St James, Montego Bay Rentals with Pools

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195 Houses in St James, Montego Bay with pools

Windfall Villas... FREE TRANSPORTATION !

St James, Montego Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

Match: Swimming pool

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Price per night from

$344

Mobay Club Studio Hip Strip, Beach Pool Nightlife

St James, Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$137

Million Dollar View/ Centrally Located 1BR

St James, Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$114

Datura Villa

St James, Montego Bay villa

  • 5 bedrooms
  • 15 bathrooms
  • sleeps 10

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Beautiful Luxury 1 BDRM Condo

St James, Montego Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$218

Windfall Villas... FREE TRANSPORTATION AND MAID

St James, Montego Bay villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$344

*PLEASE ENQUIRE FOR SPECIAL RATES* 5 Bedroom Fully Staffed Villa with Ocean View

St James, Montego Bay villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$1,358

Great rentals within 20 miles that match your search

Island Breeze Villa

Montego Bay villa

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$329

StepAway

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 22 minutes

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Price per night from

$87

Dream Castle Villa, Montego Bay Jamaica

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 20

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Price per night from

$1,323

Sailing, Montego Bay, Pool, Beach, 876, Jamaica

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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Price per night from

$91

Hospitality Expert NSC: Beach front, Pool & Chef

St.Bran's Burg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 50 minutes

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Price per night from

$160

Sushine at Sea Castle

Rose Hall apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$75

Lavish Townhouse, Beach Access, Pool, Gym w/ CPT

Montego Bay house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 47 minutes

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Price per night from

$265

Foxtail Villa

Ironshore villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$841

Blue Heaven - 3 Bedroom in Montego Bay - Book Now

Montego Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$716

Serenity on the Beach - 4 Bedroom Villa at Montego Bay - Book Now

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,251

About The Sunrise Pool And Beach Access

Rose Hall apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$67

Chic View 1Bedroom, 10 mins away from the Airport

Ironshore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$195

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Price per night from

$98

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Price per night from

$169

Hospitality Expert TTV - Pool, Beach, Chef

Rose Hall villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 14

Responds fast! avg. 50 minutes

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Price per night from

$1,145

Fairway Manor - 7 Bedrooms - Montego Bay

Montego Bay house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$2,210

Great River House - Montego Bay 5 Bedrooms

Montego Bay house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$1,857

Flower Hill - Spring Farm, Montego Bay 6 bedrooms

Montego Bay house

  • 6 bedrooms
  • 14 bathrooms
  • sleeps 12

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Price per night from

$3,714

Endless Summer - 6 Bedrooms - Spring Farm

Montego Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$2,429

Thomas House - Spring Farm, Montego Bay 7 Bedrooms

Montego Bay house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$1,800

Sunrise Villa - Tryall Club 4 Bedroom Oceanfront

Montego Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$643

Two Bedroom one bathroom

Ironshore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$115

Second floor three bedroom three bathroom Apartment

Ironshore apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$178

Villa Windy Way

Ironshore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

Nautical Homes Miramar

Montego Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Holiday Home” My daughter and I rented this really beautiful villa. Angie collected us from the airport and kindly took us shopping to get some food to tide us over until we picked up our rented car. The house smelled fresh as we walked in. The lounge is spacious with three and two seater settees, coffee table and a large smart TV on the wall. The villa has air-conditioning in the lounge and both bedrooms that was much appreciated as it was sometimes 35 degrees outside. Bedrooms have TVs on the wall. There is a large round thick glass dining table with 4 chairs. The kitchen has a fridge-freezer, gas cooker, microwave, kettle, coffee maker, toaster and a washing machine that my daughter thought wonderful as she used it often. Everything is as described in respect of this villa. We had a wonderful stay and will definitely return when next in Jamaica. Another thing we thought wonderful is the automatic gates - no getting out and opening the gate - just press the remote control, drive in and park! The security company checked the house and left a note to say they have been round. We felt very safe at the villa. If you do not rent a car, Bouge taxis can be found who will take you where you want to go or ask Angie. There is a very smart car for rental should you need it at the villa. We did not hire this car as we had previously booked a 4 x 4 to take us cross country to St. Catherine and other areas that had rough terrain. We were not bothered by anyone - complete freedom. Well done Vinroy. Best wishes Dorothy and Adella.My Response Thank you very much for that wonderful review! Looking forward to having you and your daughter again. Thanks much

Responds fast! avg. 25 minutes

Match: Swimming pool

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Price per night from

$457

Jamaica Villa Nutmeg, Montego Bay, Jamaica

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

“Incredible view & fantastic staff” My family and I (7 adults & 1 child) just returned from Nutmeg Villa and we had a wonderful time!! Upon entering the Villa, there is a breathtaking view of the pool, the gardens and the sea which can't be beat. The rooms were spacious and suited our group well, especially the downstairs bedroom with the pool table and the games. We all agreed that the best aspects of our vacation were having a private pool and the staff at Nutmeg. The staff went above and beyond to make sure we were enjoying ourselves to the fullest and we did! On behalf of my family we would like to send a heartfelt thank you to Chef Morgan, Carlington, Ms. Ann, Ms. Cathy, Garrett, Wayne, Dave and Donovan (the security guard) for making our vacation unforgettable.

Match: Swimming pool

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Price per night from

$1,603

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: Swimming pool

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Price per night from

$1,031

Cozy Montego Bay Studio Apartment Jamaica

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful apartment - Can Not Wait to Come Back” Lovely stay! Really clean apartment great for 2. Store downstairs was so easy to get groceries to make lunch. Alyssa made it into a kingsize bed for us last minute, and she was great arranging a driver to drop us at the airport for our 9am flight. Very cool location, we woke up every morning and walked right across the street to the beach. (Theres a free local beach if you keep walking to the left, but Docs Cave was worth the 5 bucks) Best part is everything you need you can walk to. The building is old but the apartment made up for it- we saw a couple others with their doors open and we felt lucky to get an updated one. And we got beach towels provided. Cant wait to go back. Thanks alyssa

Match: Swimming pool

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Price per night from

$114

Beautiful Exotic Tropical Paradise - Townhouse in

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Just wow!” Very pleasantly surprised with the modern conveniences and comfort of this home in paradise. The location was central and easy to find. This will definitely be the way to spend vacations as opposed to a resort. Very relaxing. Well taken care of grounds and pool. Highly recommend.

Match: Swimming pool

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Price per night from

$269

Holiday House & Hill Top Villa Montego

Ironshore apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$184

Gorgeous Oceanview Condo Montego Bay Jamaica

Montego Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

“A great place to stay!” We spent three wonderful days at alyssa's Condo in the heart of Montego Bay. It is in a quiet, gated community, with a 1 minute walk to Doctor's Cave beach. What more could you ask for? The condo is clean, and everything stated in her description is accurate. Alyssa is easily contacted and has a very pleasant demeanor. When we left her condo to continue the rest of our vacation in another parish, an iphone was left behind. Alyssa immediately contacted her cleaning lady and the iphone was left with the reception. We picked up the iphone 4 days later. Thank you alyssa for being so accommodating and we would definitely like to stay with you again on our next visit. Highly recommended!!

Match: Swimming pool

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Price per night from

$331

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