Flower Hill: An Ideal Villa for Multi-Generational Groups

I have had the privilege of staying at some fabulous vacation villas, and Flower Hill might be at the top of my list of favorites.  Flower Hill is an amazing 9-bedroom villa in Montego Bay, Jamaica.  It overlooks the Half Moon resort but is in a private, gated community.  Not only is the house beautiful but it is also superbly conducive to a multi-generational holiday.

Flower Hill Villa Jamaica
The spectacular Flower Hill villa as you approach from the driveway

The House

One of my criteria for a fabulous villa for intergenerational vacations (or large groups) is that everyone has sufficient space to escape and enjoy their privacy, while still having wonderful common areas to gather.  Flower Hill has both.   With over 19,000 (!) square feet of house, there is plenty of space for hiding away when needed.   There are 9 bedrooms, 3 of which are attached to one of the other suites, making them best-suited to families with children.  All of the bedrooms have their own bathroom.  There are four master-quality suites, making it easier if multiple families are splitting the bill.   Every room also has its own television with plenty of international channels.

The upper level master-suite at Flower Hill Villa in Jamaica
The upper level master-suite at Flower Hill Villa in Jamaica

Making the house feel even bigger are the huge patios and balconies that encircle the villa.  These fully furnished outdoor areas feel like an extension of the house.   With this setup, every bedroom has direct access to a balcony or patio, and almost all of the rooms have an outdoor sitting area that feels private. The common areas in Flower Hill are some of the most outstanding I’ve seen.  In fact, the upstairs Hemingway Room may be the coolest room ever.   It is located in the center of the house on the second floor and covers the full width of the house.    The walls are designed to be pushed back so that both sides are completely open to the lovely balconies and provide exquisite views.  The room has a pool table, a full bar, big screen TV, and plenty of seating.   It is an  absolutely fabulous place in which to hang out.

Playing pool in the Hemingway Room at Flower Hill
Playing pool in the Hemingway Room at Flower Hill

If, however, that area doesn’t suit you, there is the common area on the main floor looking out on the pool.  Here there is plenty of comfortable seating, another bar, and both indoor and outdoor dining rooms. But the common areas continued to the lower level where there is a huge game room equipped with a ping pong table, shuffleboard table, foosball table, old-school PacMan video game (no quarters needed), big screen TV, Netflix, DVD collection, and cupboards of board games.   My extended family had a great time and lots of friendly competition down here.  (I can easily imagine this being a favorite escape for teenagers.) Also inside the house you will find a large and fully equipped private gym, separate spa area, sauna, and a small office.  There is, of course,  a large kitchen, but as the house comes fully staffed, guests won’t be spending time in there.

Gym Flower Hill luxury villa Jamaica
The private gym

The house also has an elevator.  While this may seem unnecessary, it makes Flower Hill ideal for those with mobility issues and does come in handy for moving suitcases.  This is one more reason I love this villa for multi-generational holidays.

The pool and outdoor areas

Flower Hill’s outdoor areas are just as lovely and luxurious as the interior.  The centerpiece is certainly the huge infinity pool.   The 30’ x 55’ heated pool has a jetted hot tub on one side and a still-water cooling tub on the other.  The main pool has a resistance jet that can be turned on for anyone looking to do more than just float and splash in the pool.   The upper level infinity pool cascades down into a crescent shaped splash pool below. The pool is fabulous for all ages.  There are two large platforms with only a few inches of water.  While designed to contain lovely lounge chairs and umbrellas, they also create ideal splashing areas for babies and toddlers.   They are also pretty ideal for enjoying a cocktail or just putting your feet up.  While not zero-entry, these shallow areas are also good for those with limited mobility to access the pool more easily. Next to the pool is an outdoor bar as well.

