Vacation packages vs. booking hotel and air separately

Recently we've been coming to Negril every other year or so. We've always used Orbitz or Expedia to book our vacation. We're planning a November 2018 trip for 14 days, and I was wondering if anyone could give me any advice on whether it's more economical to book the package with airfare and hotel or to book them separately. Also, we don't do AI, or any of the bigger hotels, just something small on the beach. We've stayed at Legends a few times and Negril Palms. Any advice would be greatly appreciated!
Thank you!

Like you we do not do AI, and have used Orbitz and other like services, along with booking separately. I check both ways each year and whichever happens to be cheaper is the one I use. Right now with the price of Airfare it's been cheaper to book through a service like Orbitz so that is how I am booked now. My '16 and '17 trips were booked separately.

It has been my experience that booking the room direct with the resort is your best bet, as sometimes you can get a loyalty price break. The flights are always all over the place so I book our flights when I see a really good price and usually book those separately each way. Have booked home from jamaica with no ticket there until December, and we always go in February. I use the hopper app to watch the prices for me. Skyscanner is another good app for watching flights. You can have the, watch a return trip as well as each way. ThT being said, I have found some sweet deals on Expedia, it's all in the timing.....

I usually book separately, hotel(s) first then flights. This year (I've been looking since October for a March flight) the prices are exorbitant! Way more than I've ever seen in the past several years. I finally booked my flight last night when I saw they were 200-400$ less than whats been shown for the past 3 months. Still pretty expensive but c'est la vie I didn't want to leave it until last minute. When I've been researching vacation packages I've found the prices comparable to booking separate. I agree with hey_mon...its all in the timing and it takes quite a bit of time to do the research for the best deal. Worth it tho!!

I think it also depends on the hotel. If you're a regular at White Sands, they'll give you a returning discount if you call them directly. I also think that the 'Expedias and Orbitz's of the world' bundling of flight and hotel is a mirage and no true savings. If you don't have a fav hotel, you're better off using trivago (which hits many sites for hotel prices) and booking a room separately.


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Someone told me that the booking sights take a percentage of the rate to "pay" for their service... thereby leaving some great local hoteliers with only a portion of what you actually pay for the room, if that is in fact true (NOT trying to start rumors).

I prefer to book directly with the hotel and airlines.

Thanks! I did book separately this time. Airfare is high, but what can you do? Also, White Sands has been more than accommodating by offering a great discount if I book and pay in full! Haven't stayed there before, but am very much looking forward to it! Thanks for all help!