Jet Set: Round Hill Hotel and Villas Jamaica

Ever since I returned from my visit to Bermuda last month, I have been wanting to go away for a long weekend getaway to a beach destination with Fabian. If we lived on the East Coast, Bermuda would be a no brainer since it’s a direct, two-hour flight there. However, it’s a little harder to get there from Texas, so travel time is a big consideration. I’ve looked into going to Cabo San Lucas or Playa del Carmen, but while both destinations are beautiful, we are going to San Miguel de Allende in Mexico in a few weeks. I loved the British influence and truly tropical feel in Bermuda, so I’d love that in a destination. Over the weekend, I started thinking about tropical destinations where we could spend a long, relaxing weekend and Round Hill in Jamaica came to mind. I’ve always associated Round Hill with the fact that Ralph Lauren has a beautiful home there, but the more I researched the destination this weekend, the more I came to love the idea of visiting.

Round Hill is steeped in history. The 100-acre peninsula was originally part of Lord Monson’s Round Hill estate– a sugarcane plantation which later grew coconuts and allspice. Eventually, Jamaica-born entrepreneur John Pringle sought to create a boutique hotel concept on the island that would allow for people to purchase villas on the property and share in the hotel’s profits. Famous guests from the Montego Bay resort’s heyday in the 1950s and 1960s include Errol Flynn and Ian Fleming, John F. Kennedy and Jacqueline Kennedy who famously honeymooned in Villa 10, as well as Alfred Hitchcock and Bing Crosby. “The original architecture was designed by William Ballard and the décor was conceived by Guy Roop. Collaborating with Mr. Pringle, they brought to fruition a collection of impeccably designed, freestanding, whitewashed cottages that capitalized on the incredible views of the bay and warm, Caribbean climate.” The cottage colony model that Pringle had devised for Round Hill at 26 years old has since been widely emulated all over the world. For the past sixty years, Round Hill has maintained its relaxed, secluded ambiance and charm, while many of the private villas have been remodeled and modernized. Most recently, the oceanfront rooms in the Pineapple House were redesigned by Ralph Lauren, whose own villa is located at Round Hill, whose influence can be found in his collections every now and again.

I would love to know if you’ve ever stayed at Round Hill and if you would recommend it? We really just want to go somewhere that is a short, direct flight from Houston, where we can relax for say, three days in chic, comfortable surroundings. All I want to do is go to the beach, catch up on my reading, and enjoy what the Italians call “il dolce far niente”, an expression which roughly translates to “the sweetness of doing nothing”. What are your thoughts? Is Round Hill as fabulous as it looks or would you recommend another destination?

{The Pool}

{The Spa at Round Hill}

{The Beach}

{A Tropical Moment}

{One of the 36 Guestrooms in the Pineapple House which were Recently Redesigned by Ralph Lauren}

{A Bathroom in the Pineapple House}

{A Guestroom in the Pineapple House}

{Private Villa No. 7}

{Villa No. 7}

{Villa No. 11}

{Villa No. 16}

{Round Hill is also a Popular Destination for Discerning Brides}


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Tell Me What You Think! leave a comment...

  1. It looks gorgeous. You should go. I believe Jack and Jackie went to Acapulco on their honeymoon, however. Enjoy and have a margarita for me…

    1. Maybe the Kennedys took multiple honeymoons? I also thought they’d honeymooned at the San Ysidro Ranch in Santa Barbara, but the website for Round Hill says they honeymooned on their property.

      1. They could afford it, LOL. I’ve been a follower for years. Love your style and your blog. Hope you enjoy your getaway.

  2. I’ve stayed there for a friend’s big anniversary celebration. We were a large group, some staying in private villas and others at the Pineapple House. We had an amazing time and it was a perfect venue for the celebration. I enjoyed the Spa, hanging out on the beach, local shopping trips and it was just super relaxed yet beautifully comfortable. You would absolutely enjoy yourselves there, it has a fascinating history as well. Pack your bags!

  3. We absolutely love Round Hill. It has so much more charm than your typical high-end resorts. The only downside is the beach is a little cramped, but they have a wonderful adult only lawn with hammocks that leads into the water (lawn to water beats beach in my opinion). It has an old fashioned, storied vibe with beautiful design. The bar with black and white photos of guests in the 1950s and 60s is so fun. Small aside – they have the best childcare program of any hotel I have ever been to.

