Caribbean Queen: A Peak Inside Cottage 8 + Tropical NYE Dresses & Accessories

Cottage 8 at Round Hill, Jamaica

A couple of years ago on my second cancelled trip to Tuscany, I had a decision to make:

Where should I take my group of 13 people to make up for the cancelled trip to Italy?

I needed a big house with lots of bedrooms, activities for the kids, the ability to outsource meals, and entertainment for everyone. After mulling this over for weeks (months?), my husband gave me the good advice to stop overthinking it and pick a place that I know and love and that meets all the requirements: Round Hill, Jamaica.

Because it was a mid-summer trip, we were able to take advantage of off season rates and perks and upon the advice of the resort regarding the make up of our group, we ended up renting Cottage 8.

There are approximately 30 villas spread throughout the Round Hill property as well as a small Ralph Lauren-designed boutique hotel. I love the hotel as much as I love the villas – the villas are larger and you have the option to have your meals there which is nice, but the hotel is also gorgeous and very close to the pool and beach.

We all loved staying in Cottage 8 – it is right by the tennis courts and an easy walk down to the beach, pool and restaurants. There are four bedrooms in the main house and a spare bedroom and bathroom with an adjoining porch a short walk up from the main house. The villa has its own pool, kitchen, den and multiple areas to gather on the patio.

Here are a few snaps of the villa and our stay. Jamaica is top of mind for me right now since I am headed there after Christmas with my family. I look forward to ringing in the new year in paradise – now the only question is, what to wear?

Tropical inspiration below. 🌴

And PSA: Sincerest apologies to those who will have the Billy Ocean song on a constant loop in your head for the next two weeks now that you’ve read this…Happy New Year.

Another PSA: The taxi ride from the airport to the resort is a two beer trip.
This is the view from the back of the house overlooking the lawn – the bedrooms all have their own entryway. There are four bedrooms in this building and one separate bedroom/bathroom just a few steps away.
Lots of great seating areas to hang out.
Round Hill has the best sunsets.
This is the den – those large doors close so you can have air conditioning.
This is the view from the lawn looking up to the house. The kids played football and hide and seek out here.
One of the Master Bedrooms. They all had Kings except for one with twins and they brought in one more set of twins for the kids at no charge, which worked out great. And sorry these photos are so dark; I did not take very good pictures on this trip.
This is the bedroom with the twins. They have their own entrance — a bonus because the boys could wake up and go hang out on the porch and not wake anyone up.
All the bathrooms are dreamy.
Walkway to the spare bedroom suite.
This is the fifth bedroom up those stairs.
Seating area outside the fifth bedroom. I think they will rent this separately from the main house if a renter is only using four bedrooms.
My son loved to camp out here during rain showers.
I was so tempted to put this in my suitcase.
And this too.
Everyone gets these great canvas bags when you check in.
When you rent a villa you have HUGE breakfasts prepared for you each morning – eggs, fruit, pancakes, pastries, and lots and lots of bacon.
Another seating area where we spent a lot of time hanging out. This was our happy hour spot.
You can order one of the straw bags or other designs while you’re at Round Hill from Straw Boss Richard.
Card Sharks – nightly activity before dinner in the bar.
Somebody loves a martini; could care less about the cards.
The martini effects are settling in. We love a good selfie.
Had fun celebrating my birthday on our trip.
Todd/Toddy/Weiss of Life/T. Weiss – his phone and scotch are never too far away.
A Birthday Snorkel
More cards with my boys.
Best pool on earth.
Until next time, Round Hill – I am on my way!

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