Vacation Home Rentals Blog

We’ve all had Martha Stewart envy.

A Hamptons vacation home landscaped with a garden of organic produce, fresh herbs to pepper our from-scratch meals with and a backyard big enough to host an elegant, yet intimate wedding reception. Heck, you’ve paid a mint for the same New York vacation rental for years–why not get in on the game now?

Mortgage rates are at all-time lows. Prices are plummeting. If you wait for them to sink further, will you be missing out on the pastoral paradise?

Perhaps.

Second-home ownership–or any home ownership–is not to be taken lightly. Heed the advice of a realtor who knows the market, and determine what style of vacation home suits your lifestyle, whether it’s a condo, cottage or mansion. Take factors like location, amenities and upkeep into account.  Think about hidden costs. Can you afford to maintain the property yourself or hire a management company to deal with tenant issues?

While that $8,000 first-time homebuyer tax credit doesn’t apply to purchasers who won’t be using the property as their primary residence, by all accounts, now is a good time to strike the MLS.

Landlords: Any more advice for consumers who seek to purchase a vacation home?

This year, it’s pretty much a given that Black Friday and Cyber Monday shoppers will be able to score incredible sales on electronics, clothing and toys. The folks who wake up at 3 a.m. to stand in line at Best Buy are an aggressive bunch, and during this downturn, retailers are more than willing to dangle the deals.

Some of us, though, are happy enough with turkey and kickin’ back with our family. But what if you’re single and don’t necessarily want to go home this year? (Sorry moms, but as much as we’d love your homemade apple tart, we can’t return for every holiday.) Here’s a solution: Round up three solo friends and rent a Tennessee vacation rental.

The property above will be discounted from Nov. 25 to 29 to $585, the price of three nights for four. At almost 1,000 square feet, the Sewanee vacation home is still bigger than lots of city apartments if space prevents you singletons from gathering. Plus, how many places have a strawberry patch, private ponds and canoe on-site?

Of course, there’s the issue of whom cooks what, but that’s the fun of a community kitchen. You all get to taste (and test) together, and the pressure is at a minimum.

So what if you’re a Thanksgiving orphan. Think of it this way: If the stuffing is too soggy, your friends probably wouldn’t take as much offense as Aunt Cindy.

It’s almost time to start making your list and checking it twice, and maybe start nixing the frivolous purchases of the past. (Does every relative require a Hallmark limited edition ormanent? Come on now.)

Besides, experience gifts are all the rage. Haven’t you heard? Presents that will have the recipient asking, “Why did I never do this before?” Like smelling a Colorado Aspen for the first time, and maybe even cutting down his first Christmas tree.

Or heck, why not skip the iPod stocking stuffers and go on vacation together? Let me count the reasons for spending the yule in a Colorado cabin rental.

1. Because cabins mean fireplaces, roasting marshmallows, wearing obnoxious snowmen and reindeer sweaters, and perhaps catching a glimpse of reindeer in real life.

2. Because you’ll likely be skiing, too. You’ll need to after the green bean casserole, sage sausage stuffing and fudge log cakes.

3. Because if you’re going to be stuck with your relatives–all 20 of them–it may as well be in an eight-bedroom house complete with a pool table, hot tub, bar and multiple flatscreens. Just think of all the joy you’ll have when battling over who gets the last Wii control.

4. Because it will most likely be a White Christmas. (Stranger things have happened, but I’d wager my third born that there will be snow somewhere in Colorado in December.)

5. Does a Christmas tree get any more beautiful when lit inside a log cabin?

Poor Nevada.

According to RealtyTrac’s latest foreclosure report, one in 23 households received a foreclosure filing, making it the highest state for mortgage defaults in the U.S. About 13 percent of the population are unemployed. It’s the kind of news that makes you wonder if in desperation, folks went to Las Vegas casinos in a last-ditch effort to win this month’s payment at the tables.

Lady Luck, you’re a glitzy gal in that feather headdress and sequin costume, but underneath, you can be awfully cruel.

Just curious: What kind of traffic have you Las Vegas vacation home owners had in the rental market? While residents are fleeing Sin City, surely tourists are still coming, right? You tell me @checkincheckout.