Flower Hill pool view luxury villa
The view from Flower Hill

With a name like Flower Hill, you might be imagining a villa on a hill surrounded by beautiful gardens.  Which is exactly what Flower Hill has.  The grounds are large, and while sloping, have flat areas for playing croquet or bocce and a volleyball/badminton court.   There are also great circular lounges and a relaxing swing.  Flower Hill has more than enough space for energetic kids to run around (both indoors and out).   The outdoor space is almost tiered, and on the lower level there is a barbeque and firepit, as well as a picnic area.  The staff set up a very festive outdoor dinner for us one night, complete with fairy lights and s’mores.

Flower Hill BBQ dining
The lower lawn at Flower Hill set up for a festive Jamaican-themed BBQ

All of the outdoor areas are wonderfully lush and landscaped and well maintained  by the staff of three gardeners.


Speaking of staff, Flower Hill has an amazing team that makes sure you don’t have to lift a finger.  There is a core set that works full time, plus additional staffers that are brought in with larger groups.  For our group of 18 there was a staff of 13, including the three gardeners.  Nothing was too much for them.

Butler Preparing drinks at Flower Hill Grand Family Getaways
Our butler preparing our favorite cocktails

The staff clearly take a great deal of pride in their work.  The laundry is returned to you with flowers on top of each basket.  Beds are turned down at night.    I even learned a new term while visiting Flower Hill, “scaping”, as in creating themed table-scapes for the main dining table each day.  That’s right.   Every day, if not every meal, featured a different set of table linens and centerpieces.   Flower Hill even has a “scaping room” just for storing all of the accessories that make each meal a unique experience.

Flower Hill villa Jamaica Grand Family Getaways
Just one of the many impressive tablescapes the staff created every day


While you could happily never leave Flower Hill for the duration of your vacation, there are plenty of things to do nearby. The house overlooks the Half Moon golf course, and as guests of Flower Hill, you have access to the resort amenities of Half Moon.  This includes unlimited free green fees at the Half Moon golf course, access to tennis, fitness center, croquet, and the beach and watersports.  It is a 5-minute drive down to the resort and you also get a discount on many lessons and golf cart rental. In addition to the Half Moon golf course, Flower Hill is within a short drive of the world-renowned White Witch and Cinnamon Hill courses. Montego Bay is only a 15-minute drive away, with all the nightlife, restaurants, and shopping that the city offers.   Very close to the villa is a zip-lining center that offered great fun and adventure for our family.  Almost everyone in our party went zip-lining and loved it, including my 6-year old nephew and 70+ father-in-law. Our driver also took a group of us to his favorite local “jerk” place, Scotchies, which was awesome.  A highly recommended stop for lunch.  

Great for Everyone

There is something for everyone at Flower Hill.  I honestly can’t think of anyone I wouldn’t recommend the villa to… families with babies, teenagers, young adults, seniors.  Not only is the villa extremely well-suited for large groups, but the amazing pool and proximity to a range of activities make it great for everyone from babies to seniors.  It is ideal for multi-generational getaways. We booked Flower Hill through Villas by Linda Smith, who along with her team, provided excellent service.  During low season, 1-5 bedrooms can be rented for $20,000/week.  Rates are higher for additional bedrooms and in high season.

Flower Hill 7 bedroom villa Jamaica Grand Family Getaways luxury vacation rental
The expansive upper balcony at Flower Hill


Garden flower hill luxury villa jamaica
Places to lounge in the garden of Flower Hill


Flower Hill mult generational vacation villa Grand Family Getaways
The palm-lined driveway and front gates


Flower Hill Villa Grand Family Getaways
Flower Hill at night


Flower Hill pool Montego Bay Grand Family Getaways luxury family vacation
Flower Hill pool lit up at night


Flower Hill 7 bedroom villa Jamaica Grand Family Getaways luxury vacation rental
The expansive upper balcony at Flower Hill


Cocktails Flower Hill butler
Cocktails at Flower Hill


Pool at Flower HIll Villa Grand Family Getaways
A view of the pool and back patios at Flower Hill


Flower Hill villa pool
Flower Hill pool at dusk


Croquet flower hill jamaica
Playing croquet at Flower Hill


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