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Villas in Grand Cayman and Holiday rentals - Holiday Lettings - Holiday Rentals Grand Cayman

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190 Holiday homes

George Town holiday condo rental

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

from £90 / night

£631 / week

1 / 10

Holiday apartment with swimming pool in North Side

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect Family Vacation” Dan was a pleasure to rent from. He responds quickly to questions and the description of the condo in the ad is accurate. We had plenty of room for the four of us (two adults, two teenage girls) and the condo is stocked with everything you will need. We opted to leave our swim fins home to save room, as there are several pairs in the condo to use. The north end is quiet and more remote than the west end of the island...which is just what we wanted. Excellent snorkeling right out front and many, many other cool public beaches to check out within a 10-15 minute drive away. We will definitely rent from Dan again.

from £223 / night

£1,557 - £2,192 / week

1 / 21

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £3,116 / night

£21,812 / week

1 / 7

Holiday apartment with golf nearby in Seven Mile Beach

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £304 / night

£1,906 - £2,605 / week

1 / 47

Holiday home in North Side

North Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £477 / night

£3,335 / week

1 / 24

Holiday home in East End

East End house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £540 / night

£3,780 / week

1 / 22

Holiday home in North Side

North Side house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £385 / night

£2,692 / week

1 / 12

North Side holiday apartment rental

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Everything we needed” The condo was clean and well equipped with thoughtful extras like beach bags, umbrellas, and a cooler. We really enjoyed the lanai (screened in porch) with table and chairs. The outdoor furniture was comfortable. Both overlooking the ocean. We have stayed in over a dozen condos throughout the Caribbean, and this was the best. We would stay there again. Excellent experience.

from £205 / night

£2,319 - £2,446 / week

1 / 11

Holiday villa with shared pool in Bodden Town

Bodden Town villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £181 / night

£1,262 / week

1 / 26

Home accommodation in West Bay

West Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £991 / night

£6,937 / week

1 / 20

Holiday home in Rum Point

Rum Point house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 20

from £5,309 / night

£37,161 / week

1 / 51

Holiday home in North Side

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £359 / night

£2,510 / week

1 / 21

Holiday home in Rum Point

Rum Point house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £722 / night

£5,050 / week

1 / 35

West Bay holiday condo rental

West Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £340 / night

£2,376 / week

1 / 24

Old Man Bay holiday home rental

Old Man Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

“Wonderful time in the Caymans” Over all the house was great. There were two things that we were disappointed in. The pool was never warm enough to use and even whenwe called was not fixed. The beach was so full of trash and the water was so rough we had to go to Rum Point or the other side of the island to enjoy it.

from £722 / night

£5,050 / week

1 / 38

Rum Point holiday home rental

Rum Point house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £1,482 / night

£10,373 / week

1 / 27

Rum Point holiday home rental

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £747 / night

£5,226 / week

1 / 40

Holiday home in North Side

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £359 / night

£2,510 / week

1 / 29

Gun Bay holiday home rental

Gun Bay house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £1,039 / night

£7,274 / week

1 / 36

Holiday home rental

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Beautiful location but local management is poor” We enjoyed the house and location very much. It is in a wonderful exclusive part of the island and the house has a very relaxed vibe about it. It is fantastic to be able to swim, or snorkel directly from your own beach. A few things around the house need some attention. For example, 2 of the aC units did not work at all and we had to deal with workmen in the house all day Monday. This should be taken care of beforehand - not on our holiday time. The workmen left bits of copper piping, drywall, all sorts of stuff over both beds and floor - also left a lot of their gear on the front lawn, which did not move our entire trip. Not great. House keys were nowhere to be found when we arrived, not only did Mitzi not "pop by" the first day to say hi - she stomped into the house unannounced one morning with a man to " check something out". Actually she never introduced herself so I am guessing it was her. I tried to speak with her about a few things, but she wasn't interested and had a pretty bad attitude. Other things were minor, but the kitchen needs to be stocked better, a corkscrew that works for example and more stemware. Pink towels in front master bedroom should be thrown away - threadbare and discolored, same with white blanket on bed - holes and frayed. I stayed at a small one bedroom cottage on Little Cayman the next week and the local management rocked-and the cottage was in amazing shape. I should mention that my dealings with Jim Leavitt were always excellent and he provided us with lots of great information that we used while we were there.

from £631 / night

£4,415 / week

1 / 22

Home rental in Old Man Bay

Old Man Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Wonderful 5 star Villa!” We recently spent 10 days at Villa Caymanas for Spring Break. We found this to be the perfect home for our stay on Grand Cayman with extended family. The house and grounds are immaculately cared for. The layout and suites were perfect for our teen children, in-laws and daughter/son-in law (group of 8). They allowed privacy and were very clean and comfortable. We used the outdoor gas grill and cooked meals for our large group and found the kitchen to be well stocked with all of the necessary gadgets to do so. The location is peaceful and private and was the perfect setting for a vow renewal which took place oceanfront at sunset. We enjoyed the ocean kayaks several days, the waters were very calm during our stay. I particularly enjoyed the shaded hammocks and several outdoor gathering areas. My daughters also enjoyed working out in the home gym, riding the bicycles and swimming in the pool. We also enjoyed beach time at Rum Point and Starfish Point which were both only a short drive from the house. We found that we prefer the Northside of Grand Cayman - away from the hustle and bustle of the cruise ship traffic. We found several wonderful restaurants just minutes from the house. Overall, this property is very spacious, private and well cared for with a beautiful oceanfront setting.

