When it comes to a winter break in those months when your throat is thick with Benylin for Chesty Coughs, anything with warm sea and palm trees meets with my approval. It was thus that we ended up on a family villa holiday in Jamaica. “The Caribbean?” we said. “We’ll go anywhere.”

Of course, not all Caribbean islands are equal, and some are more equal than others. Jamaica is very beautiful and tip-top as far as temperature is concerned, but is rather more politically complicated than other places. Gated resorts containing perfect ersatz tourist worlds are everywhere along the Jamaican coast. Our destination, the Tryall Club, near Montego Bay, emphasised the “comfort, privacy, security and convenience of a luxurious second-home colony”.

Villa holidays with a cook are absolutely the best thing for a family, far more flexible than a hotel. We landed up at Pineapple House, which had a small pool, a garden with green parrots flitting through the palm trees, and wonderful sea views. Unexpectedly large numbers of charming staff appeared at various times. Cleaning, laundry and cooking were all done for us, and a butler/waiter turned up in the evening to serve dinner, which was somewhat embarrassingly formal just for five — the villa usually sleeps eight.

The house had super- comfortable bedrooms (with panic buttons) and bright, pineapple-themed decor, which the children adored. The food was best when we asked for local specialities, such as shrimps, red beans and rice, and salt fish with ackee, a pear-shaped fruit. Otherwise the fare was aimed at the hefty American market, but there were great breakfasts of pancakes, French toast and piles of papaya, pineapple and watermelon.

The Tryall was started by Texans in the 1950s as a golf resort, but is expanding to be more family and celebrity friendly — Lennox Lewis has a vast pad on the hill here. Tryall has a fantastic free kids’ club, and while we played tennis, our children, aged 11, 9 and 6, learnt about the local wildlife (tropical birds, lizards and a mongoose), made tie-dyed T-shirts, and dug vast crenellated cities in the sand down at the beach.

Although I do not play golf as a matter of principle, the villa came with a golf buggy, since the resort is spread over a huge area of an old slave plantation, with an ancient water wheel still intact and running. So there we were, in our yellow golf buggy, racing past the ranks of palm trees, down a tunnel under the main road, to the beach side of the compound. “I know how Ronald and Nancy Reagan felt in their twilight years!” said my husband, foot flat on the accelerator as we topped 10mph.

After a few days in the resort, we ventured out into Montego Bay to see the museum, the site of the slave rebellion led by Sam Sharpe, and the old town. We were the only white tourists walking there, apart from a backpacker who slid uneasily from a bank guarded by a bouncer with a machinegun. The shops all had hefty security grilles. We knocked on the museum door, and a woman came out to tell us it was shut. The tiny slave jail in Sam Sharpe Square had been turned from a monument into a stall selling cigarettes and phone cards. We went shopping for T-shirts, but the badgering was hard going. Indeed, with kids, it was all a little bit edgy.

Most visitors stick to the tourist strip along the beach, dotted with international bars such as Jimmy Buffett’s Margaritaville. Few hire cars, relying instead on minibuses with drivers. In the taxi returning from Montego Bay, we saw police stopping schoolchildren in smart uniforms and searching their backpacks. For what? Drugs? We might have expected this in Kingston, but not on the touristy northwest coast.

Jamaica has a population of 2.5 million and tourism is its biggest earner, yet the dollar does not appear to be trickling down quite enough. (We felt we helped — the regulation tips for the villa staff were US$500, £290, for a week.) Yet the Jamaicans we talked to seemed to be hopeful about political change — the country’s first female prime minister, Portia Simpson Miller, took office in March, touting her “plan to reduce general lawlessness” .

Perhaps for good reasons, most of the tourist sights are carefully fenced in — you don’t go to see a waterfall. Instead there is the “Dunns River Falls experience”. You don’t visit the Martha Brae River. Instead a local guide has to punt you down it on a raft. We cancelled a “swimming with dolphins experience” after we realised it would cost £450 for five. We did love a kitschy night at the resort of reggae, limbo dancing and fire-eating, plus the Incredible Snake Man. Plenty of Bob Marley and UB40.

We also visited Rose Hall, a Gothic mansion on a former slave plantation, and were entertained with wildly inaccurate, gory stories about the mansion’s chatelaine, Annie Palmer, who supposedly did away with her three husbands. Her life is the subject of a Johnny Cash song, which our guide sang to us by her grave. The children loved the stories of how Annie “filled her husband’s ears with hot oil and his head exploded all over the toile de jouy wallpaper”.

However, the Gothic emphasis meant that visitors found out little about the history of slavery on the plantation.

I realised afterwards that our holiday was oddly coloured by reading To Kill A Mockingbird aloud to the kids over the week. The book is set in the racially divided American South in the 1930s, which made us all the more conscious of the racial and economic divide around us. To be honest, all that gated luxury makes me uneasy. A few years ago we stayed with friends who rented a villa, Sapodilla, in Tobago, which had a cook and cleaner. It was a much better experience. We felt comfortable jogging down dirt roads by the sea, driving ourselves to faraway beaches to eat fish cooked fresh by the locals, hanging out in bars and betting on the village goat races. Beyond its tourist compounds, Jamaica is not relaxing in the same way.

Need to know

Kate Muir stayed at Pineapple House, booked through A&K Villas (0845 0700618, www.abercrombiekent.co.uk), which sleeps up to eight people from £4,004 a week, including airport transfers. Air Jamaica (020-8570 7999, www.airjamaica.com) flies from Heathrow to Montego Bay from £590 return.

Reading: Jamaica (Rough Guides, £11.99).