A New York real estate agent wants to ditch the constant grind of the Big Apple for sunshine in Sosua, Dominican Republic; although she can't swim, she hopes to find a home close to the beach with a pool and a mango tree.

A family looks for a home in St. Croix with a beach view and while he wants a condo with no maintenance, she wants a home with lots of outdoor space for the kids.

A couple expecting their first baby in just a few months wants to buy a home on St. Thomas and he's looking for a move-in ready condo, while she would like a single family home with island charm.

A couple is looking for a home with a lot of space for visiting family and he wants to be next to a marina, but she's more interested in panoramic ocean views.

After vacationing on St. Maarten for years, a couple wants to make the island their home, but they both have strong views about what they want and need to choose how much work they're willing to put into a property.

After opening two hotels on St. Croix, a couple is seeking a place that's close to the beach and he doesn't mind a fixer-upper, but she wants something move-in ready.

A Southern couple trades the country roads of West Virginia for the beautiful beaches of Vieques, Puerto Rico; she's looking for a place close to town that's turnkey, while he wants a fixer-upper that's more remote and private..

A Florida family is moving to Roatan, Honduras, to return to their roots; they agree the home must have room for their two sons and have stellar water views, but he wants something modern while she's looking for traditional charm.

Two divorced best friends look to leave Chicago for the beaches of Cabarete, Dominican Republic; they plan to open a fitness retreat together, but have different ideas of what to spend and what amenities matter most.

A couple wants to escape Canadian winters with a move to Utila, Honduras; they both want space for their kids to visit, but while she's looking for a move-in ready home close to town, he's open to remote properties that need work.

An active family going to Vieques, Puerto Rico wants a home with plenty of room, but he wants to be close to town and she wants something in a rural setting with a big yard.

A newlywed couple is ready for a new life together in St. Thomas; they're looking for a three-bedroom home with a rental unit and her heart is set on solitude and expansive views, but he knows that will come at a cost.

A conservation biologist convinces her husband to buy a home on St. Thomas; they're looking for a place that's private with ocean views, but he wants to consider turnkey condos while she wants a single-family home.