Vacation Rentals & Houses in Jamaica

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1,359 houses

JAMAICA HILLTOP PARADISE (YOUR CASTLE AWAITS YOU)

Runaway Bay house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$1,238

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$799

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.

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$822

Luxurious Ocho Rios Waterfront Villa: Private Pool, BBQ, Chef, Nr. Attractions

Tower Isle villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

“My stay here was heaven on earth.” My stay on this villa was great. Everything I could imagine and more Food was delicious and authentic; not process or frozen. The master suit where I stayed was immaculate. The power shower to the huge jacuzzi bath. The king size bed made my night rest wonderful. It's felt like I was sleeping on clouds. This villa was hard for me to leave, from pool, xbox, board games and a fantastic pool why must I go outside.(lol). When I decided to go outside it was also a great and wonderful experience. I visited duns river falls, when to the hot spot night club margarita ville, oceans 11, and amnesia. We sang karaoke had great Jamaica drinks and watch the beautiful scenery. All these great attraction only 12mins tops from the villa. However my highlight of the stay is the private beach, only 2min walk from the villa. Great vacation I'm booking another stay for January andirons can't wait...

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$970

Jetaway Montego Bay (Entire Villa)

Ironshore villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 25

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$2,510

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!

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$1,597

Tennsville

Ironshore villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$320

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

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 21

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$2,852

Villa Turrasann

Runaway Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$658

Ma Moura

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$2,642

Poinciana

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$835

Villa Amana (up to 20 persons)

Hopewell villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 24

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$5,253

Hummingbird House (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$4,362

Love and Livity (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$4,060

Following Seas (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$4,362

Villa Amana (up to 16 persons)

Montego Bay villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$4,497

Ambiance Sea Salt (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$3,288

Love and Livity (up to 8 persons)

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$3,633

Dragon Fly - Your Unique Beach View Paradise

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$4,042

Bee Happy

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$1,023

Hummingbird House (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$4,821

Hummingbird House (up to 14 persons)

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$5,281

Following Seas (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$4,821

Bali Hai

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$2,401

Love and Livity (up to 6 persons)

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$1,923

No Problem

Hopewell villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$1,263

Ambiance Sea Salt (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$3,945

Villa Amana (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$3,334

Following Seas (up to 8 persons)

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Stove Private outdoor pool (unheated) Sea view Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$3,339

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

Following Seas - Mesmerizing Views

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$3,765

Karma Bay - A Taste of Paradise

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$3,474

Oceana - The Epitome of Caribbean Sophistication

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$4,237

Aqua Bay - New Kind of Ocean Vibe

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$3,406

Elysian Plain - The Edge of the Caribbean Sea

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$1,793

Eureka - A Jamaican Great House

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$1,712

No Le Hace - Fabulous Unobstructed Ocean Views

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$1,613

Pineapple House - Captivating Views of the Caribbean Sea

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$3,260

Oceans 8 - Blue Waters of the Caribbean Sea

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

4 of 5 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Stove, Sea view, Staffed property

4 of 5 filters match

Price per night from

$7,601

Viewing 38 of 1,359
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