The Rockhouse in Jamaica is 'the friendliest fashionable hotel I've ever known,' says Decca Aitkenhead. Photograph: Alamy
The Rockhouse, West End, NegrilIf you're after the cliff-edge drama of the West End, but don't fancy slumming it, the Rockhouse is probably for you. Some of the West End's most upmarket hotels are so antiseptic and uptight you'd hardly know you were in Jamaica, but the Rockhouse has managed to combine modern boutique comforts – a world-class spa, crisp bed linen, fabulous food – with the laid-back hedonism of the old Negril. The rooms look a bit like stone thatched wigwams, some with private terraces, but it's the drama of the cliff-edge dotted with diving platforms that holds everyone's attention, alternately tempting and terrifying. It is the friendliest fashionable hotel I've ever known.
• rockhousehotel.com, double rooms from $125 a night plus taxes
Palms Resort, NegrilA lot of the mid-range hotels along Negril's white sandy beach have seen better days, but the Palms' natural wood aesthetic has aged more successfully than the gaudy tropical motifs of its neighbours. From its stylish wooden decking and beach bar, just feet from the water's edge, you can enjoy all the spectacle and carnival of Negril's beach life, but the property itself is peaceful, and the service has all the efficiency of a much pricier hotel, with none of the formality. There's nothing phoney about the relaxed friendliness of the staff; by day two, the gardener was busy teaching my toddler to speak patois.
• thepalmsnegril.com, double rooms from $80 a night plus taxes
Banana Shout, West End, NegrilThe rocky stretch of Negril known as the West End became a mecca for hippies in the 1960s, and Banana Shout evokes the best of the old bohemian spirit, perched on the edge of the cliffs right next door to Rick's Cafe, the famous sunset diving spot. The four cottages have a lovely rustic charm, and the whole property has a friendly communal feel. Guests tend to be likeably left-field travellers rather than tourists, and Milo, the Italian owner, is a mischievously charismatic host. The cottages have little kitchens, but if you like, Milo will cook for you in the alfresco bar/kitchen, making Banana Shout feel more like a home than a hotel.
• bananashoutresort.com, double rooms from $80 a night B&B plus taxes
San San Tropez, Port Antonio, PortlandFrenchman's Cove. Photograph: AlamyToday's fashionable jetset like to winter in Barbados or St Barts, but half a century ago they flocked to the luxury villas and exclusive hotels just east of Port Antonio. The atmosphere these days is heavy with nostalgia, as if ghosts of faded glamour haunt the peeling paint and untamed tropical gardens, yet bafflingly few of the hotels have downgraded their prices accordingly. San San Tropez is one of the few affordable options (just blowing our £100 budget), with spacious, comfortable rooms around a small pool. It's a minute's stroll away from a crescent of creamy white beach you're pretty much guaranteed to have all to yourself, and the famous Blue Lagoon and Frenchman's Cove (pictured) are a few more minutes' away.
• sansantropez.com, double rooms from €900 a week including breakfast and taxes
Harmony Hall Cottages, Ocho RiosHarmony HallThese two cottages for two were built by the owners of a local art gallery, and everything about them exudes artful individual style. The wooden two-storey cottage has an outdoor bathroom overlooking the ocean, while the other is less characterful but more spacious, amid lush tropical gardens. Thoughtfully equipped with proper kitchens, Wi-Fi and iPod docks, and brimming with all sorts of art, they feel like proper homes. Higgledy-piggledy stone steps lead down to the sea, passing private sun decks. The owners' home sits between the two cottages, and their cheerful informality and warmth have a great deal to do with the relaxed intimacy.
