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Family vacation, villa rentals - Turks&Caicos, Grand Cayman, St, Martin?

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We are planning a family vacation with 4 generations including 5 months baby. We are looking to either rent a 4 bedroom villa (which is preferable) or condos or resorts that have rooms with kitchenettes so we can have family breakfasts and lunches and go out for the dinners.
We love Turks and Caicos so were looking for something there. But there are not many villas on the Grace Bay or they are too expensive.
As an alternative, we have started looking at Grand Cayman or St. Martin. I only stopped at Grand Cayman and St. Martin when we were on a cruise.
Where on the seven miles beach it is better to stay? Does it matter if it is far from George town?
There are a lot of nice villas for rent in St. Martin around Orient Bay though they are mostly 3-5 min walk form the beach. Are there other good beaches on St. Martin except Orient beach?
We are trying to choose an island which is safe, has nice beach with calm water for swimming, good doctors in a case we need one for a baby and not more that 2.5-3.5 hours from New York city.
We love to swim and walk along the beach. We like when there are dining options in a walking distance though I know that on St. Martin we would probably need to rent a car.

Any suggestions are appreciated. Did anybody has experience renting villas? This will be our first time. We usually stay at hotels. It is so hard to find something decent and not too expensive.

Looking forward for any advises!

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