When a Monthly Vacation Rental Makes Very Good Sense

A monthly vacation rental? In your dreams! You’re lucky to manage a week away, right?

That puts some very desirable beach communities out of reach. In Sanibel Island, Florida and Carmel-by-the-Sea, California, for example, the majority of vacation homes only rent by the month.

I’m going out on a limb and suggest that maybe you can swing it. Here are two good reasons to ask yourself why not a monthly vacation rental?

Extend your vacation to a month? Yes, you can!

1. Work from the beach.

If you already work from home using a computer, high-speed Internet connection and telephone, why wouldn’t you be able to do the same work from a monthly vacation rental home?

2. Test drive living in paradise.

If you’ve been itching to find a place with less stress and many (many) more sunny days to raise your family or spend your retirement, you could be among the estimated 40 million who make the move (according to a book I just finished called The Geography of Bliss). Renting for a private home for a month -- or more -- is the best way to test-drive a permanent move to paradise. A monthly vacation rental is a great place to live like a local!
How A Monthly Vacation Rental Helps You Extend Your Vacation -- Without Overextending Your Vacation 'Credit'

If you only have seven days of vacation, you have to work hard to cram everything you want to see and do -- plus travel to and from your destination -- into that short timeframe. When you return home, it can take the better part of a week to get back in the groove. By the end of that first week, you’re thinking “What vacation?”

See the irony?

But what if you had a month to see and do everything on your list? If you open your mind to that possibility, the benefits multiply.

Monthly vacation rental rates can be surprisingly affordable.

Toucan House on Sanibel Island, Florida has three generous bedrooms and lots of outdoor living space, including two lanais and a deck in 1,900 square feet. Yet it rents for as little as $2,500 in the off-season. Less than $100 a day for six people!

A reasonably priced two-bedroom condo (with no private outdoor space) will cost you over $500 for a month.

Time is precious.

The luxury of having more time will take away that frantic feeling that makes you start throwing money at your vacation to milk every ounce of fun out of this precious window of time that (you keep reminding yourself) won’t come again for another six months.

Wi-Fi is, well, simply magic.

Instead of scrambling to make your plane at the end of the first week, you’ll be easing back into work. (You’ve already been checking e-mail.) Most vacation homes have Wi-Fi. Many include unlimited long distance calling. With the blessing of your boss, you can be just as productive working from a monthly vacation rental by the beach as you could working from your own home.

In many ways, a flex-cation trumps a vacation.

The beauty of working from home is flexibility. So, really what’s the difference between sneaking in some errands in your own neighborhood and enjoying a walk on the beach during lunch? With approval you might sprinkle work days and days off or flex your schedule by getting up early to call clients or co-workers.

If you lighten your workload by mixing work into your extended change of scenery, the dreaded backlog of e-mail, voicemail, requests, project status reports, and the rest -- the wall of extra work that makes you wonder if going on vacation is worth the catch up -- shrinks. Or disappears.

If you already work from home, even part of the time, you’ve got precedent for working in a monthly vacation rental. Lay out a reasoned plan, noting when and how you’ll be available and what you’ll be accountable for. Research and agree on a plan B if things go awry. (Say a hurricane takes out the power.) It’s probably a good idea to limit the number of people you tell about the special arrangement to put a lid on envy.

2. Stake out your space.

Make sure the monthly vacation rental you book has a space that works for you -- a semi-private space where you can spread out and be comfortable and productive.

3. Bring props.

Music, a lumbar cushion, a stress ball -- whatever you need to make your office in the private home you’re renting by the month feel like your home office.

4. Line up locals.

Ask the vacation rental owner or manager to recommend local services including highly rated technical support people, mail services like FedEx and well-stocked office supply stores.

5. Relax.

Forget the “work hard, play hard ethic” -- it’s so last decade. Let the change of scenery and relaxed vacation vibe in a monthly vacation rental feed your productivity.

You may also want to keep an eye out for local business/work opportunities, in case things go so well you decide to pack up and move here.

Beth and Jim: Trying on a Better Quality of Life

Beth and Jim with Amy and Brodie

The goal: Break from the stress of a long commute and unfulfilling job and build a better quality of life for their family of four -- including two home-schooled children, ages 8 and 13, and the family dog.

The vision: “We were looking for a small town community that wasn’t small town—that had some culture,” Beth says. “We go to church and
wanted a living breathing exciting church like ours in Baltimore. There’s a great church community here and that was a huge part of our decision. We wanted to be near ‘stuff’. We love the wildlife on Sanibel and we can go to Fort Myers and get whatever you need or want and you have access to the airport and city and shopping. And, really, just about everything you need is here on the island.”

