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Rental

Modern two-story tropical villa with glass balconies, wooden deck, orange lounge chairs and a clear blue pool with lush greenery and ocean views.

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 2

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 4

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 5

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 6

Sunlit coastal-style bedroom with blue walls and upholstered queen bed, yellow curtains, wall air conditioner, nightstand lamp and fresh flowers

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 8

Cheerful coffee station with mint-green cabinets, white countertop, two coffee makers and kettle, wooden floating shelves with mugs and potted plants, and a black chalkboard that reads 'Welcome to Jamaica!'.

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 10

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 11

Bright modern kitchen with sage-green lower cabinets, white upper cabinets, white countertops, stainless steel built-in microwave and oven, farmhouse sink under a window, wood floors and open shelving with decor.

Bright modern kitchen with green lower cabinets, stainless double-door refrigerator, stainless range hood, white quartz island with wood breakfast bar and gooseneck faucet, open wood shelves, and a fruit bowl of bananas.

Modern backyard patio with wicker lounge chairs and sliding glass doors beside a curved swimming pool glowing electric blue at night, lit by ambient terrace lights.

Shaded tropical deck with green turf, wicker lounge chairs with red cushions and potted palms, wooden railing framing banana trees, hillside and a distant ocean view.

Aerial view of a modern two-story tropical villa on a green hillside with brown-tiled roofs, a wooden deck with orange loungers, a pergola seating area, and an elevated infinity pool and spa surrounded by lush banana and palm foliage.

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 17

Overhead view of a modern open-plan living room with warm hardwood floors, polished wooden staircase, cozy gray sectional sofa, white TV console and flat-screen TV

Cozy home bar nook with warm yellow walls, wooden countertop and corner sink, dark floating shelves holding liquor bottles, glassware, decorative signs, a small wine fridge and a potted grass planter.

Chef in white jacket and striped apron gestures toward colorful salads and roasted dishes displayed on a wooden-topped island in a modern home kitchen with stainless steel refrigerator.

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views image 21

The Rising Sun Villa: Luxury Rental with with Infinity Pool, Hot Tub & City Views

5 (11)
Sleeps 13

From $800/night

Rental

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 1

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 3

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 4

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 5

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 6

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 7

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 8

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 9

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 10

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 11

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 12

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 13

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 14

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 15

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 16

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 17

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 18

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 19

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 20

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 21

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 22

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 23

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 24

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 25

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 26

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 27

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 28

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 29

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 30

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 31

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay image 32

Bougain Villa: Luxury Villa with Staff, Pool & Half Moon Resort Membership in Montego Bay

Sleeps 12

From $2,400/night

Rental

Aerial view of a white luxury tropical villa with a curved swimming pool and hot tub, surrounded by lush palm trees and guests relaxing on the patio.

Sunny covered patio with a resort-style dining table set for eight—blue napkins, floral plates and a red tropical flower centerpiece—overlooking a curved swimming pool, loungers, white umbrella and lush palm-filled garden.

Sunlit tropical courtyard with a copper outdoor bathtub and showerhead, surrounded by lush green plants and a stone floor

Sunlit tropical twin bedroom with white linens and fringed throws, rattan headboards, matching white bedside tables and round textured lamps, wooden benches at the foot of each bed, lush greenery visible through two windows.

Sunlit twin bedroom with rattan headboards and white linens, bedside lamp and open French doors to a balcony overlooking a lush tropical garden—coastal vacation retreat.

Sunlit tropical bedroom with vaulted wood ceiling, neutral decor, dresser and lamp, wall TV, and open doors to a balcony with a white wicker chair and lush garden—island getaway vibe.

Spa-like coastal bedroom with rattan headboard and bench, crisp white bedding, green accent pillows, warm bedside lamps, and an open doorway to a bright ensuite bathroom with a glimpse of tropical greenery.

Cozy neutral bedroom with vaulted wood ceiling, king bed with green pillows, rattan bench at foot, matching bedside lamps and dappled sunlight on white bedding.

Grilled herb chicken breast drizzled with bright orange sauce on mashed potatoes, topped with a crisp cheese tuile and green beans on a white plate set on a woven straw placemat, hands nearby and a red cocktail in the background.

Sunlit tropical living room with a white sectional sofa, green accent pillows, rattan chairs, wooden vaulted ceiling and a large window framing lush garden foliage.

Cozy sunlit dining table close-up with a rum bottle and snifter of amber spirit, green vases holding leafy stems, a plate of appetizers, and a hand reaching toward the table.

Smiling server in a white polo holding three plates of golden shrimp appetizers with sauce, standing in a bright modern kitchen doorway.

