Vacation Rentals & Houses in Jamaica

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420 houses

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Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$1,718

Roaring Pavilion - Ultimate Luxury Beachfront Villa

Ocho Rios villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,466

Sea Glass Villa

Hopewell villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,303

VILLA DORA MAE

Mammee Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,061

Anticipation Villa at The Tryall Club

Sandy Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,916

Hanover Grange (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,628

Quinntessential (up to 8 persons)

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,544

Sundance (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,795

Harmony Hill (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$5,223

Hanover Grange - Exclusive Private Jamaican Estate

Montego Bay villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,092

Harmony Hill (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,729

Sundance (up to 14 persons)

Hopewell villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$5,463

Sea Glass (up to 8 persons)

Hopewell villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,190

Hanover Grange (up to 18 persons)

Hopewell villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,035

Little Waters on the Cliff - Simply Exceptional

West End villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$974

Quinntessential (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,118

Bella Vista Villa - Highest Standards of Luxury and Comfort

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,927

Bumpers Nest (up to 8 persons)

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,789

Sundance (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,483

Overlook

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,451

Bumpers Nest Villa - Elegant Caribbean Living

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,976

Sea Glass ( up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,235

Trinity

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,753

Bumpers Nest (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,793

Little Hill

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$3,095

Three Little Birds (up to 6 persons)

Montego Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$1,642

Aqua Bay

Hopewell villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,216

Harmony Hill (up to 14 Persons)

Hopewell villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$5,212

Sea Glass (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,697

Three Little Birds (up to 8 persons)

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,190

Hanover Grange (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,957

Bali Hai - Rejuvenate and Recharge

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$2,045

Villa De-luxe Paradise Vacation Home

Discovery Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$1,145

These homes match some but not all of your filters. Clear all filters

Heartland BnB

Petersfield b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$58

Villa Sorrento - Your Beautiful Paradise

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$1,088

Linga-Awile - Your Private Beachfront Villa

Discovery Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$595

Willows villa

St. Ann's Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$281

Bougainvillea House - Unreserved Luxury

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,530

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