroll" is another's walk from hell, so be sure get clarity on proximity to local attractions.
Figure out the lowdown on where you'll scrub down.
Is an outdoor shower essential? Do you need a tub to bathe the tots? Would a glass door on that tub be a hassle? Are you used to a massaging showerhead, and nothing else will do? The devil's in the details here, so if what you're looking for is an oversized Jacuzzi but what they have is an old-fashioned soaking tub, it may be best to leave the bath salts at home.
Linens: to bring or not to bring? Know thy rental.
Many rentals, but not all, include sheets and bath towels but not beach towels. Some include beach towels but not the others. If you ask me, vacation means a break from washing sheets and towels and making beds. If you feel the same way, be sure to ask so that sweet dreams await when you arrive...rather than chores like making your bed and lugging a pile of dirty linens home. There's no quicker way to lose that vacation vibe!
Ask what fun stuff is included.
There's an excellent chance that a full supply of summer entertainment awaits in the basement or garage; many rentals come with the use of a beach umbrella, chairs, coolers, bicycles, and more. Also ask about books, blocks, and board games; discovering someone else's favorites can be a great part of the rental experience. In case you or your kids are hooked on Wi-Fi (who isn't these days?), be sure to ask if the house has it and what the code is.
Grab the garbage pickup schedule.
Who's responsible? What gets tossed versus recycled? Where should you put it? When is the weekly collection? Do you take it to the curb, or do they take it to the dump? Or, heaven forbid, are you expected to take it with you?! Smelly trash will certainly put a dent in your summer fun, so sort this out in advance, and you won't spend your downtime sorting cans and bottles.
Make sure your pets (or your pet allergies) will be accommodated.
Whether you can't stand to leave Fido behind or the mere thought of him makes you itchy, it behooves you to ask about pets. If you plan to bring your pooch (or other animal friend), ask where you can walk him, where to dispose of his "droppings," and if the local beaches, parks, restaurants, etc., are open to having him tag along. If allergies are your issue, ask if the owner has a pet or has allowed other renters to bring theirs. If the answer is yes, you may want to keep looking.
Investigate whether the house will be an oven or an icebox.
Some like it hot...and some don't. Depending on where you're headed, ask if the house has air conditioning and/or window fans. If a cabin in the mountains is more your thing, ask if there is a fireplace; if so, are you allowed to use it? And is firewood supplied? Are campfires allowed? Is there a grill? That's a flame you just may want regardless of the temperature...and be sure to ask if it's gas or charcoal so you can plan accordingly.
Read the fine print.
Before you get swept away by the majestic photos on the rental listing, look into the nitty-gritty: How much is the security deposit, and how quickly will it be returned if there is no damage? If there is damage, how will those fees be handled? Is there a minimum? Is there a cleaning fee? Asking these questions up front will eliminate any disappointment or surprises when you vacation is over.
If you like to start your day the caffeinated way, be sure to ask if the kitchen has a Keurig or classic drip brewer. That way you'll know whether to pack the K-Cups or the beans, and you'll be able to enjoy a warm cup of your preferred morning brew as you take in your vacation view.