• harmonyhall.com, cottages from $130 a night (three-night minimum)
Great Huts, Boston Bay, near Port Antonio, PortlandPhotograph: AlamyNothing can quite prepare you for the shock of what lies behind a plain wooden gate at the end of a scruffy little track. You step through it into a kind of tropical Narnia fantasy – an African village carved into a Brazilian rainforest above thundering Caribbean waves, less like a hotel than a hallucinogenic movie set. The huts – some tiny, some big enough to sleep a large family – are dotted among dense tropical vegetation. They're crafted out of bamboo and rock with batik drapes. A cliff-top bar features thrones carved out of stone, gazing out over crashing waves next to a swimming pool perched on the edge of a sheer rock face, while steps lead down to a private sandy beach. You'll need plenty of mosquito repellent.
• greathuts.com, from $60 a night B&B (two-night minimum) plus taxes
Calabash House, Treasure Beach, St ElizabethIt's almost impossible to believe you can get all this for less than £60 a night. The guesthouse's four rooms are all massive – some can sleep six – with hot water and air conditioning, while the garden groans with mango trees. A path leads through a riot of flowers past a little wooden cottage (also for rent), to a quiet sandy beach where you can buy fresh lobster from fishermen. Suzette, the hugely likeable cook, will make fantastic local meals for a modest charge, but otherwise guests share the huge kitchen and living room.
They can be an eclectic mix – I mingled with Hungarian backpackers, retired Austrian teachers, and a middle-aged Midwestern couple – which might have felt a bit like an experimental house party if it weren't for owner Elizabeth's remarkable gift for hostessing. An American artist, she lives in a cottage in the garden and never seems to stop laughing; she runs an art gallery next door, and her mosaic artwork shimmers across the guesthouse walls. It would be worth a stay here just to hang out with Elizabeth, and if you book the garden rental cottage you share her open-air kitchen and outdoor shower.
• calabashhouse.com, rooms/cottages from $75 a night plus 10-15% staff tip
Jakes, Treasure Beach, St ElizabethBack in 1996, when Jake's was just a handful of cottages in a remote fishing village, it won the Tatler award for best hotel for under £100 a night. Since then it's evolved into a world-class collection of boutique rooms and villas, the destination of choice for every international hipster looking for tropical chic without risking bumping into Simon Cowell. A beautiful spa, daily yoga classes and beachside seafood restaurant have all been added, along with rooms built on stilts over the ocean, honeymoon suites, rock star villas …
Yet Jake's is still far and away the best beachside hotel in Jamaica for less than £100 a night. Even the cheapest rooms are an aesthetic delight, though the real joy of Jake's remains not the status of your room but the rare laid-back charm of sitting at the beachside bar with a supermodel on one side, villagers playing dominoes on the other.
• jakeshotel.com, from $95 a night (two- or three-night minimum) plus taxes
Ital Rest, Great Bay, St ElizabethIf you're looking for hardcore authentic Rasta Jamaica it's hard to beat Ital Rest, two wooden two-storey cottages, thatched with palm fronds, at the end of a dirt track among tamarind, sweetsop and palm trees. The four rooms are simply furnished, and from your balcony you can watch the sun set into the ocean, across a goat field that slopes down to a coastline dotted with tiny sandy coves; the darkness is sudden, and the rooms have no electricity, just candles and hurricane lamps. The cottages have kitchens and bathrooms, and share an outdoor shower, and the Jamaican co-owner's wife cooks spectacularly good Ital food (the vegetarian diet followed by many Rastafarians), with vegetables from their organic farm. Be sure to ask for some of her guava and ginger juice.
• italrest.com, from $40 a night
River Lodge, Strawberry Fields, St MaryThis is pretty much the definition of off-the-beaten-track perfection, at the end of a pot-holed lane that peters away into a dirt track overlooking a deserted cove. A stone fort built by the Spaniards in the 17th century, it has a river curling through its lush gardens, with steps carved out of roots and vines leading down to a plunge pool. The five rooms are cool, airy and simple, arranged around a courtyard with an open-air dining area; lawns are dotted with snoozing dogs and clucking hens. The German owner is married to a Jamaican farmer and fisherman, whose vegetables and fresh fish supply the kitchen, and at night guests gather near the water's edge round an open fire beside an alfresco bamboo bar.
• river-lodge.com, from $25 a night B&B