Vacation Home Rentals Blog

I saw a funny Facebook status update today: “SeaWorld yesterday, Animal Kingdom today, breakfast with Chef Mickey and a whole lot more tomorrow! The kids (both big and small…) are having a blast!”

It struck me as odd that this family was taking its vacation at the end of September, but it makes perfect sense come to think about it. The girls aren’t in school yet.

No crowds, manageable temperatures of 80s during the day and 60s at night.

Why aren’t more families doing this?

Well, if your kids are 5 and up, obviously the opportunity won’t come around until spring break, but the under 5s will indeed have a blast with Mickey and friends. Plan a trip to an Orlando vacation home during the work week, and here’s betting you have the run of the rides and avoid even the locals. If you time it right, you may even hit multiple theme parks–Universal, MGM, Animal Kingdom, EPCOT, SeaWorld, etc.–and the outlets.

Look at you, multitasking while on vacation. Who said you weren’t a supermom?

You’ve heard the expression, “When everyone else abandons you, at the end of the day, at least you have your family?”

The saying comes to mind after seeing a story in The Ledger, a newspaper in Lakeland, Fla., about how Floridians are taking more trips in state despite an overall decline in visits by international and out-of-state travelers. To survive this temporary slowdown, Florida vacation home owners will need to market to their own.

Jackie Ewing, a member of the Central Florida Vacation Rental Managers Association, cited a U.S. Department of Commerce statistic that Florida suffered a 4 percent dip in travel this year, reportedly the first since 2001. She encourages short-term rental owners not to overreact by slashing prices, but focus on creating valuable, well-timed packages and email blasts and using Twitter–a free marketing tool–to entice tourists.

Florida landlords: What tactic has worked for you? Do share.

So it isn’t exactly family vacation season, but you’re a parent, you think months, even a year, in advance. When three school schedules are involved–not to mention the money it will take to squirrel away for bathing suits, amusement park admission and random stuffed animals–you’re smart to plan now.

The question is: Where should you go?

Whether it’s winter or spring break, here’s our handy guide to the best family vacation spots in the U.S. (in no particular order)

1. San Diego vacation rentals
San Diego is the proud home to a zoo that consistently receives high marks for its educational exhibits, including the world-famous pandas, and Balboa Park, the largest urban park in the U.S. with a collection of 15 museums. With gratis IMAX movies and all the trains, cars, planes and dinosaurs to keep little ones occupied, the words “I’m bored,” won’t be a concern during this vacation.

2. Orlando vacation homes
America’s families have been visiting Mickey Mouse and Shamu for decades, but come spring 2010, a new kid will cast a spell on Orlando: The Wizarding World of Harry Potter at Universal Orlando Resort. The theme park cares about details, enlisting the help of the films’ production designer and art director to spin the fantasy of “reel life,” from Hogwart’s castle to Dragon Challenge, a pair of roller coasters that mimic the effects of the Triwizard Tournament.

3. Chicago vacation rentals
The former city of the First Family may add Olympics summer headquarters to its resume (The official announcement is expected this Friday, Oct. 2), but you’d be crazy not to plan your first visit before 2016. The Windy City stands tall with its picturesque skyline, global palette, landscaped streets (surprisingly tidy for a big city) and family-friendly attractions like the Lincoln Park Zoo, Navy Pier and Millennium Park. Before you leave, don’t miss out on the 96th floor view from the Signature Lounge in the John Hancock Building, the Bean (or its technical name, Cloud Gate) and awesome digital faces on Crown Fountain. Your kids will most certainly geek out.

4. Destin vacation condos
Florida’s Emerald Coast is rich in vacation condos–many of them brand new–and some of the most breathtaking sand you’ll ever sink your pedicured feet into. The tykes will spend hours in the lagoon-style pools, splash pads and waterfalls. When it’s time to crash, they’ll retire to their bunk or trundle beds while you chill out on the balcony with a glass of wine. When mom and dad are happy, everyone’s happy.

5. Yellowstone Country vacation rentals
Maybe it’s been awhile since you were struck with childlike wonderment. The country’s first national park will make you feel like a cowboy, bringing tourists up close with its rugged terrain and geysers.  Register your 5- to 12-year olds in the Junior Ranger program, an interactive trip that rewards explorers by schooling them on principles of ecology, geology and wildlife. And while you’re at it, don’t forget to stop and watch the buffalo roam and the deer and antelope play.

Is a Facebook friend’s association enough to convince you to rent a vacation home?

A company in Oregon hopes so. Second Porch launched a new application on the popular social networking sight that connects potential renters with properties. Whether it’s an Oregon coast rental or Florida vacation home, travelers will be able to “friendsource” those listings they like, make recommendations and weigh in on the rentals, some 300 since the site completed initial tests this summer, according to The New York Times.

Some folks, however, prefer Facebook without a side of solicitation. People visit to see their cubicle mate’s antics from the bachelor party last weekend or the ever-pressing, important news that Jane Smith is about to get her teeth cleaned. When businesses start creeping in, does it become annoying, and would you download this application?

Another issue to consider: What if this friend’s listing doesn’t measure up to your expectation? Often friendships go sour with a bad business deal.

VacationHomeRentals.com takes the legwork out of your vacation home search, showcasing thousands of cottages, chalets, mansions, condos and apartments all in one place. You’ll stumble across user reviews, amenities, even the closest airport in a clean, straightforward profile page.

And any Facebook user knows that you can attach a link to any status update if you’re really trying to push something.

Let us know what you think on Twitter @checkincheckout.

