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Montego Bay Rentals with Pools

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Montego Bay Rentals with Pools

371 vacation rentals

Cozy Cove - 5 Bdrm Villa w/Pool, Gated Community

Montego Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

“Jamaican Paradise!” Cannot truly express how fabulous this trip has been, Jaime from the very beginning has been gracious, warm and very accommodating. Her rental has been nothing but spectacular! It is exactly and more than what the pictures convey.

Price per night from

$900

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Goat Hill

Hopewell villa

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$1,000

1 / 73

BREATH-TAKING JAMAICAN PARADISE

Rose Hall villa

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$155

1 / 11

Passion Fruit

Ironshore b and b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$30

1 / 33

PROMOTION! COMPLEMENTARY DRIVER/VAN FOR WEEK- LONG STAY GOOD FROM 3/1 - 9/30

Montego Bay villa

6 bedrooms / 6 bathrooms / sleeps 12

“So great I already booked next year” Sorry guys the 14-21 of May is ours.I encourage anyone whose reading this to snag one of the other weeks. Absolutely the only way to travel. I work long hours in a hectic industry, I take any free time with my fam

Responds fast! avg. 3 hours 55 minutes

Price per night from

$1,286

1 / 32

Anticipation - Tryall Club

Hopewell villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$2,241

1 / 22

The Wharf House - Old World Charm By The Sea

Montego Bay villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$640

1 / 20

Penthouse In Paradise, 3 bdrm incl. housekeeper

Montego Bay apartment

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 4 minutes

Price per night from

$325

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Enchanted Villas For the holiday of a life Time

Ironshore villa

10 bedrooms / 9 bathrooms / sleeps 18

Price per night from

$650

1 / 18

Chateau de La Rose Ocean Breeze Room

Ironshore apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 56 minutes

Price per night from

$100

1 / 6

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

Montego Bay apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$125

1 / 29

Annabella - Tryall Club

Hopewell villa

6 bedrooms / 8 bathrooms / sleeps 12

Price per night from

$1,714

1 / 14

Private Beachfront Condos in Montego Bay Jamaica

Rose Hall apartment

1 bedroom / 1 bathroom / sleeps 4

“I will go back anytime” Before our departure, the booking was very professional. Debra advised us well, and she was very patient with us. On our arrival, we were greeted by Karen as if we were family returned to the country for a long absence. We had

Price per night from

$84

1 / 6

Beautiful ocean views, Montego Bay Studio near Doctors Cave Beach and Hip Strip

Montego Bay apartment

1 bedroom / 1 bathroom / sleeps 2

“Vacation at Montego Bay Studio apt. 35a” We surely did enjoy our stay at No 35a. Initially we had made arrangements for a stay of one week at No 35a in Montego Bay and one week at another Hotel in Kingston. After our first two days at No. 35a we did

Price per night from

$70

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Villa Donna

Ironshore b and b

7 bedrooms / 7 bathrooms / sleeps 28

Responds fast! avg. 2 hours 56 minutes

Price per night from

$490

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Luxury 2 bedroom suite with living area and balcony 900 SQF - Palm Suite

Montego Bay apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 3 minutes

Price per night from

$150

1 / 50

Ocean view 2 BR, 2 1/2 Bath inc. staff

Montego Bay house

2 bedrooms / 3 bathrooms / sleeps 5

“Treated like King and Queen!!!” My wife and I arranged to stay in this condo for our honeymoon in Montego Bay, Jamaica for 10 days in December '13. This condo came highly recommended from friends of ours that vacationed there. Our host, Jennifer alt

Responds fast! avg. 1 hour 42 minutes

Price per night from

$175

1 / 24

Avalon - Tryall Club

Hopewell villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$714

1 / 17

Casa Bella Villa

Rose Hall villa

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 3 hours 52 minutes

Price per night from

$700

1 / 25

Mobay Club Studio Hip Strip, Beach Pool Nightlife

St James, Montego Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 19 minutes

Price per night from

$95

1 / 34

Ocean View Retreat

Ironshore villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$290

1 / 19

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 1 hour 34 minutes

Price per night from

$623

1 / 24

Karma Bay - Tryall Club

Hopewell villa

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,143

1 / 14

Pleasant View Villa

Hopewell house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 43 minutes

Price per night from

$278

1 / 20

GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS

Ironshore house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,429

1 / 44

TWIN PALMS RETREAT - MONTEGO BAY JAMAICA

Montego Bay townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

Price per night from

$360

1 / 47

Luxury 1 bedroom suite with balcony 500 SQF - Cotton Suite

Montego Bay villa

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 3 minutes

Price per night from

$120

1 / 50

Gemini 3 Bedroom Villa

Ironshore cottage

3 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 2 hours 56 minutes

Price per night from

$255

1 / 17

2 bed/ 2.5 bath Ocean Front Condo Montego Bay Club

Montego Bay condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 19 minutes

Price per night from

$189

1 / 29

Enjoy True Jamaican Hospitality at Davelyn Villa

Montego Bay villa

4 bedrooms / 5 bathrooms / sleeps 8

“Awesome Visit to Montego Bay!” Visited this villa in June 2015 for a girls trip. The villa is nice and staff was awesome. Ms. Kesha was very sweet and she is an awesome cook! It was 6 of us and we occupied 3 of the 4 rooms. The house was very cle

Price per night from

$142

1 / 14

Sundance - Tryall Club

Hopewell villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,949

1 / 13

2 Bedrooms 2 Bath New Luxury Ocean Front Condo

Montego Bay condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$169

1 / 43

Island House - Tryall Club

Hopewell villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$643

1 / 17

Jus' Beachy - Luxury Apartment in Beachfront Gated Community

Montego Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 30 minutes

Price per night from

$169

1 / 26

Infinity - Tryall Club

Hopewell villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$2,091

1 / 17

Seaview Chateau

Ironshore house

9 bedrooms / 9 bathrooms / sleeps 18

Responds fast! avg. 2 hours 56 minutes

Price per night from

$1,200

1 / 35

Overlook - Tryall Club

Hopewell villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,558

1 / 15

Butler Service! Chef! Pool! Elegant! Caribbean Jewel

Rose Hall villa

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$857

1 / 47
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