Mountainside Guesthouse with stunning coastline views Reviews, Deals & Photos 2025

Q: Does Mountainside Guesthouse with stunning coastline views have a pool?

Yes, this property has an outdoor pool.

Q: Is Mountainside Guesthouse with stunning coastline views pet-friendly?

No, pets are not allowed at this property.

Q: Where is Mountainside Guesthouse with stunning coastline views located?

Situated by the sea, this guesthouse is within 6 miles (10 km) of Boston Bay Beach, Jamaica Beaches and Long Bay Beach. Winnifred Beach and Blue Lagoon are also within 6 miles (10 km).

10/10 Excellent

Anna H.

7 Mar 2024

Absolutely beautiful

The property is very nice and taken care of. They view from our balcony is absolutely breathtaking. Amazing food and beach within walking distance. John was super helpful and gave us advice as of where to go. He really cares. I will be back.

Stayed 5 nights in Mar 2024

10/10 Excellent

Astrid & Mathias B.

11 Apr 2023

One of a kind

Stunning location with breathtaking views. Our suite featured everything we needed, best thing is the hammock on the balcony. If you don't feel like driving down the hill to the beach, just relax in the pool with a view of the whole valley. John went out of his way to make our stay memorable - and it was! Thanks

Stayed 6 nights in Mar 2023

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Sarah A.

17 Jan 2009

My Favorite Place In The World

I can't even find the right words to express how wonderful it is to stay here. The view is unlike anything i have ever seen. The rooms are so big and spacious. The hammock is a perfect touch. Dread is the BEST cook , NO QUESTION! The dogs are so sweet. I love the town and the people. I have stayed in this town nine times and have felt nothing but warmth and kindness EVERY time.

This review was submitted before 2018 and has not been verified.

8/10 Good

Laura O.

22 Jun 2013

Caribbean Dawn--Stunning!

The Caribbean Dawn was a wonderful small hotel structure in an amazing setting. The views really are beyond belief, with a balcony w/hammock and chairs to look down on the green lush vegetation, the beautiful sea and shoreline, and to watch the sky, sunrise and weather passing through--all protected on the covered deck. The setting is high up from the coast, so be prepared to do some hiking, have your own vehicle or catch a taxi up to the top. The manager Jason is very accommodating and helpful. The beaches in this NE part of Jamaica are the best on the Island.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Victor C., Miami, Florida

24 Aug 2016

Beautiful Views and Excellent Service

My fiance and stayed at this property for 3 nights and we were blown away by the amazing view the property had! We were greeted by Jason, who was very friendly and helpful throughout our entire stay. He recommended beautiful beaches, delicious food spots and fun activities for us to do. He accompanied us to Reach Falls and made sure we received wonderful treatment. We enjoyed the pool which was very clean and also had an amazing view. I highly recommend this property to anyone staying in Boston Bay! THANK YOU

This review was submitted before 2018 and has not been verified.

10/10 Excellent

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9 Dec 2012

Best Family Vacation Ever

This trip to Jamaica was my son and I's first trip out of the country. It was an incredible experience. The location is perfect nestled on the top of a small hill that exposes all the wonderful views of the ocean, Boston Bay and all the action in the local community. Just minutes from the cove that is Boston Bay that includes a beautiful beach with local shops and great Jamaican food. The hotel is very well maintained with great friendly people. Every room has a view to die for. Also the rooftop views make you feel like you are on top of the world. Great Job! Everything was perfect.

8/10 Good

Anil B.

26 Jan 2023

Harmony Heights

In it itself my stay was a bit of an adventure and it is important to remember just how exactly to get back up the hill after leaving the property. The hills are steep and not recommend for those who lack strength and stamina. I wouldn’t recommend the property for anyone who isn’t physically fit. The property owner was very approachable and level headed. The pool was clean and well regulated. The WiFi worked as intended. If you are an avid photographer the views taken from above Port Antonio were phenomenal. I think I might revisit in the near future as this place is a hidden gem.

Stayed 3 nights in Jan 2023

This review was submitted before 2018 and has not been verified.

10/10 Excellent

MArie B.

