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Best island for a villa rental

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My family is looking to rental a villa on a Caribbean island in December of this year. We will be traveling with 6 adults (ages: 65, 64, 38, 36, 33, 33) and 3 children (ages: 6, 2, 1) - we are looking for a beachfront location with a pool for a low key vacation (looking to spend a lot of time in the pool and on the beach) - we are looking to rent a 4-bedroom house or condo that is privately owned or part of a resort.
The most important features for us are:
- beach
- pool
- great weather in December (warm/hot and not much rain)
- not too far of a flight (about 4-4.5 hour max from NE US)
- ability to go out (close to safe downtown area - for shopping and dinner)
- golf nearby (for 2-3 rounds during a 7 day stay)
- spa nearby (for a ladies day out)

We are considering: Turks & Caicos, Puerto Rico, St Maarten, Grand Cayman

We have been to every location before kids - I am looking for some advice to help narrow down my island list - if you can provide pros & cons for the islands on my list, I would greatly appreciate it - and if I am missing a great family/kid-friendly island, please let me know. Also if you can offer advice for the best spot to stay on the island, that would be much appreciated too.

Thank you,
Abecker28

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