New England and fall go together like a fuzzy sweater and a cup of warm apple cider. And for this picturesque season rich in auburn, golds and browns, wouldn’t it a blast to pack up the SUV for a long weekend in a Maine vacation rental?

Bing Travel named the state as one of its 14 Best Destinations for Fall 2009, and it’s easy to see why. The forests are thick, the towns are as quaint as an Irish accent, what with their antique shops, lakes and wood cabins. And along with its insanely affordable vacation homes, Maine is so serious about its autumn tourism that it tracks color changes on a website called MaineFoliage.com.

Most of the state is in “low mode” right now, meaning that the leaves haven’t hit their gorgeous peak yet.

But don’t wait forever. Before you know it, it’ll be time to pick out a Christmas tree.

If the American dream is a two-story Georgian with a white-picket fence, then the Hawaiian dream is a beachside bungalow with a thatched roof.

Don Ho and Hollywood did a damn good job of selling the Polynesian paradise–who wouldn’t want to be greeted by a pretty girl with a lei and a mai tai? But visions of tiki bars and flowery shirts make us forget that wait, people actually live there. Full time.

In Honolulu, the city council will consider this week whether to allow new b&b licenses to be issued following a 20-year freeze, according to the Honolulu Advertiser. It seems that lots of Hawaii vacation rental owners were listing their properties illegally, and the residents were not happy about it.  As many as 1,900 homes were operating without permits, the newspaper reported.

In a state whose financial health depends on a steady stream of tourists, the practice isn’t a surprise, but something’s got to give for the local taxpayers who argue that their communities are being disrupted by noisy transients.

And now you have the podium. Honolulu landlords, how do you feel about the issue? Locals, what’s a resolution that everyone can live with, while still allowing for revenue to be pumped into the Hawaiian economy? Talk to me on Twitter @ checkincheckout.

When someone else is paying, do you go for the steak dinner or the salad?

The latter? Me, too, but the greedy part of me wants the rib-eye, the appetizer and the Baked Alaska.

However, in this age of cutting pork, a very lucky crop of executives still get to travel on business,  have their meal and entertainment expenses reimbursed and stay in temporary housing. Those fortunate few may even have the luxury of working remotely or hosting company off-sites in fancy gated communities where outdoor kitchens, pools with grottoes and mountain views are standard ways of team building.

With the real estate fallout and the state in dire need of economic stimulation, California vacatation rentals pose excellent opportunities for corporate America to house their leaders, whether for long-term projects or short-term situations while candidates get settled in their communities.

Per the owner’s description of the Pasadena vacation rental above, “See the coast and Catalina Island on a clear day, downtown Pasadena views and purple mountain majesty every evening.”

That hardly sounds like work at all.

A Dallas woman got creative while hunting for a New York vacation home. She bought a $25,501 lighthouse at auction instead, according to The Dallas Morning News.

Pretty friggin’ cool.

So what if the six-story home sits on a cement block off the shore of Lake Ontario and lacks a little thing called electricity. But once the renovations are all complete, that’s a story that won’t be topped at the dinner party: I own a lighthouse.

For the rest of us non-creative consumers who don’t have the first clue about restoring historically significant architecture in the middle of a body of water, renting a vacation home near a lighthouse (like the North Carolina vacation home above near Currituck Lighthouse) is the more reasonable alternative.  These stacked homes are built for families, but having been there as a single, I can say that the communities of Corolla, Duck and Nags Head bode well for solo or couple weekends, too. What’s more romantic than strolling along the beach with a lighthouse in the background?

I’ll tell you what: knowing that your temporary space has a heated saltwater pool and hot tub waiting for you when you come back from your walk.

Oh, and finding security in the fact that if the weekend somehow goes bad, you won’t have to swim back to shore to escape.

No offense, Miss Nolan.

Some of us are still in the iffy weather period, with summer lingering just a little bit longer with gorgeous 70-degree temps. For kids, it’s a cruel joke, Mother Nature’s way of taunting, “Haha, you have to be in school.”

But the rugrats don’t have to miss out if you can squeeze in a weekend trip; it’s a lovely time to plan a fall getaway to a Virginia vacation home.

Take Interstate 64 to Colonial Williamsburg, where the falling leaves lend to a timeless backdrop for 18th century America. The men don patriot hats and wigs, while the women wear petticoats, and the buildings transport visitors to the American Revolution era right down to the Governor’s Palace. You’ll hear how African-American slaves endured plantation life and gain a new appreciation of tradesmen and women and their tools, from the blacksmith’s iron to the weaver’s spool.

Nowadays, it’s a misguided notion that working with one’s hands is the job of “menial” laborers, but these were clever, skilled artisans who sweat over dirt and fire to create the cotton that would be turned into quilts, the wax that would become candlesticks and the metal that would be fashioned into tomahawks.

If there’s shame in learning a skill for survival, you wouldn’t know that from visiting here.

For $8.75 million, you can bid on the home that Ponzi built: Bernie Madoff’s former private beach residence on Long Island.

The David Webb-designed house is surprisingly unflashy–fitted with Formica counters and on the smaller side compared with other properties, according to Fortune–considering its ex-owner pirated $65 billion from the people who entrusted him with their life savings and retirements.

Yet the new owner may feel a sense of giving back while enjoying those heavenly ocean views. All the proceeds from the auction and sale will go toward a fund for Madoff’s victims.

The rest of us, meanwhile, will be saving up for our next summer vacation at a Montauk vacation rental like the one above, a relative bargain at $1,500 a week to $3,800 a week depending on the month. The owner gushes about the area’s secluded dunes and virtually uninhabited coastline.

No wonder Bernie felt at home there. It was a hiding place.