21 Apr 2015

super getaway

My partner and I had an amazing time at this wonderful place. the brown room is huge, a nice little kitchen and a beautiful balcony. This place was a great therapy for my partner whos scared of heights ;). beautiful view. the hill is quite chalenging and I decide to walk up with all my luggages. not a good idea...take a cab. This EGO decision wasnt to clever ;). But without luggage, we would go up and down the hill everyday without any problems. Be carefull with the dogs from the neigbhourg that already bite some guests and almos bite me too. THAT WAS SO SCARY. The neighbourgh was looking at the scene and didnt do nothing to help me. I was happy to be my partner who knows how to deal with crazy jamaican dogs. but , as you can see those dogs didnt take a star of the rate. Someone was there to welcome us and is very friendly. thank you very much and we will come back soon

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Leila T.

12 Dec 2012

You'll never want to leave

My trip to Boston Bay was one of the most amazing vacations I've ever had. The place itself is unlike any other Caribbean town I've been too. You'll certainly run into tourists there, but relatively less than places like Montego Bay or Negril. The residents of the town are friendly unlike anywhere I've been before. They are not simply interested in talking to foreigners to scavenger for money, instead, they have a genuine interest in making sure you have a good time! My days usually began at 6am, with a view of the sunrise from my balcony. I liked to think that I got the good room, but the truth is, every room has a breathtaking view. It is about a 20 minute walk to the beach, but it's all down hill, and it is very relaxing and quite easy if done before the hot late morning/afternoon sun. I'd spend hours at Boston Bay beach, where you can get surf lessons from the locals, go for an adventurous leap of the cliff, or simply bask in the wam Jamaican sun. When you get hungry, you can take a short stroll to the Jerk Centre, where they'll jerk just about anything you ask them to (including sweet potato for you veggie-heads!) and accompany it with festival (a kind of corn-bread churro if you will). You can also get very decently priced food at the beach if you're in the mood for something less spicy. When you're spent from the beach, you can head back to Caribbean Dawn in a taxi, which will take up hill for about 400 Jamaican dollars, and enjoy a home-cooked meal by Robert, the chef-in-residence at the B&B. He really is the handy-man and travel guide all-in-one, but his food is DEFINITELY something to write home about, and I guarantee you'll be missing it. For a late night, you could make a trip to any of the local bars for great reggae music and company. There was almost always something to do in the evenings whether it was a fish fry (which was actually a bunch of the locals eating stewed fish and playing dominoes), the weekly talent show (the most talent I've seen in one place, from rappers, to musicians, to dancers), or the road block party in Port Antonio (hands down one of the best parties I've been to, ever). I'm a young traveler, and I would definitely recommend Caribbean Dawn to 20-somethings who like chill vibes and could have the accessibility of clubs at their disposable, but don't need to be surrounded by the noise. I also recommend Caribbean Dawn to visitors looking for a view unlike any other, really everyone and anyone.

This review was submitted before 2018 and has not been verified.

6/10 Okay

BE L.

16 Jun 2015

Pros and Cons to this rental

I stayed for almost 2 weeks...maybe a week too long! Finding the property took a little doing, needs a better sign..pointing to the hill and where to turn once up the hill. We had to call several times to find our way. The hill was quite steep and rugged, I was concerned about the cars undercarriage. I stayed in the brown room which had a makeshift kitchen with a gas 2 burner cooktop, and a double sink in the bathroom next to it. There is a large refrigerator which is present in all the rooms. The room was large with a large, high comfortable bed with mosquito netting...much needed. There is a small balcony, equipped with a hammock, overlooking Boston jerk stand...eye level with the hawks The Caribbean sea is spread out before you and you can see the sunrise every morning! A really beautiful view, there is a plethora of stars at night! There is an infinity pool which is wonderful to splash in when the weather is nice! It was a little too cold during my stay to take much advantage of. The price is right including extra days thrown in. Now for my cons.... Internet is intermittant due to the altitude. Even purchased internet did not always work, so I wouldn't hold that against the owner. The balcony and rooms are not private...conversations are easily overheard. The dogs are unruly and a little frightening., They growl /bark at you, even at their caretakers, when not sleeping. But they are up all night barking. Jamaicans do not let their dogs in the house so all the dogs are out..what a racket! My last complaint was getting up and down that hill. It is not walkable, even for an ablebodied person! The young people staying next door were not able to navigate down the hill. You have to have a taxi (5$ each way) pick you up. The car on the premises is not always available or working. I kind of felt like a prisoner! The caretaker did check on you everyday if you needed anything. So I have mixed feelings about this property...the price is right and location is good but I would not stay there again but it may be good for someone with access to transportation.