It’s the second time Key West appears on the blogosphere this week, but with good reason.

Fantasy Fest, South Florida’s answer to Mardi Gras, parades into town from Oct. 23 to Nov. 1–feather boas, queens, chaps, conchs and all. If you tried the hotel route and failed, it’s time to snag a Key West condo rental now if you still can. The kinky time seduces regulars from around the U.S. who come ready to show off their creative displays of body paint and a momentary flash of, um, courage for plastic beads. The hundreds of thousands of spectators and participants swell the tourist destination to a veritable island of hedonism.

Duval Street transforms into a dance party with floats, wigs, live music, drag shows and cat calls. If you’re the shy type, play voyeur. If you’re the exhibitionist, channel that naughty nurse. Just don’t say we didn’t warn you if it ends up on YouTube.

If you can’t squeeze the fest in this year, there’s always San Francisco, the capital of kink. Mardi Gras too vanilla for you? Head to the International Bear Rendezvous in February to watch dudes scout dudes who don’t mind a little hair around their chests and girth around their bellies. The celebration raises money for local and national HIV charities.  And for more leather daddies, hit the Folsom Street Fair in September.

It’ll be a hoot.

This has to be a joke.

The Poconos house rental above lists for $1 million. That’s rent, people.

In the same posting, the owners of Lustgarten-On-The-Lake talk about how you can stay in their spacious Poconos Pine property for “peanuts,” which could mean just that. Will the landlords of this gem hit me on Twitter @checkincheckout? I’m impressed with your marketing tactic.

Because in a sea of listings, you still have to make your vacation home stand out.

Whether it’s a deck with sunset views, an outdoor kitchen next to a grotto pool or a location within the hottest neighborhood in San Francisco, you have to showcase your vacation rental just as aggressively as if it was listed for sale. Internet users are a savvy bunch who are willing to spend countless hours of “research” on the Web.

The Poconos house has a lot going for it already: a backyard lake with fishing rock, hot tub, fireplace, community pools and access to three ski areas nearby.

Would you pay $1 million for it? And if not, what would you pay?

Talk to me on Twitter.

Six winters in Chicago has definitely thickened my skin, but that doesn’t mean the sudden deep in temperatures doesn’t feel cruel and uncomfortable every time. Three weeks ago, I was wearing a denim mini-skirt. This week, I’m busting out the winter coat–and gloves.

A friend of mine, a victim of the recession who moved up from Florida, plans to head back home next weekend. No work in three months. Part of me felt sorry for her, the other thought, You lucky girl. Back to purple pink skies and 90-degrees and sunshine every day. How could that be so bad?

Collectively my city is moaning (and bracing itself) for what’s to come. A few of us, dreading that first attempt to shovel our cars from the snow, have pre-booked vacations to warmer climates starting in January to Virgin Islands vacation homes and Florida vacation rentals. The deals are out there, from last-minute deals to Tampa Bay to contemporary condos in South Beach.

Because regardless of where we live: We all know that sunkissed skin is like being on the receiving end of a warm hug from a long lost friend.

Friday is the grand reveal for the host city of the 2016 Summer Olympics, and to call it early, I’m going to say Chicago.

Disclaimer: The author of Check-In, Check-Out is a full-time, almost decade-long resident of the Windy City, and damn proud of it.

Why wouldn’t I want to show off my adopted hometown?

While the games are years off, it’s a sure bet that Chicago vacation rentals will play a big part of housing. In fact, I predict a rush on Chicago vacation condos suddenly populating this site and others, thanks to folks seeking their piece of the rings. Travelers shouldn’t be discouraged if they don’t land a room downtown–our neighborhoods along the glorious Lake Michigan coastline are our best-kept secrets, brimming with any kind of ethnic food you could ever want, legendary sports teams and funky shops.

Wrigleyville. Edgewater. Hyde Park.

Ever heard of it? It’s a certain president’s former zip code.

And he’ll be in Copenhagen to lead the charge. Here’s hoping for gold tomorrow.

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?

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.