Vacation Rentals & Houses in Jamaica

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1,375 houses

Villa Amana (up to 20 persons)

Hopewell villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 24

Match: Microwave Private outdoor pool (unheated) Sea view Staffed property Swing set or jungle gym Golf course on site or within 15 min walk

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Price per night from

$5,280

Villa Amana (up to 16 persons)

Montego Bay villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Microwave Private outdoor pool (unheated) Sea view Staffed property Swing set or jungle gym Golf course on site or within 15 min walk

All filters match

Price per night from

$4,519

Villa Amana (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Microwave Private outdoor pool (unheated) Sea view Staffed property Swing set or jungle gym Golf course on site or within 15 min walk

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Price per night from

$3,350

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Meraki Moments Villa Jamaica

Runaway Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

5 of 6 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property, Swing set or jungle gym

5 of 6 filters match

Price per night from

$345

Bee Happy

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$1,028

Dragon Fly - Your Unique Beach View Paradise

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

4 of 6 match: Microwave, Swing set or jungle gym, Golf course on site or within 15 min walk, Private outdoor pool (unheated), Sea view, Staffed property

4 of 6 filters match

Price per night from

$4,065

Ma Moura

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$2,655

Bali Hai

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$2,413

Poinciana

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$840

Following Seas (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$4,846

Hummingbird House (up to 14 persons)

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$5,307

Jamaica Villa Nutmeg, Montego Bay, Jamaica

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

“Being in Paradise” The Villa was more than I could have Dreamed!! My friends and I decided to take a trip and then experience was breathe taking. The staff made us feel like Kings and Queens and it was AMAZING. I highly recommend if travel with a large group!

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$1,603

Hummingbird House (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$4,844

Following Seas (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$4,383

Hummingbird House (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$4,383

Ambiance Sea Salt (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$3,303

Following Seas (up to 8 persons)

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$3,355

No Problem

Hopewell villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$1,269

Oceana - The Epitome of Caribbean Sophistication

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

4 of 6 match: Private outdoor pool (unheated), Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property

4 of 6 filters match

Price per night from

$4,261

Aqua Bay - New Kind of Ocean Vibe

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

4 of 6 match: Private outdoor pool (unheated), Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property

4 of 6 filters match

Price per night from

$3,425

JAMAICA HILLTOP PARADISE (YOUR CASTLE AWAITS YOU)

Runaway Bay house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$1,245

Love and Livity (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$4,081

Love and Livity (up to 8 persons)

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$3,650

Ambiance Sea Salt (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$3,963

Love and Livity (up to 6 persons)

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$1,933

Unwind at Richmond (near Ocho Rios)

Priory house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

4 of 6 match: Private outdoor pool (unheated), Staffed property, Golf course on site or within 15 min walk, Microwave, Sea view, Swing set or jungle gym

4 of 6 filters match

Price per night from

$137

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$803

Villa Turrasann

Runaway Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$660

Tennsville

Ironshore villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$322

Cool's 1 Bedroom, On the Beach, Beach & Garden View, WiFi, Ground Floor

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

5 of 6 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property, Swing set or jungle gym

5 of 6 filters match

Price per night from

$132

Serendipity Jamaica - You won't want to leave!

Rose Hall villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

“A vacation like no other” We were greeted at the airport by Norman, the most professional driver ever, he made our transition smooth and for a group of 12 adults, that is tough! He had thought of everything - including bringing a second van for our luggage! The staff at the villa greeted us at the door with warm smiles and cool towels, they made sure all our luggage was safely delivered to our rooms and then the fun began! We all stopped and stared at the huge view of the Caribbean Sea spread out in front of us, the breeze, the way the rooms are laid out and the villa itself takes total advantage of that view. We quickly changed, and began the most perfect seven days of nothing but relaxing, laughing and eating punctuated by an occasional sightseeing trip. Derek, the butler completely made the trip, he was attentive, but quiet, helpful but never intrusive - he made us feel so special. Ruby, the cook gave us gormet meals three times a day. We discussed our likes and dislikes the first day and she made it all happen. We did not need to go out to dinner and the one night we went to a lovely restaurant in town, we all agreed that we could have stayed home and eaten at Restaurant Ruby for an even better meal. It is tough to please 12 distinct people, but the staff and managment at Serendipity did just that, from organizing the most incredible massage at the villa, to driving us to out of the way Mayfield Falls, they never stopped working. All the rooms were large and private, we never felt on top of one another, we ate meals in different places, by the pool, in the dining room, on the deck, where ever we felt inspired to eat that day, Derek made it happen. I do not have one bad thing to say - I loved every minute, and would recommend Serendipity to a group like us, a large family, or just a few people that want to get away - It was truly a vacation to remember.

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$826

Villa Sweet Villa Luxury Vacation Rental - 9 BD with Full Staff Montego Bay

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 21

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$2,869

Jetaway Montego Bay (Entire Villa)

Ironshore villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 25

5 of 6 match: Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Private outdoor pool (unheated), Sea view, Staffed property

5 of 6 filters match

Price per night from

$2,524

VacationVillas Runaway Bay Spacious 1 Bedroom Apartment .

Runaway Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

4 of 6 match: Private outdoor pool (unheated), Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property

4 of 6 filters match

Price per night from

$172

Vacation Villas Runaway Pool View 2 Bedrooms and Bathrooms

Runaway Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

4 of 6 match: Private outdoor pool (unheated), Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property

4 of 6 filters match

Price per night from

$345

Vacation Villas Runaway Bay Mountain View 2 Bedroom and 2 bathrooms,

Runaway Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

4 of 6 match: Private outdoor pool (unheated), Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property

4 of 6 filters match

Price per night from

$345

Vacation Villas Runaway Bay Large Three Bedroom, Three Bathroom Apartment

Runaway Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

4 of 6 match: Private outdoor pool (unheated), Swing set or jungle gym, Golf course on site or within 15 min walk, Microwave, Sea view, Staffed property

4 of 6 filters match

Price per night from

$517

New Kingston Serenity At The Oxford

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

4 of 6 match: Private outdoor pool (unheated), Sea view, Golf course on site or within 15 min walk, Microwave, Staffed property, Swing set or jungle gym

4 of 6 filters match

Price per night from

$69

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