An English Countryside Cottage in the Caribbean

If you are a reader of this newsletter, you know that my love and affection for Round Hill, Jamaica is well documented, but I have fallen in love all over again at the discovery of this cozy and charming cottage, Almond Hill.

My family has rented villas in or near Round Hill over the years, but for this particular trip, there were only five of us going (my husband, twin boys and my mom came with us for a few days as well) so we did not need a big house but we wanted the amenities of a villa. I stumbled upon this charming cottage and it ended up being perfect for our needs.

Almond Hill has four bedrooms, with the possibility of only renting three for a lower price, and sleeps up to eight. It is one of the smallest villas I have come across in this area of Jamaica – most of them are on the larger side, with 5-6 bedrooms sleeping 12 or more – which you don’t always need.

The owners of the cottage are Guy and Lady Rose Monson – and I do not mean to stereotype but their names alone might give you an indication of why this Caribbean villa has all the charm of what I imagine a cottage in the English countryside might have. (Also I believe this is just one of their properties at Round Hill and in fact I think the entire Round Hill estate was owned by the family at one time.)

A few clues about the owner’s heritage if the names didn’t give it away would be the worn needlepoint topped card table complete with a well worn deck of cards, a silver monogrammed ice bucket in the bookshelves, black and white photos of the family members at various equestrian events, and books by British authors lining the bookshelves (I think my mother read three of them during her stay.)

What I loved about it most was that it clearly has not changed at all in 30 + years. I found an old scrapbook and there are photos from big parties at the cottage in years past — the same furniture in those photos is the furniture they have now, just with different fabric. It is classic, comfortable and I love that the owners do not have any desire to modernize it like many of the other villas in this area.


I know the check or not to check debate is raging right now given all the insanity with post covid travel, and I really could go either way on that decision with one exception: Villas in Jamaica.

And the reason is this: You will want for nothing when you rent a villa in Jamaica.

As I have mentioned, your meals are prepared, your rooms are cleaned daily, coffee is ready for you when you wake up and cocktails are made for you when you feel thirsty.

But most importantly for this decision, your laundry is done for you every single day and brought back to your room folded on a tray – which means that you only need a couple of pairs of pajamas and workout gear or tennis clothes, your kids only need a few swimsuits and t-shirts, shorts, a couple of nice outfits for dinner and that’s it. So there is truly no need to check if you stay in one of the villas that offers these services (not all do – you can email me if you want more background on the differences).

But what about the sunscreen you ask?? I had the same thought too and here’s the answer. Two options: 1 – ask the villa manager to purchase some for you in town when they are grocery shopping or 2 (this is the one I recommend) – buy plenty of these little bottles that meet the TSA liquid restrictions and you’re good to go.

Supergoop SPF 50 Mist – I love this Supergoop spray (and only 3 ounces). Works really well and not too sticky like some of the cheaper brands. Save those for the kids.

Unseen Sunscreen SPF 40 and Glow Stick SPF 50

Mineral Spray SPF 50 and Glow Oil SPF 50

Coppertone Sport Sunscreen SPF 50 – $2.99 – order these 1.6 ounce sunscreen cans in bulk and throw them in your suitcase.

And reminder that you need this travel bag to place on top of your roller – it holds so much stuff. The bottom section unzips and you can fit all your shoes and books (and sunscreen bottles!)

I have written a lot about Jamaica and my thoughts on renting villas – if you want more details go to the Travel section on my website, click on Jamaica and you will find all my posts and advice there. Or you can click here.

One love!

Private Pool
Who I can only imagine are Guy and Lady Rose
Fresh fruit every morning
Breakfast cart. I am not even sure if you could buy one of these anymore.
Coffee prepared each morning and ready for you when you wake up. Again, not fancy – no lattés or cappuccinos here – but the Blue Mountain Jamaican coffee is delicious.
How adorable is this little cup and saucer?
The china and tablescape changes daily with each meal.
Chef Tracey who made us the most delicious meals including breakfast, lunch and dinner
Eclectic mix of cookbooks in the kitchen.
Even the books are worn but still somehow perfect.
The villa has a great sound system; we played music every night over cocktails and dinner.
All the supplies you need for a week at Almond Hill: Sunscreen, Bugspray, and a deck of cards
Fresh flowers all over the house.
The original British/Jamaican connection — Ian Fleming, author of the James Bond novels.
A weathered needlepoint card table
The main room is so comfortable.
The prettiest details such as these doors throughout the cottage.
We spent most of our time here on this verandah – coffee in the morning, sunset cocktails at night, reading books on rainy afternoons.
The villa concierge will stock the bar with anything your heart desires prior to your arrival. As you can see, we chose Doritos, chocolate chip cookies and rum punch but you may not be as fancy as we are, wink wink.
Cocktail hour = rum punch.
Feelin fine.
You can either have dinner at the house or down at Round Hill. We like to alternate throughout the week – one night at home, one night out. It depends on what is going on at Round Hill – our boys love Jamaica Night. Pictures below.
The dinners at home were pretty special.
To further the English Countryside motif, the owners have two beautiful dogs that “live” at the house. You can request that they not be there during your stay if you have an allergy, etc., but they are so sweet and not bothersome in the slightest.
My boys loved spending time with the dogs
Another option for dinner venue
One of the master bedrooms
Master Bath
This one had an outdoor shower.
Another master bedroom.
A seahorse chair…💙
The master bedrooms open out to the lawn.
Bedroom with twin beds where my boys slept.
Spending time at Round Hill. They closed the tiki bars post-covid for a long while but they are back open now and it is my favorite place to have lunch. We are Team Larry’s bar for lunch and head over to Stanley’s for cocktails later in the afternoon.
My daily lunch – tuna niçoise with a Red Stripe Light.
The most gorgeous infinity pool anywhere.
Walking into dinner at Round HIll
Jamaica Night!
We played tennis every day.
This photo album/scrapbook was in the living room and it was so much fun looking through it and seeing all the memories this family has enjoyed at Almond Hill over the years.
Inside the scrapbook – this is a poem someone wrote in honor of the owners’ history at Round Hill – if you read the poem, apparently it had something to do with a flight being diverted to Jamaica.
There are lots of pictures of a milestone birthday or anniversary party that looks like it was a ton of fun. As you can see, this guest dressed up like a Red Stripe beer – ha!
Cheeky artwork of a “puffer fish” in the bathroom.
Hanging out during tea time.
My favorite photo in the Round Hill Bar on the very best dance floor.
Almond Hill was wonderful – we have already booked again for next year.

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