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Ahead of the Curve: Vacation rental smarts

Finding your visitors spots that suit them most

Illustration by Adam McCauley


We’ve all been through the three stages of hosting houseguests. First, there’s the “honeymoon stage,” where you stay up late, catching up over a bottle of wine. Then there’s the, “Wait, you’re staying how long?” phase, which usually starts about the time you come home to find they’ve broken into that bottle you were saving for a special occasion. Finally, there’s the “Will they ever leave?” phase, which usually involves you, drinking wine alone, surrounded by piles of your guests’ dirty laundry.

Which is why, this year, we are all about vacation rentals. Hook your houseguests up with a sweet condo on the beach and neither of you will ever have anything to whine about again.

Book early: “The days of plentiful, cheap rentals are over,” says Lesley Garlock, owner of Southbay Realty. “If you see something you like, book it.” In fact, some of the better rentals are booking an entire year in advance. Garlock suggests you scope next year’s rental while you’re in town this year.

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Hit the park: Garlock recommends renters with furry family members check out the Naples Park neighborhood, which doesn’t have the same strict homeowner association rules that many condo complexes have. “Plus it’s close to the beach, the Mercato; it’s just a great area.”

Who ya gonna call?: Hopefully you won’t have to call anyone about roaming ghosts, but if the oven door falls off on Christmas morning, make sure you have a name and number to call.

Know what’s included: Anyone who has rented a beach condo only to arrive and find that “includes beach equipment” means one broken snorkel mask and a sand shovel knows that asking for an inventory list is key. Any well-organized rental property should have a complete, itemized list for beach equipment, kitchen gadgets and linens.

Pay to play: If you’re coming for golf, know that renting a property in a golf community doesn’t necessarily mean free rounds. “It’s property by property, but most places you’ll have to pay a guest fee for games,” says Scott Dougherty, the director of the rental division at Premier Sotheby’s International Realty.

Shop online, at your own risk: VRBO.com (that’s Vacation Rentals By Owner) and Craigslist can have good deals, but know that scams do happen. If something seems too good to be true, it probably is.

Seeing is believing: If you’re not close enough to check out a rental in person, send a friend. If that’s not an option, send the Realtor and videoconference as he or she walks through the home.


150,000: Minimal estimates for the number of seasonal residents who come to Southwest Florida in the winter


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