Buy Your Own Island, a guide to lifestyle design by Danny Flood.

This post is an excerpt from the new best-selling book, “Buy Your Own Island.” The most thorough and comprehensive handbook for lifestyle design and the mobile lifestyle on the planet, the book outlines how to travel the planet using strategies such as housesitting and much more. You can download it immediately from Amazon, or download the audio book for free by clicking here.


The How-Tos of Housesitting

The internet is your best friend when it comes any modern lifestyle design pursuit, and housesitting is no exception either. Housesitting is another great way to subsidize your adventures, and unlike most other options it is seriously overlooked and under-utilized.

Housesitting is great for couples to travel together!

Want a free condo in Brooklyn for two months? How about a beach house in Nicaragua, or a villa in the Italian Alps? Housesitting, combined with the Internet, allows you to take the locations you’ve always dreamed about living in and places them at your fingertips. Literally.

Unlike CouchSurfing, you can pick a location and stay for an extended length of time – from one or two weeks to a few months. Plus, it’s a great way to “reverse geo-arbitrage.” Many independent lifestyle designers choose to live only in certain hubs where their first-world currencies go the furthest. But by housesitting, you can save BIG even in expensive, developed countries by getting free rent, a kitchen to cook in, and other amenities (sometimes even a car!). You also get that feeling of “home” and get a taste of the local scene in ways that most travelers never will.

Housesitting is nothing new, and has been around in some form or another for many years. While in the past limited generally to neighbors and friends, it’s found new life in the exciting power of the internet to connect people from every corner of the globe. As of today there are over twenty housesitting websites that connect homeowners with housesitters. Most of these websites are international, although some are heavily or entirely-focused on certain regions or continents.

Housesitting is possible because housesitters provide an important role to homeowners. A responsible housesitter allows a homeowner to take longer vacations and more of them. Housesitters also help keep homes safe while the owner is away and a dedicated housesitter is more reliable than a neighbor. Seventy-five percent of all housesits involve pet care of some type. More than anything, a housesitter provides peace of mind to the homeowner so that they can enjoy their vacation.

In my opinion, the three best housesitting websites to find a successful housesit are:

1) ($50/year)
2) ($20/year)
3) ($60/year)

You can get started right now. Simply choose a site(s) and sign up. But in the same way that finding hosts to couchsurf with can be difficult, obtaining a successful housesit is no cakewalk either. There may be tens or hundreds of other people applying for a housesit. Competition for housesitting opportunities can be fierce! But just like anything else, there are ways to stand out from the crowd and dramatically improve your chances if you know what to do.

How to Obtain a Housesit

Successfully finding a housesit is similar to finding a couchsurf. It requires a great presentation of your best self, persistence, excellent communication and interpersonal skills, and a touch of common sense.

Create an outstanding profile

A true lifestyle designer can never skimp on creating a great profile. Each online profile represents our brand, and profiles are the lifelines that enable us to live this type of lifestyle. Just like your CouchSurfing profile, the more information you fill out, the better.

Spend some time looking at other housesitter’s profiles, and you’ll get an idea of what a great profile looks like. It all comes down to showing potential homeowners what they are looking for. Remember, your profile is like a resume, so you want to put any and all information that may matter to homeowners. Focus on the homeowner’s needs, not your own. Point out what you can bring to a housesitting assignment. Do you know how to care for a cat? Do you have experience in gardening or home improvement projects?

Choose a few of your best photos to include. Show bright, happy photos of your face. Don’t include photos of you in a skimpy halloween costume or any that involve you holding a beer in either hand (San Diego, where I’m from, is the brewery capital of the US, and you’d be surprised how high a percentage of San Diegans’ photos include one, two, or several beers in them). Do include photos of you with any pets, since most housesitting jobs involve petsitting.

How to E-mail and Get the Gig

On most housesitting sites, homeowners will place “adverts” seeking housesitters. It’s rare for homeowners to start a search by contacting housesitters directly (unless it’s someone they’ve used in the past). On some sites, you have the options to receive notifications when new adverts are placed, and you can even select certain target countries or cities.

When you get notice of a new advert that seems like a good fit for you, respond quickly! If you’re one of the first members to contact the homeowner it will improve your chances that your e-mail will be read and responded to. Including any and all pertinent information in the initial e-mail is another way to stand out and reduces unnecessary back and forth for the homeowner to get information to make a decision. In your opening e-mail, include a selection of your best references.

If you really want to stand out, record a video with your computer’s camera and appeal to the homeowner directly. Upload it to Youtube with the unlisted privacy setting, and email them the link. This will give the homeowner a much better idea of your personality, it shows a little extra effort and initiative, and improves your chances of being accepted.

Just like couchsurfing, it’s all about finding some common ground with the human being you’re reaching out to and building a strong rapport. And I’ll say it again: always remember to focus on the other person and their needs!

Once You Arrive

House sitting services guide for housesitters.

