Vacation Rentals & Condos in Cayman Islands

Updating...

age 0-16
300 Results

Relevance

Price: low to high

Price: high to low

Reviews

300 condos

JAMAICA HILLTOP PARADISE (YOUR CASTLE AWAITS YOU)

Runaway Bay house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$1,239

VILLA MARA

Mammee Bay villa

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 19

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$3,438

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$800

Eslyn Villa Runaway Bay - A Home Away From Home...

Runaway Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$196

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: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$822

2 Bedroom Luxury Sea View Villa

Ironshore villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$343

4 Bedroom Luxury Sea View Villa

Ironshore villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$628

Jetaway Montego Bay (Entire Villa)

Ironshore villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 25

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$2,512

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!

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$1,605

6 Bedroom Luxury Sea View Villa

Ironshore villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$914

Sunspot Spot Villa - Charming 6 Bedroom Beach Front Villa Jamaica

Runaway Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$2,741

Tennsville

Ironshore villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$320

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

Ironshore villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 21

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$2,855

Beautiful New & Private Villa-- Centrally Located In Runaway Bay, Jamaica W.I.

Runaway Bay villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$543

Villa Turrasann

Runaway Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$659

Reef Winds Villa

Runaway Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 28 minutes

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$371

Ma Moura

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$2,644

Poinciana

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$836

Villa Amana (up to 20 persons)

Hopewell villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 24

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$5,258

Hummingbird House (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,374

Love and Livity (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,063

Sugar Magnolia

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$2,715

Following Seas (up to 10 persons)

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,374

Villa Amana (up to 16 persons)

Montego Bay villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,510

Ambiance Sea Salt (up to 10 persons)

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$3,297

Love and Livity (up to 8 persons)

Hopewell villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$3,643

Dragon Fly - Your Unique Beach View Paradise

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,045

Bee Happy

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$1,024

Hummingbird House (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,835

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$172

Hummingbird House (up to 14 persons)

Montego Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$5,285

Little Palm

Hopewell villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$941

Following Seas (up to 12 persons)

Montego Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$4,825

Bali Hai

Hopewell villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$2,403

Love and Livity (up to 6 persons)

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$1,929

No Problem

Hopewell villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$1,266

Ambiance Sea Salt (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$3,956

Villa Amana (up to 12 persons)

Hopewell villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$3,344

Viewing 38 of 300
rentals in Cayman Islands

×

Also consider