This review was submitted before 2018 and has not been verified.

2/10 Terrible

Rick V., Fairhaven, Massachusetts USA

24 Jan 2015

WILL NOT RETURN!

Caribbean Dawn has so much potential but lacks in daily maintenance, administration, set policies and/or procedures for both guests and Property Manager. It is so lacking that we were forced to cut short our recent stay and will not return. The view at Caribbean Dawn and the morning sunrise is breathtaking and a God given gift. However, for my party of five, who rented 2 rooms (green and brown rooms), a decision was made to cut short our stay and relocate to a place that was better managed. After having stayed at Caribbean Dawn on two previous times this decision was not taken lightly. Our decision was based on several reasons but seemed to focus primarily on a lack of honesty with not only the owner but also with the property manager. Also after only 1 1/2 days of use the sink/basin in our brown room (bunk room) became clogged. We did not use the sink on our first and second day as we ate out. Since this was the room we cooked and all gathered in, most of our functions were greatly impeded. Management failed to fix the problem, offer any alternatives, (i.e. room change, or even a refund and/or compensation of any type. In fact as of the writing of this review no communication has been received from the owner or his agent relative to this problem. No apology has been communicated as of this time. Having taking a picture of the existing plumping of the kitchen sink in the brown room one can see that the plumping was not done properly. There are no clean out elbows, or sections that are threaded for easy clean out when blocked. The entire system is glued and needs to be disassembled, unblocked, and be professionally redone. If not blockage will continue to occur. Halfway through our stay we requested our towels be changed as they were wet, stinky, and simply needed to be changed. At this point we were told that policy was that for a small fee, $5.00, U.S., they could be changed. This was a policy that was NEVER told to me/us by owner nor property manager. This policy was not listed on any Caribbean Dawn website when I booked our stay, as I have the original website copied and saved. However the policy did appear on their website after I voiced our need to have the towels changed. This policy appeared late in the night on December 31, 2014, and was not previously listed. The property manager admitted this fact to me in a conversation we had on our departure day. Had I known about the change of towel policy I would have taken action on my ow

4/10 Poor

Brenda S.

1 Aug 2019

Disliked: Location, listing accuracy

Ridiculous driveway

This property is up a very steep switchback hill and then you go down a Cliffside driveway where you then have to get turned around to leave. I don't know if we would have made it out of there if we hadn't had a clearance 4 wheel drive vehicle. The manager kindly went out and picked up dinner for us and we had some breakfast food with us as we didn't want to do that trip more than once. We had booked and paid for three nights and cut our losses and left after one.

Stayed 3 nights in Jul 2019

2/10 Terrible

Verified traveller

31 Dec 2018

Liked: Cleanliness

Disliked: Amenities

Long drive up a bumpy narrow road to a dirty bed and pool. Greeted by 3/4 dogs biting at my ankles. No one came to greet me even though the dogs were barking. Bed smells really bad even after airing out the room for 2 hours.

Stayed 4 nights in Dec 2018

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Bastien C.

2 Nov 2017

Amazing stay at John's place!

From up Boston's hill, gorgeous view with roof pool, perfect place to chill and close to any Portland leisures, Apartments are recent, well equipped and Jason, manager of the place, runs the place perfectly, Strongly recommended!

Stayed 3 nights in Oct 2017

This review was submitted before 2018 and has not been verified.

6/10 Okay

Susan T.

9 Feb 2017

Oh wow spectacular views natural air conditioner.

The walk to and from the property had so many water views to enjoy. About 8 beautiful beaches to enjoy within 30 minutes from the property. Daily climb will give you all the daily exercise you will need. I cannot wait to revisit

This review was submitted before 2018 and has not been verified.

10/10 Excellent

A A.

3 Jan 2017

Nature, water, adventure

One of the best vacations by far!! This property is like your own villa at a guest house rate. Views, sights, and sounds of all of Jamaica's gems. Make sure to take the back trail from the house to the beach...and try the jerk sausage with festival. Huge thanks to Jason and his team for sharing the magic of Boston Bay! Can't wait for the next stay.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Anthony/Deidre h.

