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Jason and Courtney have a special affection for Nantucket -- it's where they met and fell in love. They've even chosen the island for their wedding and new home. Their decision has come down to three amazing island properties.

After three moves to different cities, Frederick and Carina decide that what they really wanted was a laid-back place to raise their kids. Their Key Largo vacation memories get them thinking about a permanent island home in Florida.

Eric and Shontae jump at the chance to leave the hectic life of San Francisco to work and live on the laid back island of St. Simons, Georgia. Remembering her childhood there, Shontae is eager for her girls to grow up there, too.

When Chris gets a chance to relocate for work and cut his traveling time, he and wife Laura, who works from home, jump at the chance. They chose Washington's coastal San Juan Islands to live and raise their son.

Adventure seekers Matt and Tom are ready to leave the cold and snow of Chicago for the sun and fun of Old Town in Key West, Florida. After looking at three properties, they are ready to make an offer on their dream home.

Mount Desert Island off the coast of Maine has been a special place to Tracy since childhood vacations. Now, she and husband JC want to make their dream of owning a permanent home and raising their family there a reality.

Islamorada, off Key West, Florida, has the laid back and relaxed atmosphere that Pablo and Michelle fell in love with as a couple. Now they are ready to make it their island home and must decide between charm or construction.

As newlyweds, Nesward and Jackie lived in Alaska for his job with the Coast Guard. After three children and a stint in Hawaii, they want to return to live on Kodiak Island, Alaska, with its distinct seasons and wildlife.

John and Megan enjoy the hip urban life of Richmond, VA, but now they are ready to start living a quieter life closer to parks and the ocean. When a job opportunity comes up on Mount Desert Island, ME, they jump at the chance.

Boston seems far behind to Rob and Suzanne when they take the ferry to Martha's Vineyard for vacations. They hope that by moving there full time, they will find the balance that their hectic and stress-filled life is missing.

Atlanta couple Katie and Jason act on their dream to live and raise their family on St. Simons Island. Having vacationed there as children themselves, they want to put their own roots firmly down in this sandy tropical paradise.

A hectic lifestyle in Ohio left Stephen and Beth wanting more than what their cookie cutter subdivision lives offered. With Stephen able to work remotely, their dreams turned to their favorite vacation memory, Key West, Florida.

Josh and Stephanie have lived near water since they were born, and now that they are getting married, moving to be near water only makes good sense. The beautiful views of Washington State's San Juan Islands are calling them home.

Living in Hawaii as a Coast Guard rescue swimmer, David has an opportunity to transfer with his wife Ashley and children to Kodiak Island, Alaska. They are ready to start an adventurous life in this nature-filled paradise.