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Insider, Bermuda for Extended Stayers

The Beginner’s Guide: Where to Buy a Vacation Home

9 minute read

The vacation home lifestyle is the dream for a lot of people. So, to live the lifestyle, you need to find and purchase property in a location right for you. In short, you should put just as much thought into buying your second home as you did your first.

Do you love the idea of being able to escape to your paradise whenever you want, knowing your favorite accommodation will be waiting for you? From European escapes to island getaways, this beginner’s guide will help you identify where to buy a vacation home perfect for your desires. 


The Hamptons: New York’s Rivieravacation home in the hamptons

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The Hamptons are a collection of different seaside communities and are always a popular hit when it comes to summer vacations. The Hamptons is home to long stretches of beach and stunning 18th-century architecture.

East Hampton is home to high-end restaurants, bars and designer boutiques - the perfect luxury to have on the doorstep of your condo. Famed for its celebrity lifestyle, with that prestige comes the price tag. Seaside properties in this area are the ultimate luxury and if your budget allows, it’s a great close-to-home vacation destination. 

Spend glorious hours in the sun while being waited on, being brought the tastiest shrimp skewers, hot dogs and lobster rolls. However, if you’re looking for all-year-round sunshine, the Hamptons only offers a short season. June to September are the peak months for warm temperatures.

The Hamptons are decadent but it’s important to note the seasonality of this location. While Labor Day opens up everything to enjoy, many activities and hotspots close during the off-season. This is fine for those who have the budget to purchase a vacation home outright here, but for those in a timeshare or fractional ownership,  you might not be able to secure the best time in this sought-after destination.

Greece: European Escape

greece vacation home

Greece is a well-loved vacation destination, known for its myriad of unspoiled islands, crystal clear waters and iconic Mediterranean architecture.

Property ownership in Greece is incredibly common as 80% of residents own their homes thanks to a strong culture of family and inherited property. Despite a large number of homes taken, there are still plenty of opportunities to snap up a little piece of paradise as your own.

While EU residents will run into almost no restrictions purchasing property on the islands, non-EU residents will need evidence of both their connections to the country and their intent for property use. 

The cost of property in Greece is largely dependent on the type of property and where you’re looking to buy. For example, a 4/4-bathroom property in Athens can set you back €1,000,000 ($1,182,849 USD).

Greece has recently been through some tough times, but it’s recovering and it’s a well-known fact that tourism doesn’t stay down for too long. You can expect this lovely country to thrive again, attracting tourists and investors alike with its mesmerizing landscape. Through a wider lens, it’s clear the housing market is on the up and this historic destination is perfect for those looking to reconnect with their Greek roots.

Canada: Mountain Retreat

whistler canada buy a vacation homeImage credit. 

Nestled in the mountains of British Columbia, Whistler has consistently been rated the number one ski resort in North America. If you’re looking for a cooler destination that has world-class skiing, snowboarding and mountain biking, this is your vacation home location.

For the adrenaline junkies among us, Whistler has the highest vertical drop in North America; over 8000 ski-able acres of terrain and enjoys more than 11 meters of snowfall each season. The resort offers over 200 runs accessed by 37 lifts.

Seafood in Whistler is excellent due to the close proximity to the ocean, with fresh sushi always being a popular choice. If the high-octane life is for you and your ideal vacation is spent in the brisk mountain air, Whistler needs to be high up on your list. 

Though Whistler is certainly popular, there are vacation homes for a range of budgets. At the lower end of the market, you can purchase a ski-in-ski-out condo quarter share (meaning you have quarter ownership of the property and can use it one week each month).

In winter, the town almost triples its population, with young people flocking from all over the world to call this winter wonderland their temporary home.

Brazil: South American Adventure

Fortaleza vacation home destination for purchaseImage credit. 

With such an immense surface and amazing landscape, Brazil has a lot to offer when it comes to both tourism and the real estate market. As it’s so diverse, it has a wide range of options for those looking for a vacation home.

There are all kinds of interesting regions in Brazil, but one of the most frequented by tourists is the coastal region of Fortaleza. It’s a beautiful city that gives you the true Brazilian cultural experience without making you feel like an outsider. The Brazilian coastline and the nearby towns are the hubs of tourism for the entire country - you won’t have to drive far to be in the thick of it. 

Even though Fortaleza is a thriving tourist hub, the majority of the population speaks Portuguese and may only have a rudimentary understanding of the English language. However, most of the locals are pretty good at communicating where the best places to eat, drink and enjoy are. 

Brazil is the perfect ground for buying a vacation home since the Brazilian Real is a weaker currency compared to the USD or Euro. There are no restrictions on foreign property buyers who are purchasing urban land, beachfront properties, houses or condos. Foreigners have the same rights as Brazilians and residency isn't required.

The market is currently in a slump because of the COVID-19 outbreak but will most certainly rebound as things normalize.


Bermuda: Island Getaway

bermuda island getaway buy a vacation home

We understand currency fluctuation is one of the biggest risks with purchasing properties right now. Bermuda’s Dollar is pegged like-for-like with the US dollar, so you can even use US dollars there if you wish. 

The island of Bermuda is undoubtedly exclusive and purchasing a vacation condo can give you access at a much lower entry price. This welcoming destination has amazing beaches, incredible views, intriguing history and an amazing culture you’ll adore. 

Modern infrastructure makes living in and visiting the island of Bermuda safe, easy and convenient too. It’s becoming somewhat of a bolthole for US citizens, especially with its recent reopening and welcoming of visitors. Bermuda has earned a global stamp of approval for the way it proactively handled the COVID-19 pandemic. 

The island is also well underway in developing a Fintech ecosystem, which will allow Bermuda to become a real leader within this modern technology. 

Whether you want to have a more permanent vacation getaway, make strolling down pink-sand beaches a daily occurrence or have a place to work on your golf swing with uninterrupted ocean views, you’ll find it in abundance in Bermuda. 

Bermuda is perfect. Did we mention it’s only a two-hour flight or less from the East Coast of the US?

Wherever you decide to purchase, work with a local Real Estate Agent who is familiar with the country's language and laws to ensure you know what to expect, comply with local regulations and protect yourself from any unwelcome surprises. 

Many delightful destinations beckon you to buy a vacation home, but have you considered an island escape to break away from city life?

Your Dream Destination Is Waiting to be Discovered

From the stunning beaches of Bermuda, famous for their pink-sand, to the culinary capital of the Caribbean with its glorious seafood, we’ve compared the most sought-after locations, making it easier to find a second place to call home. 

There are definitely concerns and considerations. That’s why we created the ultimate comparison guide. We cover visas, things to do when you’re there and even travel regulations and restrictions to know about - we have everything you could possibly need to know about the location of your dream vacation home. Download your copy below.

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