Vacation Home Rentals Blog

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Hawaii came in as the second-happiest state in the U.S. in the Gallup Organization’s Well-Being Index, which looked at factors like job satisfaction, emotional and physical health and healthy habits.

There’s no need to state the obvious as to why, but Utah–the leader–is a headscratcher. Utah, really? Utah before luaus, waterfalls and golden sands? No offense to Utah, but I’d rather be surfing, parasailing, tubing in a lazy river, dolphin watching, heck, eating Spam, in a Hawaii vacation rental. Wouldn’t you?

Now it’s time for you Utah folks to sound off.

What is your secret to happiness? Share on Twitter @checkincheckout.

There’s not enough spontaneity in your life.

Your day is a series of deadlines book-ended by trips to the elevator, the office snack drawer and depending what’s on TV, that 7 p.m. spin class. (Your teacher is cute, but his squeaky voice, amplified by a wireless microphone, annoys.)

A crescent beach … a sunset … are just what you need.

Proponents of the unplanned vacation will find a deal in Destin condos, where the Gulf of Mexico waters are still warm and the high-rises are eager to fill their rooms during the slower fall and winter breaks. Florida’s Emerald Coast has some of the most pristine beaches in the state, offering less kitsch (not that Dade County’s Coral Castle doesn’t have its charm) and centralized living that allows visitors to stay in one place, thanks to on-site restaurants, multiple pools, parking, fitness rooms and tennis and basketball courts.

For a husband looking to surprise his bride with a long weekend away, you can’t beat it.

The two of you can also go shopping at the Silver Sands Factory Outlet, snorkeling, para sailing and golfing, then retire to your quarters to watch the dolphins from your balcony. The condo above rents for $100-$150 a night through Dec. 26. Do it. Shock her.

She’ll be impressed for years.

If Ivanka Trump can get married in the fall, then late-year weddings must be the new black. Or in her case, the new lace sleeve. (An impeccable style modernized by Vera Wang)

Maybe it’s the cooler weather or the buildup to the holidays, but brides and grooms are warming up to hosting their big day in October, November and December. But not everyone has a Trump-sized budget.

Perhaps you’re one of those couples who recognizes the importance of the union, but you’d rather save your dollars for a splashy honeymoon or first home. Smart.

It’s just one day, right? One day that can equal $$$.

When it comes to the honeymoon, Mr. and Mrs. have a bounty of affordable options in vacation home rentals. From Florida vacation rentals to Cape Cod house rentals, there’s a hideaway for every bank account. Had to cut 50 of your closest friends because the numbers weren’t working? You’ll forget the guilt when you’re tanning poolside in your Miami Beach vacation condo or testing the sauna in that Utah chalet.

In rough economic times, road trips shouldn’t  be out of the question or staycations in your very own zip code. With added baggage fees on major carriers, both may be the ways to save airfare for other costs like entertainment or the occasional meal out.

And if you’re newlyweds who simply don’t have enough vacation time accrued to take that getaway of a lifetime, consider a long weekend or “teaser” honeymoon. Save the sightseeing for another time. This is one case where its OK to spend most of your time in the room.

Tonight’s tomfoolery–MJ, the Gosselins and Gaga oh my!–will have all of us thankful for that extra hour of sleep, but in some places, daylight savings time isn’t practiced.

In territories and states like Puerto Rico, the Virgin Islands, Hawaii and Arizona, residents don’t need to turn their clocks back. If you’re spending Halloween in a Hawaii vacation rental, your location’s tropical latitude ensures plenty of daylight in whatever season.

Lucky Hawaiians.

What is it like to be spoiled with so much sun?

From State College, Pa., to Rochester, Minn., the cold has reared her frosty head. Winter has come early, and folks aren’t happy about it.

Well America, it looks like it’s going to be a long, blustery season, so it’s time to think about that warm weather vacation ahead. Counter seasonal affective disorder with thoughts of the other powdery stuff: the sandy, er, rocky beaches of California.