28 Mar 2016

Stunning Panoramic views

My husband and I had a short stay of two nights in the blue room. It was fantastic and too short of a stay. The room was clean, spacious, and had breathtaking views. The sheets smelled great and fresh, the towels also smelled fresh and were soo soft, the bed was comfy, and we appreciated the mosquito net over the bed. The pool area was extremely impressive! What craftmanship! It looks really great!! And what a killer view from the pool!! The view of the sunrise was amazing! Even the walk down the hill wasn't too bad. Along the way we spotted pimento trees, cinnamon trees, pear, ackee, and a June plum tree. Jason was great! Very down to earth and accomodating. His check ups on us were always timely and appreciated. Most times its impossible to improve on perfection, but I have a suggestion, perhaps a ping pong table and/or a dart board over by the picnic table. Overall, a fantastic stay that we would highly recommend to others. We will definitely be return customers.

This review was submitted before 2018 and has not been verified.

8/10 Good

Odette L.

27 Jan 2016

A wonderfull view!

Very well situate. Rooms are very clean well equip with a balcony face to the ocean. Bed very comfortable and clean. The owner John is very helpfull and answer to all your questions, so don't hesitate to ask.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Sarah A., NY

19 Apr 2015

you MUST stay here!!!

I haven't stayed at Caribbean Dawn for a number of years and I forgot what I was missing! The best part is the pool which is a new addition since my last stay. The view is incredible on it's own but it's somehow even more amazing while floating around the pool. I love how big the rooms are and the breezes will always keep you cool. I'm a huge animal lover so I was very happy to have the dogs to hangout with. They are super sweet with great personalities. My mom and I had a great time and I can't wait to go back.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Corey H.

1 Apr 2015

Can't wait to go back!

The place was absolutely gorgeous with some updates. This is the second year in a row my family (including two very young babies) and I have been there and its just the thing we need to escape our busy life in the states. Jason the grounds keeper was great and his hospitality was on point. Made us dinner on request and drove us around. Caribben dawn new pool was just perfect. Kids woke up went to the pool, ate breake fast, pool, beach, pool again and they were both out by 8pm wearing themselves out. Room was great, clean and the owner was there and actual built a rail for the bunk bed when saw that we had young kids and did it all before bed time. What s great place we found! We can't to go back next year.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

ellen D., Bellmore, New York

31 Mar 2015

Lush tropical views

We love staying at the Caribbean Dawn and have been coming for the past several years. Overall it is clean and well managed. Jason the manager took care of all our needs. We enjoy our morning coffee on the balcony, and this year enjoyed using the new pool. This is a welcome addition, we enjoy the beach at Boston Bay and the two new restaurants we went to this year. One was the Cliffhanger in Long Bay and the other was the Olde Marina in Port Antonio both were excellent. We look forward to our next visit. Frank and Ellen NY

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Kimberly L.

8 Dec 2014

a great and unexpected surprise

We were overwhelmed by everything...particularly the absolutely breathtaking view! It looks good on the pictures but even better in real and the pool is really impressive! When we arrived Jason, the manager, offered to pick up anything we needed and said that he would show us around town and bring us to good spots to keep us busy.. it was nice to have this personalized service, especially when you aren't sure what to do. It gets expensive being a tourist in Jamaica but Jason brought us to places that made us save money and we appreciated this. For now there is no hot water and I wasn't sure about this when we booked but it was okay after all and the owner John said that he plans on setting this up soon. There is good water pressure in the shower which is something most places we stayed in Jamaica were missing. The bed is comfortable.. we slept well. There is no A/C but we didn't feel that we needed it.. there was always a nice breeze. There is free Wi-Fi in the room, most places we stayed at in Jamaica only had it available in the lobby so this was great! We stayed for 2 nights and regret that we didn't stay longer.. There is so much to do around the Caribbean Dawn! We need to come back and we already said that if we did go back to Port Antonio we would stay here again.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Holdfast A.