Two people relaxing on white wicker lounge chairs at a sunny tropical poolside terrace, shaded by a large tree with glossy lobed leaves and round green fruits for a lush outdoor vacation vibe.

Airy open-plan coastal living and dining room with vaulted wood ceiling, rattan dining set, large windows and lush tropical plants

Bright tropical villa dining area with vaulted wood ceiling and white ceiling fans; rattan chairs around a glass table set for breakfast with orange juice and pastries, a host arranging the table beside a sunny living room and garden-view window.

Couple holding hands strolling through a sunny tropical garden framed by tall palm trees, bright orange flowers and a clear blue sky.

Sliced banana bread loaf dusted with powdered sugar on a banana leaf and wooden board, with a blurred bowl of pineapples and mangoes for a tropical kitchen vibe.

Sunny tropical villa patio with white cushioned lounge chairs and rolled turquoise towels on a balcony, surrounded by palm trees, red tropical plants and a bright blue sky.

Inviting copper freestanding bathtub in a sunlit tropical garden courtyard beneath a twisted tree, surrounded by lush green plants and a dappled stone pathway.

Bright, breezy coastal-style living room with vaulted exposed wood ceiling and ceiling fan, white L-shaped sectional with aqua pillows, round textured coffee table, rattan armchairs, indoor plants and a large window framing lush tropical greenery.

Bright airy bedroom with vaulted wood ceiling and ceiling fan, king bed dressed in white with green accent pillows, rattan chair and bench, sliding glass doors opening to a sunlit balcony overlooking lush tropical greenery — a serene coastal retreat.

Relaxing tropical spa massage: therapist giving a back massage to a client on a treatment table in a bright room opening to lush garden

Sun-drenched circular swimming pool and spa on a tropical terrace with white loungers, umbrellas, palm trees and a distant ocean view.

Sunny covered tropical villa patio with vaulted white ceiling and fans, wicker dining and lounge seating, tiled floor and round swimming pool overlooking lush greenery and blue ocean sky.

Sunny tropical villa courtyard with gray tiled roof and pointed turret, paved driveway with grass joints, lush landscaping of bromeliads, red ti plants and palms, and a glimpse of a pool under a bright blue sky

Woman practicing outdoor yoga in upward-facing dog on a blue mat on a green lawn in a lush tropical garden under an overhanging fruit tree at golden hour

Top-down view of a sliced strawberry-topped cheesecake with whipped cream and glossy strawberry sauce, served on white plates on a white serving tray.

Sunny tropical courtyard patio with stone steps, a leaning tree holding a hanging outdoor shower and orchids, white stucco wall with window and towels, surrounded by lush monstera and palm greenery.

Bright neutral luxury bathroom with marble double vanity and round mirror, glass-enclosed shower, freestanding tub, and French doors opening to a small garden courtyard

Airy sunlit tropical bedroom with rattan four‑poster canopy bed in white linens and blue accent pillows, vaulted wood ceiling with fan, wicker seating and window bench overlooking lush greenery, bedside lamp and visible en‑suite — coastal vacation rental vibe.

Sunlit coastal bathroom with glass-enclosed walk-in shower, white double-sink vanity, marble tile floor, and an open door leading to tropical palm foliage.

Abacus Villa: Complimentary Van & Driver for Stays 7+ Nights

Sleeps 8

From $1,500/night

Explore your destination through the lens of someone who’s already been there done that!

Rental

Aerial view of a luxury three-level villa on a tropical hillside with wraparound verandas and a curved infinity pool overlooking lush green hills and distant mountains.

Ocean-view indoor bar in a tropical villa with marble countertop and pendant lights; a bartender pours a cocktail at a curved wooden bar framed by a large carved shell and colorful map of Jamaica, cushioned barstools and blue sea visible through arched doors.

Tropical open-air yoga pavilion on a wooden deck with colorful mats, exercise balls, wicker pendant lights, and ocean-and-forest view.

Aerial view of a luxury tropical hillside villa nestled in lush green forest, featuring a round infinity pool and sun-soaked terrace with rolling mountains and a bright blue sky.

Oceanfront tropical villa with white columns and arched central entry, flanked by palm trees and a circular stone driveway under a bright blue sky.

Resort-style tropical bathroom with a large soaking tub, curved wooden vanities, glass-enclosed toilet and shower with blue mosaic tile, arched window looking out to palm trees, and a leaf-shaped ceiling fan.

Bright coastal-inspired hotel suite living area with a white sofa bed, blue-accent armchairs, wooden desk and coffee table, carved wooden bookshelf with ceramic vases, tiled floor, and framed botanical prints.

