It's possible to use both certificates under 1 reservation but only if they are from one Hilton account. In your case there are two separate certificates which means you'll need separate accounts to use them, so you'd need to both be Hilton members. After opening Hilton accounts you'd have to make 2 separate bookings; one for each of those nights (one for yourself and one for your partner). Easy.
Have you looked at the T&C of the certificates? It may allow 'gifting' of the certificates to another person or Hilton member but that's not likely.
And regarding your last question. You are staying for a total of 7 nights, correct? In that case:
- I should book 7 nights for standard room with my points (95K points/night)
- No. Only book 5 nights with points
- I will get 5th night free
- Correct
- I should try to use 2 free weekend night certificates for standard room
- Yes, for the 6th and 7th nights
- Once all applies I should try to upgrade it all with cash to overwater villa
- Correct
Everything is legit and above board! Relax!
Sorry, forgot to answer your question
Originally Posted by
MJJW1985
Also any recommendation when is the best time to book the resort? How many months prior the arrival or any recommendation for the month between August - November?
For the booking, do it 2, preferably 3 months out to avoid any disappointment. If you want upgrades, book as early as possible. Don't wait until it's only a month or two out, you could miss out on the WV you want.