Now is as good a time as any to reserve your California vacation rental.

For you lucky Bostonites, flights on Virgin America are going for as little as $100 each way to Los Angeles if you purchase your ticket by Oct. 27. And why wouldn’t you want to? That white stuff during last week’s Patriots-Titans game wasn’t your TV on its way out–it was a blanket of snow, and the Pats’ earliest snow game on record, according to a FOXNews.com report.

Sure, it’s cool and pretty initially, but come January, when all the holiday lights are down and the roads are left a hard, slippery, grey, slushy mess, a weekend in California will be calling your name. Do it. Your UGG boots will need a rest.

Actually, lemme take that back, the California beach rental pictured perches over Monterey Bay, one of ForbesTraveler.com’s prettiest towns in the U.S. A total of 20 made the annual  list, including Union, Wash., Annapolis, Md., Sedona, Ariz., and Lake Placid, N.Y.

The feature sparkles with coastal communities, postcard-perfect Main Streets and desert diamonds. What strikes me the most about each of the selections is just how authentic the cities are: There is nothing chintzy or feels-like-a-souvenir shop about them.

Every city is its own distinct haven, a hometown for all to enjoy its hillside houses, charming downtowns, nature walks and breathtaking views of mountains, lakes and surf.

Monterey, a town rooted in the sardine canning industry, ran away with a ranking thanks to its rich marine history and award-winning aquarium. Cannery Row serves as a shopping, dining, lodging and nightlife hub for all who seek to be near the marine sanctuary and perhaps catch a glimpse of the sea lions at play.

What do you think? Are there any glaring omissions from the list? Let’s discuss on Twitter @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.

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.

Since we had so much fun talking about ghosts yesterday, here’s another city for a scary getaway: Key West, Fla.

Margaritaville is notorious for its checkered past, from voodoo practices to pirates. Ernest Hemingway, who spent more than a decade there, liked it so much he reportedly is still hanging around. (Then again, if you’re going to be haunted by anyone, how cool would Hemingway be? Surely he’d be more friendly than the Lady in Blue, who was hung by an angry mob after she sliced up her husband and two boys, as legend has it. Supposedly she still lurks at Captain Tony’s, also a favorite bar of Hemingway’s, near the tree where she died. At the very least, you could chat with Mr. H about his books and offer him a mojito, his cocktail of choice, to bribe your way out of torture.)

I’ll leave it to the professionals at two tour companies–The Ghosts & Legends of Key West and Ghost Tours of Key West–to take you ghost hunting at landmarks like The Otto Mansion, the old city morgue and The Heritage House Museum. Personally, I’d rather be on the beach with a good book, say “The Garden of Eden,” or sitting in a Key West condo rental with my lost shaker and salt.

In the end, the IOC chose the sexy Brazilian newcomer to host the 2016 Summer Olympics: The girl from Ipanema.

Rio de Janeiro will be welcoming the world’s athletes to the games in 20 years, and while we’re disappointed here in Chicago, at least we lost to a formidable contender.

(Shoot, having lost the battle in the first round of voting, with just 18 of the 94 yeses secured, were we ever really a competitor?)

Let’s not focus on our nickname as Second City, though. What awaits in Rio are peepshow beaches, thrilling nightlife (This is the home of Carnival) and a hair-raising passion for sports. Chicago may have brought out its triple Os–Michelle, Barack and Oprah–but Brazil had a superstar as globally known in Pele.

Rio de Janeiro vacation rentals will emerge as overflow options–or if travelers are smart, alternatives to hotels–for international visitors. VacationHomeRentals.com lists some 34 vacation condos, like the spanky one above–close to the beach. Would it be wise to look now? Meh. You’re probably safe to wait until at least 2010, but it wouldn’t hurt to stroll around the site to familiarize yourself with the properties.

And if for some reason 20 years isn’t ample enough time to save for a South American getaway, there’s always Chicago vacation homes. Summer is when the city dazzles.