My personal and humble opinion is that you should stay somewhere local – not a resort. Sure, resorts employ a lot of people, but the bulk of the money you spend is going straight back to the United States, UK, or whatever rich country owns that monstrosity of a property. Villas are just as luxurious, but the money stays in the community.
You could also try boutique hotels, Airbnbs, and there are a few hostels on the island if you’re on a tight budget.
A good place to start when finding a villa is VRBO, but be aware that the price listed isn’t always the grand total so just make sure you ask lots of questions before booking. More on this below.
Where I Stayed
Silver Sands, Duncan’s Trelawny Parish
45 minutes East of Montego Bay
This was the first of three places I stayed and we fell in love with it immediately. But how could I not? It’s a luxury villa in a gated community complete with a salt water pool, hot tub, both outdoor and indoor showers, 4 bedrooms, as well as a cook, cleaner and butler. It was a 5 minute walk to the beach and a local fishing village.
It’s owned by a friend of a friend, so I can confirm the owner is Jamaican.
The butler, Willy, was super warm and welcoming. He answered every question we had and more, was always keen to help the women in the kitchen, and was sure to introduce us to all the traditional Jamaican cuisine. He also connected us to a friendly local fisherman who took us out on a little boat to go snorkelling.
Contact me if you’re interested in more information or booking the villa. I can put you in touch with our great hosts!
20 minutes from Port Antonio, on the Blue Lagoon
This was the only “hotel” we stayed at, but it was more like a magical treehouse wonderland. It’s definitely a little difficult to access so be prepared for some bumpy roads, and a lot of stairs once you’re there. You want breakfast? Stairs. Blue lagoon? Stairs. Forgot something in your car? Stairs.
But it’s WORTH IT! If you’re going to splurge on one night of accom in Jamaica, look no further.
Not only do you get an epic wooden treehouse on the side of lush rainforest hill, you get private access to the blue lagoon where you can swim and kayak. It looks like it would be mosquito/spider heaven but we didn’t see any – just a few cute geckos on the walls who are clearly doing their job. There are small boat tours that head out to deeper water to find giant sea turtles, but we didn’t have time to make that happen or we would have.
It’s out of the way (especially if you’re following our route) but I think one night here is enough. You could definitely stay longer but it’s quite secluded so unless you’re looking to relax for a few days and not do much, a quick visit for a beautiful space and a dip in the lagoon will be all good. There are some nearby beaches and the town of Port Antonio for some variety if you’re there for a longer stay.
It was built log by log without crazy equipment, and is owned and run by Jamaicans.
You can book one of the stunning treehouse rooms here.
We met the manager, Timothy, who came to eat with us. I’m actually pretty sure he got the chef to take some food meant for our plates and put it on his… but no matter. He also gave us a bottle of wine so, fair trade. Timothy is very charming and an interesting character to say the least. He told us all about cricket, and I mean all. I feel like I could play the sport professionally with all the details he went on about. He also mentioned how Jamaicans don’t care about celebrities – but we still heard a lot about Beyoncé and Jay Z staying in one of the tree houses, his time playing soccer with his good friend Ussain Bolt, and how much he didn’t care about Sean Paul or his success.
Just outside of Kingston
This one looked and felt more like an Italian countryside villa. Hardly what you picture when you think of Jamaica, but it was fab! The house is owned by Chris Blackwell, who founded Island Records, which is pretty cool.
We had one staff member, Carleen, who was lovely and an amazing cook. I think the best jerk chicken we had (and we had a lot) was the one she cooked for us! The pool was a nice place to cool off and Jack’s Hill is relatively close to Dub Club, which I would call a must-do when in Kingston. Especially if you’re a reggae fan or music lover in general.
You can book the villa here on VRBO. I still recommend it… BUT if you’re on a tight budget this won’t be for you. We were hit with some surprise fees which left a bit of a bad taste in our mouths. Read below for details.
The final cost of your villa won’t be the price you saw online.
At the Jack’s Hill villa we paid a fee for the house keeper to get groceries, a fee for her to cook dinner, and a steep fee per night for every extra person after 2 guests (in a house that sleeps 9). None of that was clearly laid out on the VRBO page. If it had been communicated, we would have considered picking up our own groceries or even possibly cooking for ourselves. Though we would have lost out on that epic jerk. I’m happy to support the locals but the price was essentially double what we expected. Yikes!
The Silver Sands villa had three staff members and their work was included in the price, which makes sense to me. In both cases you’re expected to tip about 15% on the cost of your total stay so it adds up really quickly.
In my opinion, villas are still infinitely better than resorts, but they’re definitely not “all inclusive”. My advice is to organize a flat rate or get an estimate for the total (without tip*) so you’re adequately prepared.