20 Oct 2014

Great personalized travel experience

My husband and I just got back from a week at Caribbean Dawn near Boston Bay Beach outside of Port Antonio, Jamaica. It's a small guest house up on a hill that overlooks Boston Bay. There are only 4 rooms and we went in the off season, so for most of our stay we had the entire place to ourselves which was awesome. The rooms are simple but clean with high ceilings, a ceiling fan, windows on the balcony side, and vented openings up high on the opposite side to keep the air moving. We stayed in the Brown Room which has a small kitchen set up in the entry hall, a full sized refrigerator, and 4 seat table. We were a little nervous about not having air conditioning but it wasn't an issue. The breeze off of the ocean is enough to make the room comfortable for most of the day,and nice in the evening. It would start to get muggy around 11 but that is usually when we were leaving to go do something for the day anyway. The only time the bugs were an issue was around dusk if we were sitting on the balcony, but even then it wasn't bad, we just used some bug spray. I really don't think you can find a better value on the island. Caribbean Dawn seems to be a work in progress. Maybe that is why it is such a good deal? The pool is a newer edition, and while we were there they were in the process of building a restaurant on one of the upper levels that will have amazing views. Above that on the roof they are planning to build a gym. We took the option to have the car and driver for the week which was also a great value. For $50 US a day (plus the cost of gas) Jason, the manager will take you anywhere you want to go in his SUV. After paying a driver in Negril $200 to take my husband and I to some waterfalls on our last trip to Jamaica we really appreciated Jason taking us around. Both Jason and his assistant Kevin were really helpful showing us around, answering any questions we had and making recommendations. Jason even helped us do the math on the exchange rate our first day there, and arranged for Rob, a Kingston local who now lives in Boston Bay to drive us while we were in Kingston. Rob and Jason were really amazing helping us find some obscure spots in the city that we only had old addresses for. John the owner was great to deal with and helpful making reservations, setting up our airport pick up and trip into Kingston (all included in our 50 a day car service). You can tell he really cares about his place and the people who stay there. It

This review was submitted before 2018 and has not been verified.

10/10 Excellent

J D., NYC

9 Jul 2014

Stunning View,Warm Hospitality,the "Real" Jamaica

What do you need to know about Caribbean Dawn? - It is a 4-room guest house perched on a hill overlooking a seemingly endless expanse of lush countryside and the Caribbean Sea. Each room has its own balcony with its own version of CD's >180 degree view. - This view is STUNNING. I hike, snowboard, and travel a decent amount, but this tops every place I've stood or stayed in my entire life. See the pictures and let me assure you it is even better in person. As you sit on your balcony or by the pool, you are either eye-level with or looking down on the hawks gliding across. - It is hot at sea level but cool and breezy up on the hill - even if you like A/C on hot days, you won't miss it here. - The accommodations are simple but clean, bright, and comfortable - felt like "simple luxury" to me. You are "roughing it" only to extent you are enduring the crazy 2.5 hour drive from Kingston and tepid showers (I hear hot water is coming soon!). The "cold" water wasn't so bad - shower in the afternoon (after the sun has heated the water tank) and close your windows ahead of time to warm up the room. - You will contact John, the owner, to coordinate your stay and arrangements before you arrive. I actually just met him and he is every bit as cool and kind in-person as he is in making arrangements for your stay. I had many concerns and questions before my first visit to Jamaica and he was extremely responsive and detailed in his replies. - I am a petite white girl in my early 30s and traveled there alone, and I saw barely more than a handful of other tourists the entire time I was there (exactly what I wanted!). Jason, CD's house manager, met me at the airport and served as my personal host, tour guide, chef, and (quickly) friend for the duration of my 4 days there. He is a conscientious, gracious, and professional host who grew up in the area and knows how to take care of his guests. I wanted to see Portland, experience the "real" Jamaica, and get some surfing in, and he made it all happen in a long weekend. Even though Portland is a pretty poor area, I found its people to be kind and respectful, and I felt safe and comfortable the entire time I was there (thanks especially to CD and Jason). - I am not a "dog person," but the CD dogs were cool - they bark like crazy at unfamiliar visitors, but they never got in my face and generally minded their own business after our initial introduction. I'm already planning my next visit.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

ellen D., Bellmore, New York

18 May 2014

amazing views

We love the Caribbean Dawn, we have been visiting for the past seven years. We look forward to our yearly visit. Each year there are new improvements. We enjoy the view from the balcony, as we have our morning coffee. We love the beach at Boston Bay. We try new restaurants each year. The Jerk chicken at Boston is great. Jason is very helpful and provides us with our basic needs. Our favorite restaurant this year was Anna Bananas in Port Antonio. Can't wait to return next year. Frank and Ellen

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