Villas Cayman Islands

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361 villas

Windfall Villas... FREE TRANSPORTATION !

St James, Montego Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

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Price per night from

$345

Celebrity Villa Jamaica

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 18

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Price per night from

$1,323

Beverly Hills Villa

Runaway Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$89

Sea View Queen Room in Luxury Villa

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$248

"Home Sweet Home" - - Pool/Gym/Clubhouse/Cafe

Ocho Rios villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$138

Jamaican Styles Villa

Saint James Parish villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 10

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$81

Twin Room in Luxury Villa (1 of 2)

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$110

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

$825

Deluxe Queen Room in Luxury Villa

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$236

2 Bedroom Luxury Sea View Villa

Ironshore villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$345

Sea View Double Room in Luxury Villa (2 of 2)

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$225

Sea View Double Room in Luxury Villa (1 of 2)

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$225

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$288

4 Bedroom Luxury Sea View Villa

Ironshore villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$633

Jetaway Montego Bay (Entire Villa)

Ironshore villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 25

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Price per night from

$2,530

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Price per night from

$299

6 Bedroom Luxury Sea View Villa

Ironshore villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$920

Twin Room in Luxury Villa (2 of 2)

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$196

Pink Hibiscus Villa - Private Pool

Ironshore villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 18

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Price per night from

$1,150

Hatfield South Villa

Ironshore villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$978

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

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 21

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Price per night from

$2,875

Hithatcher Escape Villa your perfect luxurious Jamaican holiday location!!!

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$173

Casa Marina on the Bay/Beach

Montego Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 54 minutes

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Price per night from

$91

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

Blue Heaven Villa

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,150

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

$271

Birdhouse Music Mansion by Temple X (Guest Villa)

Rose Hall villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$573

Crystaljamaica Villa Tours and airport transfer

Ironshore villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 16

Responds fast! avg. 31 minutes

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Price per night from

$960

The Paradise by TRVLR

Ironshore villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$745

A home away from home

St. Ann's Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

Beach/Pool/Sun/fun/family /6 bedroom get away.

Runaway Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 24

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Price per night from

$432

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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

Villa Windy Way

Ironshore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

256 Jamaica

Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$81

Topaz Dream Palace - live-in hosts - can book separate rooms

Montego Bay b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

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Price per night from

$41

Home Sweet Home

Montego Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$92

Sundown Beach Studio

Montego Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$156

Authentic Jamaican Home

Salem house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$69

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rentals in Cayman Islands

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