The plan: “Vacationing somewhere and living there are often two different things,” Beth says. “Our plan was to book a monthly vacation rental for three months. We were going to try to spend about a month just settling in and seeing how we felt about hot summers and bugs and the community. We decided from the get-go that even if we hated it, or decided it wasn’t what we thought it would be, it would still be a nice vacation. Our worst-case scenario: we came down and enjoyed three months on Sanibel and went back home.”

What happened: Lots of fun, along with some trial-by-fire. “Toucan House was a great home base,” Beth says. “You can walk to the beach and bike all over the island on 30 miles of paved paths. The entrance to the Wildlife Drive in J.N. "Ding" Darling Wildlife Refuge is just four miles from the house. The end of the wildlife viewing loop comes out at the entrance to the neighborhood where we were staying at Toucan House. We bought a federal Duck Pass and every time we came home, we’d detour through there free instead of taking the main road.”

During their stay, a Category 4 hurricane and two tropical storms barreled through. “We decided we’d seen the worst of it and we still loved it,” Beth laughs. “After about a month, our kids were done with the vacation thing. So we started looking to buy.”

Bottom line: “We’d always go away to these vacation spots where other people were living the life we wanted to be living and we got to a point where we thought, ‘Why can’t we do that too’? We waited until the right time in our lives. It was kind of the perfect time to jump because our kids weren’t into the high school groove yet. But they were old enough.”

With the kids settled back into home schooling, Beth and Jim found new gigs on the island. Jim started a computer consulting business and has become the local computer guru for small businesses owners and returning sunbirds. Beth works part-time for her favorite clothing store, Fresh Produce.


Inge & Gus: Adopting a Winter Haven for Retirement

The plan: Gus and Inge’s love affair with Sanibel Island started with a day trip. “We decided to spend a month here (in a monthly vacation rental) to see if we really liked it for daily living,” Inge says. The next year they rented for two months. The third year was the charm: “We planned to rent for three months and that’s when we bought,” she says.

What happened: During each visit, the pair took their time settling in. They joined the library and Inge volunteers at the Sanibel-Captiva Conservation Foundation.

On daily bike rides the couple chatted with locals who were happy to share their experiences living on the island. “We didn’t feel rushed. It gave us time to explore and get a lay of the land. I think I explored every neighborhood on the island before saying, ‘Yes, I like the one we’re staying in now. It feels right,’” says Inge.

Call it luck or kismet -- the couple’s new home is virtually across the street from Toucan House, the monthly vacation rental they rented for three years!

The bottom line: Today, Inge and Gus spent half the year on Sanibel Island. “I think a monthly vacation rental home home exposes you to the area, the people and amenities more than staying in a hotel or a condo because you’re out in the open. You relate to people in a broader way than you would in a hotel,” Gus says. “I can’t think of a better way to make the transition.”

In a state full of sunny beaches, Sanibel Island, Florida, has proven to be an ideal fit for these two former world-travelers. “It’s a pretty unique little place,” say Gus. “We have a pretty broad range of foreign visitors -- French, German, English, Spanish -- who are interested in wildlife conservation and did the same thing we did. There’s a real cosmopolitan feel, even though we’re all dressed in shorts and tee shirts and sandals.”

2. Get out and about -- and listen. “Exploring on a bicycle gives you a whole different picture than riding around in a car,” Gus says. “The people we met who were out gardening invited us back for drinks. We got a much better feel for the type of people who were already living there and we also got inside information on Sanibel’s neighborhoods. Once you tell them you’re buying, boy, they come out of the woodwork with help! Our neighbors helped us with all kinds of recommendations.” 3. Get involved. One of things Inge and Gus love about Sanibel Island, Florida, is its active community. “There’s more of an interest in doing vs. going out and dressing up,” Gus says.

“There’s a lot of intellectual power here,” adds Inge. At Monday morning current events discussions, “you had better have read The New York Times.”

4. Face the flaws. Inge and Gus visit during high season when the local population swells from 6,200 to 21,000. “You really have to plan that you’re not traveling on and off the island during certain times of day. There are two main roads, so the traffic can be horrendous.”

As prospective year-round residents, Cindy and John wisely choose the off-season -- three months squarely in the middle of peak hurricane season. They wanted to know exactly what they were getting into. And even in the middle of paradise, “If you’re working, it’s still real life,” says Cindy. “Your plumbing still falls apart. Your kids still get sick.”

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