How I Took My Family of 3 on an Epic 3-week Vacation in Jamaica for About $4,000 — Including Flights

The drive from Montego Bay was supposed to take four hours, but five hours in, it was clear Google Maps didn’t account for the fact that the last 12 miles was an unpaved and potholed single-lane road. 

Our rental car (a little Mazda Demio) and driver (my husband) were tasked with dodging potholes, pulling over every time a vehicle came from the other direction and letting teens zip past on their motorbikes. It was dark and our arrival window for the Airbnb was long gone. Oh, and there was a screaming baby in the back seat.

It was our first trip as a family of three. My daughter was a fresh 6 months, with a brand-new passport, and we were in Jamaica. But as you might have gathered, we weren’t headed to an all-inclusive resort in Negril or Montego Bay, like many families do.

I take great pride in my ability to get off the beaten path and save a buck, and I was determined to not let the fact that I now had a baby change that. Plus, our friend who grew up on the island promised our final destination — Boston Bay, on the far eastern side of the island — would be worth it. 

The almost six-hour journey from the Montego Bay airport to the far eastern coast of Jamaica was brutal, but Boston Bay was the paradise our friend guaranteed. Clean beaches, great surf, and quiet nights. And after a day in the water, the drive was a distant memory.

Here’s how we made this trip happen on a budget, spending a little over $4,000 for three people to spend three weeks in paradise.

We booked flights a month in advance, used miles, and didn’t have to pay for the baby.

Cost: $1,656

In our family, booking last-minute flights is the norm. That, paired with the fact that we live six hours from the nearest international airport, usually means we pay more for flights. However, for this trip, we had two major wins: I had some flight miles, which shaved off a few hundred bucks, and my daughter — who was 6 months old — flew for free on my lap.

We rented a car, which ended up being a major expense.

Cost: $750

We booked the cheapest car on the island from a small rental company. The total for three weeks was $340 — a steal. Of course, like many things that are too good to be true, the online cost didn’t match the actual price. After admitting that, yes, we did need insurance, we forked over $750. It was an unexpected expense, but there was no way around it. We drove the car daily.

We split our time between two Airbnbs.

Cost: $1,010

We stayed in two different Airbnbs during our trip, both in the Boston Bay area. The first had a queen bed and a crib and the second had two queen beds (we utilized a pillow barrier in the latter). An Airbnb was key because we ate breakfast and dinner at home every day — another money-saving tip.

Related: The Best Times to Visit Jamaica, According to Local Experts

We rarely went out to eat, and when we did, it was for lunch.

Cost: Approximately $900

Our food costs were wonderfully low thanks to the fact that there aren’t many restaurants in Boston Bay and we had a little human who needed to be in bed by 7 p.m. For breakfast, we ate yogurt and tropical fruit and did lots of pasta for dinner. Lunch was typically a PB&J sandwich eaten on the beach.

That said, it was ackee season when we arrived, so we enjoyed a few nice meals at Aya Naturals and visited several of the area’s famous Jamaican jerk stands, where jerk cooking was invented.

All in all, we spent around $95 a day on food and lodging, plus flights and a rental car. The total trip cost was $4,316.

We spent a full 20 days in Jamaica, which helped offset the cost of flights and the 20-day car rental. We had such a great time, we’re planning to do it again this fall — this time with a toddler.