Vacation Rentals & Houses in Jamaica

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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: Private outdoor pool (unheated) Safe Sea view Golf course on site or within 15 min walk

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Price per night from

$825

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: Private outdoor pool (unheated) Safe Sea view Golf course on site or within 15 min walk

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Price per night from

$974

Jetaway Montego Bay (Entire Villa)

Ironshore villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 25

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

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Price per night from

$2,530

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: Private outdoor pool (unheated) Safe Sea view Golf course on site or within 15 min walk

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Price per night from

$1,603

Tennsville

Ironshore villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$322

Fall In Luxury: Villa Sweet Villa Montego Bay - 9 Spacious Bedrooms with Chef

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 21

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

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Price per night from

$2,875

Topaz Villa

Runaway Bay villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$57

Ma Moura

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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

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Price per night from

$2,641

Villa Amana (up to 20 persons)

Hopewell villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 24

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

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Price per night from

$5,252

Hummingbird House (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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

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Price per night from

$4,351

Love and Livity (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

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Price per night from

$4,059

Following Seas (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

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

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Price per night from

$4,351

Villa Amana (up to 16 persons)

Montego Bay villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

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

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Price per night from

$4,485

Ambiance Sea Salt (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

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Price per night from

$3,279

Love and Livity (up to 8 persons)

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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

All filters match

Price per night from

$3,623

Hummingbird House (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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

All filters match

Price per night from

$4,809

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

All filters match

Price per night from

$173

Following Seas (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

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

All filters match

Price per night from

$4,820

Bali Hai

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

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Price per night from

$2,400

Love and Livity (up to 6 persons)

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

All filters match

Price per night from

$1,918

No Problem

Hopewell villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

All filters match

Price per night from

$1,262

Ambiance Sea Salt (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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

All filters match

Price per night from

$3,944

Villa Amana (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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

All filters match

Price per night from

$3,325

Following Seas (up to 8 persons)

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

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

All filters match

Price per night from

$3,330

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

Dragon Fly - Your Unique Beach View Paradise

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

3 of 4 match: Safe, Golf course on site or within 15 min walk, Private outdoor pool (unheated), Sea view

3 of 4 filters match

Price per night from

$4,074

Luxury Life Villa

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$276

Anticipation - Anticipate Your Escape

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$2,877

Avalon Villa - Your Restful Hideaway

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$1,462

Vacation Villas Runaway Pool View 2 Bedrooms and Bathrooms

Runaway Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 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

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 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

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$518

Bali Hai - Rejuvenate and Recharge

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$2,054

Bumpers Nest Villa - Elegant Caribbean Living

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$2,988

Bella Vista Villa - Highest Standards of Luxury and Comfort

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$3,943

The Cozy Haven by the Beach

Lucea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$115

Little Palm

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Sea view, Golf course on site or within 15 min walk, Private outdoor pool (unheated), Safe

3 of 4 filters match

Price per night from

$940

Serene Room 2

Ironshore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Private outdoor pool (unheated), Sea view, Golf course on site or within 15 min walk, Safe

2 of 4 filters match

Price per night from

$75

VacationVillas Runaway Bay Pavilion View 2 Bedroom Apartments.

Runaway Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk, Safe, Sea view

3 of 4 filters match

Price per night from

$345

Viewing 38 of 1,035
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