St James, Montego Bay Rentals with Pools

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267 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

$345

Mobay Club Studio Hip Strip, Beach Pool Nightlife

St James, Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$137

Ocean Front Modern Luxury Condo Montego Bay Club

St James, Montego Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$171

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

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Price per night from

$345

Great rentals within 20 miles that match your search

Penthouse In Paradise, 3 bdrm incl. housekeeper

Montego Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 0 minutes

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Price per night from

$373

Caribbean Sea Dreams, 2 bdroom with housekeeper/cook

Montego Bay townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 0 minutes

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Price per night from

$230

TWIN PALMS RETREAT - MONTEGO BAY JAMAICA

Montego Bay townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$414

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Price per night from

$917

Ocean Front Modern Studio Hip Strip Beach Mobay

Montego Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$171

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$861

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$804

Calming Waters Riverside Villa & Yoga Retreat

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$201

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

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

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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.

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Price per night from

$270

Chaudhry at Holiday House Montego Bay

Ironshore apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$207

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!!

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Price per night from

$332

Bruce Seacastles Vacation Penthouse

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“awesome” arrived at seacastle with a few friends for a girls weekend. The condo was nice,clean and very spacious. Everything was ready when we got there and the owner very courteous and even helped us with an extra night when we missed our flight.the hotel next door had a great bar and we enjoyed our stay very much. I would definitely recommend seacastle for a great relaxation trip

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Price per night from

$194

2-br watervu apt-Seawind onthe Bay,Montego Bay,Jam

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$213

High View Villa

Montego Bay villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$689

Allamanda - Montego Bay 5 Bedrooms

Montego Bay house

  • 5 bathrooms
  • sleeps 2

Match: Swimming pool

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Price per night from

$1,718

Luxurious 1 BdRm Ocean Front Condo in Montego Bay

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“WONDERFUL TIME!” Property is beautiful....This is my second stay at the Palmyra and once again we had a wonderful time. This is a condo that is built on the most beautiful beach there is in Montego Bay, between the former Ritz Carlton and Hilton Rosehall hotels. We had views of both beach and mountains. I can still feel the tradewinds. Sharon, the owner is most gracious and the staff there was very attentive and accomodating. Thank you all, So, Sharon Im ready to book my vacation for Feb, 2015. This time NO KIDS. Looking forward til Feb. Denise

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$224

Bogue Villa

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“R & R at it's Finest!” I have stayed at this Villa three years in a row and am planning on going again for 2 weeks in February 2015! It is relaxing, comfortable and spacious and the staff are amazing as Sophia is the best and will make your stay incredible. I can't wait to return for my 4th visit!

Responds fast! avg. 3 hours 54 minutes

Match: Swimming pool

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Price per night from

$173

Serendipity - Spring Farm, Montego Bay 6 Bedrooms

Montego Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 1

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Price per night from

$1,584

Summerhill - Spring Farm 9 Bedrooms (ask about our 4-8 bdrm rates)

Montego Bay house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Swimming pool

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Price per night from

$1,991

Nutmeg - Spring Farm, Montego Bay 6 Bedrooms

Montego Bay house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“The best vacation ever at the best villa with the best staff” Alan & Reg, We had a fabulous time at Nutmeg! All six of us loved this villa/property. The ocean view was heavenly. All of the bedroom were great, and the master was simply beautiful. The staff was outstanding! We fell in love with all of them; Ms. P, Carlington, Nataleen, Shereen, Andre and Wilton. They were very professional and all were great at their jobs. Ms. P is an excellent chef. We loved each meal! We plan to retun to Nutmeg next year! We wish we could buy this property. I was told that it would be going on the market soon, however, we are sure that it will be too pricey for us. So, for now, we will just have to visit yearly. Thanks so much for all of you assistance, you all were fabulous, too! Sincerely, Rodney & Neshanta Banks Reginald & Belinda Burney Ruben & Pam Tillman

Match: Swimming pool

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Price per night from

$1,654

Drambuie - Montego Bay 5 Bedroom

Montego Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,160

5 Bedroom Luxury and Affordable Villa on 9 acres

Wiltshire villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

“Quiet, Crazy Wonderful” Dutura - Peaceful, beautiful, quiet, lush, green, roomy, comfortable, spacious! Dutura Staff - Amazing, kind, caretakers, fun, Great Cooks, great trainer, attentive, major attention to details that make you feel comfortable. Those are the words that describe this place. We were met with warmth and smiles. Chisholm took us to some great spots for Crazy adventures but really safe. Then home to an amazing staff that felt like family from day one! We stepped out of our comfort zones, we rested, we ate, we laughed, we Yogaed, we walked in beauty, we were challenged and we did not want to leave. Thank you Randel and Dutura for an experience we will never forget. We were the crazy 8's becoming indigenous! haha inside joke!

Match: Swimming pool

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Price per night from

$788

Celebrity Villa Jamaica

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Swimming pool

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Price per night from

$1,320

Fairway Manor - 7 Bedrooms - Montego Bay

Montego Bay house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Swimming pool

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Price per night from

$2,897

Endless Summer - 6 Bedrooms - Spring Farm

Montego Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$2,435

Great River House - Montego Bay 5 Bedrooms

Montego Bay house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$1,862

Two Bedroom one bathroom

Ironshore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$115

Chaudhry House Second floor two bedroom two bathroom Apartment

Ironshore apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$190

Villa Windy Way

Ironshore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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Price per night from

$69

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rentals in St James, Montego Bay

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