*If you ask for a rate including tip it may show up on the bill and then you can’t be sure it’s going directly to the staff who’ve taken such good care of you! OR on the other spectrum, if they’re awful, you’ll be stuck tipping them what you originally agreed upon. Keep that cost separate and save it for the end of your stay.
At first, it felt a little weird having staff in the house, but I got used to it. We loved getting to know the people at our villas, and it’s nice not to have to cook, wash any dishes, or take out the trash like you often do when you stay in an Airbnb!
Sometimes Willy would sit down with us at breakfast to tell us about Jamaican culture or suggest stuff for us to do in the area. He hooked us up with a private snorkelling trip on his friend’s fishing boat, took us out to the local market to pick up some fruits we’ve never tried, and made us barracuda for dinner!
One night we were having some rum out on the patio, the boys were smoking cigars. Willy comes outside to chat and we get onto the topic of what previous visitors have been like. Do they get a lot of high maintenance people? What are your craziest stories? He starts to tell us about a woman who was very particular about each and every aspect of her trip.
“She would only eat vegan food. She brought a bunch of weird stuff with her. She brought this head…”
He paused, and motioned with both his hands like he was holding a ball. We sat in complete silence as we waited for the rest. My eyes widened, jaw dropped.
“What head?!” I finally screamed, waiting for him to tell me this lady brought a fucking shrunken head to Jamaica.
“This… this head of lettuce” he continued.
We burst into uncontrollable laughter, and he didn’t even stop the story. He couldn’t believe she brought her own lettuce. I sincerely believed he was about to tell us a tale about a human head in this house.
Areas of the Island
The vacation destinations you hear about most often are Montego Bay, Ocho Rios, and Negril. The draw is, of course, the beaches, but there’s lots of cool activities around too!
It’s on the western-most tip, and home to Rick’s Cafe, where cliff diving is a highlight. There’s also 7 mile beach, The Rockhouse Hotel if you’re looking for some luxury, and the epic Rabbit Hole at Reach Falls.
Montego Bay and Ocho Rios
They’re only about an hour’s drive from one another on the northern stretch of the island. The coolest activities ’round here include Dunn’s River Falls, Glistening Waters Lagoon, Martha Brae River Rafting, and the Blue Hole.
It’s known as one of Jamaica’s hidden gems, and hasn’t been built up like the other tourist hot spots. It’s a great vacation spot if you’re looking to get off the beaten track! This is where we stayed at Kanopi House, swam in the blue lagoon, and there’s also Navy Island and Folly Ruins if you’re interested in history.
Do you love coffee? Do you love hair pin turns and dirt roads only wide enough for one and a half cars? You’ll love the mountains! Check out Blue Mountain Bicycle Tours to haul yourself up a mountain in the blistering sun and get really sweaty on your vacation. Stop by Old Tavern Coffee Estate for the freshest cup of coffee you’ll ever have and an incredible view.
The capital city is home to the Bob Marley Museum, the epic reggae bar: Dub Club, some incredible ice cream spots, and Lime Cay if you haven’t had enough of the beach yet. Fleet Street boasts some amazing street art, but it’s in an area of the city that’s a little rough so don’t wander over on your own. In general, don’t go walking alone at night and keep an eye on your things. That’s the rule in virtually any capital city though, isn’t it?
While I didn’t make it to Negril or Ocho Rios, I made the mistake of going into Montego Bay for an afternoon. It was not cute. There’s a casino that attaches to a Margaritaville with a water slide in it. The prices are grossly inflated for absolutely everything. I was full of regret. It was even worse when we tried to leave.
We’re here on an unfortunate day that a cruise ship is in. Chesney and I just want to grab a taxi 10km out of this city to a restaurant to meet my parents. Seems easy enough. It’s a taxi ride, what could it cost, $10?
The first guy quotes us $80 USD and we walk away laughing. We then ask someone who works at a bar how much the drive should cost and she said $1. Umm what? Perhaps you’ve misunderstood. A 10km taxi. But yeah, she insists just 100JMD, or $1USD. I think maybe she’s talking about a local bus, but she says a bus or a taxi will cost the same. This makes literally no sense so we don’t get our hopes up that we can pull off a $1 taxi ride 10km away.
We ask multiple other cars and keep hearing 80, 60, and no one is budging on the price. We end up getting a ride for $20 which is probably the best we could have hoped for, but even that seems exorbitantly expensive. I think we’re getting a swindled because cruise ship tourists will pay whatever they’re quoted, $80 or otherwise. We confirm our suspicions with our driver who takes us for $20 – he says cruise ship visitors pay more.
All the more reason to get tips from your villa hosts… and to spend your time outside city centres like Montego Bay.