You arrive at the housesit and meet the homeowner in person for the first time. This is the “handover period” where you and the homeowner get to know each other. You want to also get to know the home, neighborhood, and be clear about all of your responsibilities. Collect important information about the household such as garbage pick-up days, how to set and disarm the security system, and the location of electrical breakers. If tending to a pet, ask about the pet’s feeding routine, medication and walking requirements, number for the vet, etc. If tending to a garden, ask about the plant watering routine and necessary tools. Find out if there is an emergency contact, whether anyone a spare set of keys, and if there are any neighbors you can contact in case something goes awry.

Be clear on what needs to be done should an emergency occur, and what the homeowner expects in terms of communication. Some homeowners will want to be contacted at regular times, and some prefer minimal communication. Depending on which housesitting website you use, you should also be provided with a housesitting agreement to go over with the homeowner and sign.

Once the homeowner has left and your housesitting job has begun, you are on your own. There will be a host of responsibilities that you will be expected to tend to. Be clear are on what these are before the homeowner leaves, and be an ideal guest and responsible caretaker while they are away.

Get Your Feet Wet

If you’ve never housesat before, how would you start? My advice is to start local first. Offer your services to friends and family who own homes in other cities besides your own. Post to your social network that you’re looking for a housesitting opportunity. You never know what may happen. You could even set up a simple website or blog using WordPress to advertise your services. For one example of this see:

Camp in someone's garden!

Other Unorthodox Accommodation Options for Travelers

You only live once, right, so why limit yourself? If you’re the type that’s willing to try anything once, then keep reading. On the following pages are a couple other unorthodox accommodation options that are worth looking into.

Camp in My Garden

Camp in My Garden for hosting travelers.

For the rugged individual looking to do something different, you could also consider “camping out” in someone’s garden ( Most of the available garden campsites are available in Europe, with an especially high concentration in the UK. You can search countries you’re interested in traveling to, and use an interactive Google map feature with location icons to click on properties and get more information. You can get general information about the property and homeowners, see the available facilities, and contact the homeowner. Really cheap way to travel Europe (many locations are available for under 5 Euros a night). Something I personally have never tried but probably worth doing at some point.

Warm Showers

Warm showers accommodation for traveling.

“Warm Showers” ( is a site similar to CouchSurfing that caters to long-distance cyclists.  There are over 25,000 hosts on the site who can offer everything from a bed, to food, to laundry service to touring cyclists.

Negotiating with Innkeepers

Sometimes if you visit a guesthouse or a small, independently-owned hotel, you can negotiate a free or low-cost place to stay. Simply explain to the innkeeper that you’re a traveler and have very little money to spend – and ask if they have a sofa or even a sleeping bag or anything – and people will often help you. Be cordial and polite, and offer to help out in any way if needed. Best case scenario, they’ll have a sofa or a mattress for you for free or minimal cost. Worst case, they’ll recommend another place where you can try your luck.

Just don’t expect the Buckingham palace. And don’t take your iPad out afterwards and wave it around in front of them after they give you a deal.

I traveled through Vietnam during the week of Tet New Year and everywhere I went accommodations were booked because all of the Vietnamese were on vacation. But one innkeeper gave me a mat, blanket, pillow, and mosquito net to sleep under. Another gave me a mattress and my own room – a sauna.

My deluxe sauna room in Da Lat.

My deluxe, one-of-a-kind sauna bedroom while in Da Lat.

I have a British friend that I met on the road named Ben who, at the tender age of 18, managed to hitchhike from one end of Baja California to the other without any money. He did what he had to, relying on the kindness of strangers, and people helped him. We’re brought up to be so reluctant to ask for help – it’s almost like admitting weakness. But most people are willing, and want to help, if you ask them.

And by the way – having “little money to spend” doesn’t have to mean that your bank account balance needs to be teetering near zero. It could simply mean that you’ve set aside a budget for your trip that you’re trying to keep within. During a recent overland trip through Mexico, I resolved to only bring a few hundred dollars of cash, and travel as frugally as possible. I had plenty of reserves in my bank accounts – but I wanted to keep that money there for when I returned home. Frugality is a useful skill to acquire, and setting and keeping within a budget is a good thing to practice.

Trade Services for Room and Board, work exchange for travelers and hosts.

WorkAway is an awesome resource which allows you to connect with hosts around the world with whom you can trade your services. However, it can be very competitive because the website has a high number of users and there a ton of volunteers approaching each potential host.

If you’re traveling for the long-term, it is actually very easy to approach a few hostels or BnB’s directly and offer a trade in exchange for a place to sleep for one or two months. You can negotiate a long-term stay, and cut your expenses to virtually nothing. I’ve done this on several occasions.

Almost unanimously, these establishments need help with their website and their online marketing. If you take an evening to teach yourself how to set up a self-hosted WordPress website (I have a WordPress training program with videos that you can check out at, you can help these people set up a website or blog in exchange for a free bed. You can literally design a website or blog for them within 2 or 3 days: you simply register the domain, add hosting, set up a nice theme, then add content and graphics.

You’ll earn their gratitude, and save quite a bit of money in the exchange. If you do good work and are familiar with online or social media marketing, there’s also a good chance that the owner may hire you to help with their marketing. If you do this right, it can pay your way as you travel long-term around the world. Simply work with a different hotel / hostel / BnB in each location.

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