Sandy Bay Rentals

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70 Houses

Anticipation Villa at The Tryall Club

Sandy Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$3,925

Island House at Tryall Club

Sandy Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$851

Great rentals within 20 miles that match your search

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!

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Price per night from

$1,607

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.

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Price per night from

$827

2 Bedroom Apt, 6 Minutes away from Airport Montego Bay

Montego Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Looks exactly like the pics.” I would stay here every trip to Mo Bay!!! The owner met me at the airport on time, was friendly and offered a ride. Since I already had a ride we followed him to the property. If I was not with a local I would of got lost for it was several twist and turns before entering the locked gates of the property. Close drive to everything. The neighbors were friendly. As I entered the 3rd floor apartment it felt like home. Every room looks like the pictures posted. We were provided pots, utensils, plates, drinks (liquor), wifi, cable, stereo system, telephone, linens, basically everything as if you were home except for food. Ac is only in the master bedroom however there was a breeze during the day (please note I traveled in October when it is much cooler in Jamaica). The first day I took a cold shower but the rest of the days I had hot water. I like nice views and I could see the ocean from the living room. Thanks Ian!!!

Responds fast! avg. 3 hours 53 minutes

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Price per night from

$80

Star Apple House, Montego Bay, Jamaica

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$173

Datura Villa

St James, Montego Bay villa

  • 5 bedrooms
  • 15 bathrooms
  • sleeps 10

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Cozy Cottage in the Hills

Rose Hall house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$115

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Price per night from

$299

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

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 21

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Price per night from

$2,869

Hidden Gem Suites

Rose Hall b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$80

LaVue

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$132

Cozy & Safe Seawind On The Bay Studio Apartment Free Beach Access OLR

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$91

Suite Eleven

Ironshore apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$109

NICKELS GARDEN VILLAS

Montego Bay villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$117

Luxury Jamaican Villa Overlooking Caribbean Sea

Hopewell villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$2,525

Blue Heaven Villa

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,148

Clean, Quiet Oceanview Cottage in Oceanpointe, Lucea Hanover

Lucea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$167

Montego Bay Vacation Apartment - The Best Views

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 44 minutes

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Price per night from

$64

Luxury Oceanfront Residence Condo with Pool in Montego Bay

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$459

Luxury 2BR Oceanfront Condo w/ Pool Access in Montego Bay

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$459

Enjoy Sunsets! Luxury Fully-Equipped 3BR Apt w/ Pool in Montego Bay

Montego Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$689

NEW LISTING! Renovated Luxury Unit w/ Community Pool, Gym + More

Montego Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$804

Calabash Place

Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$83

Bee Happy

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$1,025

Ma Moura

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$2,645

Bali Hai

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,404

Aqua Bay

Hopewell villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$4,226

Trinity

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$3,761

Little Hill

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$3,102

Poinciana

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

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Price per night from

$836

Etoile

Hopewell villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$627

Little Palm

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$941

Mirador

Hopewell villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$523

Hanover Grange (up to 18 persons)

Hopewell villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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Price per night from

$4,044

Sea Glass ( up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$3,243

Ambiance Sea Salt (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$3,949

Harmony Hill (up to 14 Persons)

Hopewell villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$5,224

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