Airy sunlit villa bedroom sitting area with hardwood floors, tufted chaise lounge, vintage mirrored desk, ornate framed artwork and green side table with peacock sculpture

Sunlit tropical-style bedroom with king bed and patterned bedding, arched wooden shutters opening to lush greenery, wooden ceiling fan, mirrored dresser, wicker bench and cozy armchair.

Spacious spa-like master bathroom with dark wood double vanity and marble countertop, three ornate framed mirrors, wall sconces, upholstered vanity stool, patterned area rug, and mirrored sliding doors reflecting a walk-in glass shower.

Bright coastal-style master bedroom with king bed, hardwood floors, arched wooden windows with shutters, cozy seating area, ceiling fan, mirrored TV console, bedside lamps, and a potted tropical plant flooding the room with natural light.

Spacious luxury bedroom interior with dark wood four‑poster king bed, navy blue and white coastal textiles, daybed and matching armchairs, patterned blue area rug, hardwood floors, wooden armoire and TV cabinet, and a glass coffee table topped by a small dog sculpture

Billiards table on a sunlit villa veranda with cushioned chairs and white arched columns, overlooking a palm-lined stone pathway through lush tropical gardens toward green hills.

Ocean-view tropical veranda at dusk with columned porch, wicker lounge chairs and cushioned seating around a glass coffee table, warm lantern lighting and ceiling fan overlooking trees and the sea.

Tropical coastal bedroom suite with white bedding and wicker daybed, wooden built-in media desk and TV, and arched glass doors opening to a covered terrace dining area with ocean and palm views.

Bright coastal-style hotel suite living room with leaf-blade ceiling fan, dark wood built-in media wall and flat-screen TV, patterned sofa and floral armchair, wooden coffee table, framed portrait paintings and doorway to a bathroom with towels visible.

Oceanfront terrace with white columns, wicker lounge seating, infinity pool and panoramic turquoise sea view, plus al fresco dining under chandeliers and ceiling fans

Luxurious spa-like bathroom with frameless glass rain shower, curved soaking tub on tiled steps, mosaic tile walls and arched window framing a lush hillside view.

Cozy Mediterranean-inspired sitting room with carved wood furniture, cream sofa with floral cushions, glass-top desk, warm lamp lighting and dark hardwood floors, patterned doors opening to a tiled bath.

Bright luxury bathroom with a curved marble vanity and oval sink, ornate scalloped mirror, teal mosaic backsplash, glass-door turquoise tile shower, colorful red wall textile and white towels.

Sunlit tropical bedroom with light blue walls, floral-patterned bedding on a rattan bed, wooden dresser and wardrobe, arched windows opening to garden greenery, woven ceiling fan, pink upholstered chairs and ornate area rug.

Sunny coastal-style living room with turquoise accents: wicker sofa with blue cushions, patterned armchairs around a round painted table, mirrored decorative wall panels, built-in white shelving with lamps and vases, and polished dark hardwood floors.

Coastal-chic boutique hotel bedroom with tufted turquoise headboard, crisp white bedding, built-in shelves and lamps, large white armoire, round turquoise table and patterned chairs on dark hardwood floors.

Bright luxury bedroom interior with large teal tufted headboard, crisp white bedding, teal accent pillows and lamps, built-in white shelving and a central orchid arrangement.

Ocean-view spa treatment room with a massage table, wide wooden-framed windows revealing tropical palms and sea, decorative plants and orange flowers, and a smiling spa therapist in a white uniform.

Relaxing ocean-view tropical veranda — spacious covered outdoor lounge with cushioned sofas and armchairs, ceiling fans and lanterns, tiled floor and palm trees visible beyond the white railing

Ocean-view Mediterranean-style covered terrace with exposed wooden beams, columned walkway, rattan and upholstered lounge seating, chandelier lighting and arched glass doors to an indoor bar.

Resort-style spa treatment room with a central massage table draped in white linens, wicker lounge chairs, curved aqua mosaic wall, tropical potted plants, warm pendant lighting and neutral tile floor.

Oceanfront infinity pool overlooking turquoise sea with white lounge chairs, tropical palms and a bright blue sky with wispy clouds

Infinity-edge pool at a tropical coastal villa with palm trees, lounge chairs, and a bright blue sky

Flower Hill Villa: Montego Bay's Most Luxurious Private Home Rental

Sleeps 20

From $3,150/night

Rental

Villa Rosa: Luxury Ocean-View Villa with Private Gym, Spa, and Half Moon Club Access image 1

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Villa Rosa: Luxury Ocean-View Villa with Private Gym, Spa, and Half Moon Club Access

Sleeps 10

From $2,000/night

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