  4. Curtain Bluff in Antigua is amazing . Don’t think they suffered much hurricane damage at all. Not sure how direct that is for you from Houston? Never been to Round Hill.

  5. We honeymooned there in ’16 and it was truly idyllic. Depending on the time of year, they’ll likely upgrade you from the Pineapple House to a private villa at no additional cost. The service is first rate. We still keep in touch with Angela, our sweet cook. Be sure to see if they’ll allow you to see any of the private villa interiors…I know Meg Braff does a lot of work there worth seeing!

  6. Paloma, you will absolutely love San Miguel de Allende. Be sure to check out Casa Armida and Recreo while you are there. Lisa Coleman, who founded Recreo, is an SMU grad and makes gorgeous caftans, wraps, and kimonos. Would love to see a post on her! Love your blog, as always, and looking forward to hearing about your trip!

  7. My husband & I stayed in a villa at Round Hill a few years ago and it was lovely. The surrounding area, however, was not. Of all the recent vacations we’ve gone on, my most favorite place is TULUM. Have you been?

  8. You should go. It’s amazing. My husband and I went a few years back and loved the views and the villa we stayed in. I agree with the comment about the surrounding area, and the beach area is relatively small.

  9. Paloma, I’m so excited for your trip to san miguel and hope to hear about it after! we almost got married there but opted for oaxaca instead. unless you’d rather not go to mexico twice in short order, going to the beach will be such a different experience than landlocked (and 6,000 feet above sea level) san miguel. no one has mentioned los cabos – also a 2.5 hour flight from houston. but if you want to get in the water, it’s crashing cold pacific, not our gentle, bathtub warm gulf. i definitely do not recommend costa rica – we were lured by friends from nyc who insisted their travel agent said it was the most expedient destination for all of us. the agent failed to mention everything is at least two hours from the airport so between international two-hour advance check in at the airport, flight and drive time we lost nearly a day each way. would you consider shortening the entire trip by taking a domestic flight? we really enjoy both la jolla (20 minutes from san diego) and manhattan beach (15 minutes from lax) for weekend getaways like you want. and there’s zero brainpower required since the culture is so familiar – we find those weekends really restorative. i know you’ll love whatever you end up doing – just don’t think too hard about it or that will start to make it feel like work instead of play.

    1. Kate, this is such fabulous feedback. Thank you so much! It’s funny you should mention Cabo, because it Round Hill doesn’t pan out, Cabo is my other option, but seeing that hurricane season is upon us, California might be the safest bet.

  10. We have stayed here over 7 times withand without kids. We live in so Cal so we must love a place to travel as long as it takesus to get to europe! We’ve stayed in the lovely hotel rooms -sweetly nicknamed”the barracks “ and in villas. AlL arE fun and worthwhile. Most staff has been there forever and become friends. Joseph the gm runs a tight ship. Wverything held to high standards. Liaten if im laying on the swim platform with ricki lauren and ralph is reading the paper on the beach it cant be that bad. Some new activity every night. Loads of tradItionwhich we love and when we go ourselves we dont leave property. Yes, everyone ahould fo tHere once in a liferime if possible. Spa is amazing. The soundof the waves on the rocks on the way over is my happy place i go to when i get shots aT the dr office😎 fo and wnjoy and say hi to atewart the barTender and have a yellowbird. Yummy! Give us a Report!

  11. My husband and I spent a long weekend at Round Hill For my February bday a few years ago. It was absolutely beautiful and very charming. We were lazy and mainly lounged by the pool and beach. The food was delicious. The downside…unlike Bermuda (been there too), it’s not advisable to explore on your own on a moped. We had dinner off the property one of the nights; had an equally delicious meal at a nearby locals place. Junior was our driver…very nice gentleman!

    1. Hi Lisa! I have heard that about Bermuda vs. most of the CARIBBEAN. I do worry about safety, but if we go, we will definitely just stay on the resort. Normally, we love to explore, try various restaurants, etc. but given th safety issues and the fact that we just want to unplug and relax, i don’t think we would leave the property, which will be a first for us!