Vacation Home Rentals Blog

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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.

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.

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.

Much to my surprise, a few friends have decided to take off to the Indianapolis Colts season opener this weekend–without the kids.

In fact, come September, it’s a yearly tradition they share with their neighbors, who also have minors.

What I can’t get over: How they can sneak in a trip at the beginning of a school year. What? Really? Parents can do that? Assuming you have a babysitter, why yes you can.

For moi, while being in Indy does have its perks (decent drive, but not too far if I needed to rush home), a long weekend in a South Beach condo rental is more my scene. Strolling for eye candy along Ocean Drive, shopping on Lincoln Road and cocktailing poolside remind me of days when Hello Kitty birthday cakes and school supply lists weren’t on my radar.

A long weekend, in this parent’s mind anyway, should be as disparate from your day-to-day routine as possible. A cure to the baby blues? Perhaps a cocktail on the roof at the Mondrian or a couples massage at The Biltmore are in order.

Incidentally, I would be going on the Indy trip, but we couldn’t get a babysitter. So I’ll save my mommy trip for a vacation in 33139.

Sometimes the pool, as in the case of several of our Panama City Beach condo rentals, blows the ocean right out of the water.

Regulars at these resorts love the beachfront access, of course, but the pool is where they wind up spending most of their days. Some highrises have poured millions into their installation. The free-form one above is one of the largest in the Panhandle, a network of bridges, jumping Dolphin fountains, island with tiki bar, plus a hot water jacuzzi shaped like a star.

Think of the hours you’ll spend floating on a raft in circles or lazily wading in the sun.

The area is also blessed with lots of condos that offer gyms, spas, saunas and steam rooms, while some also have indoor pools.

With all that man-made fun, you’ll hardly see your room. Just don’t forget to get the requisite photo by the seashore.

Oh summer, we hardly knew ya.

Do you really have to go? Please grant us one more chance to build a sandcastle or walk on the beach. After the year we’ve had, don’t we deserve it?

If you haven’t taken that summer vacation, here’s your chance: Escape to the state where the season never really ends in a Florida vacation home.

While folks in other states hunt for trench coats and sweater sets, flip-flops and sundresses can be worn well into November in the Sunshine State. So if you missed out on planning a vacation for these last two weeks of August, have faith that you’ll still get to be sun-kissed in the fall.

The Port Charlotte vacation home featured above is one of the best deals seen yet, renting for just $600 a week through Oct. 3. After that, it jumps a mere $50 a week to $650 until Dec. 19. The figures don’t lie. A four-bedroom house–with a pool even–for less than a nightly rate at an upscale hotel.

There isn’t much to do in Port Charlotte but golf or hit the beach, but for those who haven’t taken vacation yet, that would probably suit them just fine.