from £500 / night

£3,494 / week

1 / 29

Holiday home rental

West Bay house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £454 / night

£3,177 / week

1 / 20

Holiday home in Savannah

Savannah house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from £901 / night

£6,306 / week

1 / 39

Holiday home in Rum Point

Rum Point house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Awesome house - Outdoor living area is amazing” This house is amazing. Every room is comfortable. The master suite is gorgeous and spacious. The pool area is fantastic and all the outdoor furniture is comfortable. We lounged by the pool every afternoon while our little one napped. The walk to Rum Point Beach was easy and the beach was fun. We enjoyed being on this side of the island and could not have asked for a better house!

from £720 / night

£5,036 / week

1 / 38

Holiday home letting

Rum Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £448 / night

£3,136 / week

1 / 22

Apartment rental in West Bay with shared pool

West Bay apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,801 / night

£12,605 / week

1 / 55

West Bay holiday apartment rental

West Bay apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,809 / night

£12,661 / week

1 / 53

Holiday villa in Seven Mile Beach

Seven Mile Beach villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £1,086 / night

£7,601 / week

1 / 15

Bodden Town holiday villa rental

Bodden Town villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,032 / night

£7,220 / week

1 / 35

Holiday home in Rum Point

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £313 / night

£2,185 / week

1 / 21

Holiday apartment in Bodden Town

Bodden Town apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £114 / night

£1,089 / week

1 / 15

Holiday home in Rum Point

Rum Point house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £266 / night

£1,861 / week

1 / 19

Holiday home rental

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £359 / night

£2,510 / week

1 / 26

Condo rental in West Bay

West Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £340 / night

£2,376 / week

1 / 27

Holiday home in George Town

George Town house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

from £720 / night

£5,036 / week

1 / 36

Holiday home in East End

East End house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Home for the holidays!” My best friend and I had the ultimate pleasure of staying at the Sea Beauty for 7 days. It was the most wonderful vacation I have ever had. Ironically, I lived in Grand Cayman for two years from 1997-99 and, at that time, I rented and lived in the Sea Beauty. Coming back was just like coming home again! Cathy and Jerry Frazier are two of the kindest people I could ever hope to meet and they were wonderful hosts. The cottage itself was comfortable, exceptionally clean and located across from a beautiful private beach on Frank Sound. The proximaty of the cottage to other beaches was wonderful as well. Away from the hustle and bustle of George Town we enjoyed a peaceful and relaxing vacation. I would recommend the Sea Beauty for anyone looking to relax away from the more tourist oriented parts of Grand Cayman. At the Sea Beauty you truly feel like a part of the island life. Frank Sound is gorgeous and you are just minutes away from Rum Point and Morritts Tortuga Club. I was so relaxed and happy every minute of my stay.I hope to have the opportunity to stay at the Sea Beauty again someday. Special thanks to Cathy and Jerry Frazier and Jim Leavitt.

from £227 / night

£1,584 / week

1 / 30

Holiday home rental

Rum Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £539 / night

£3,769 / week

1 / 25

Holiday condo in Old Man Bay

Old Man Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £266 / night

£1,861 / week

1 / 24

Holiday home in Gun Bay

Gun Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £1,131 / night

£7,917 / week

1 / 35

Rum Point holiday home rental

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £258 / night

£1,805 / week

1 / 25

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Grand Cayman holidays

Grand Cayman, Little Cayman, and Cayman Brac are the three sister islands that make up the British Overseas Territory of the Cayman Islands. Best known for its slow easy pace of life and its natural beauty, the area of Grand Cayman certainly offers the paradise you've seen in the movies. When you first arrive here, get settled in your holiday rental and then head for the long stretch of soft white sand and calm blue water known as Seven Mile Beach. Take out a rental boat, go scuba diving, or just relax. And when you're ready to get away from the beach, head into the heart of George Town for an unforgettable dining experience.

Here are a few additional suggestions of things to do in Grand Cayman:

  • Diving: Grand Cayman offers some of the best diving opportunities in the Caribbean. For real adventure, go wreck diving from Cayman Brac or explore the Blood Bay Wall on Little Cayman.
  • Parasailing: Get a spectacular view of Grand Cayman from the sky above Seven Mile beach.
  • Surfing and snorkelling: These are just a few of the water sports you can sample on Seven Mile Beach. Equipment rentals are easy to find, or you can bring your own board, fins, snorkel, and mask.
  • Stingray City: You won't believe descriptions of the stingrays here until you see them. Enormous and gentle, fearless and bizarre, the creatures of Grand Cayman's best known attraction will eat squid right out of your hand as you snorkel amongst them.
  • Hiking and bird watching on Cayman Brac and Little Cayman: Hike the trails of the two smaller islands and take a pair of binoculars and a camera to capture your encounters with remarkable bird and iguana species.

Come to the Cayman Islands in November for the legendary Pirate Festival, or time your visit to run the Cayman Island Marathon or take part in the Cayman's Jazz fest. No matter when you arrive here, the local people will give you a warm welcome that will make you want to stay forever.

It's easy to move between the three islands, and getting around in George Town should present no problems since you can walk almost anywhere. Find a villa rental for the entire holiday season to see how Grand Cayman celebrates or find a condo near the beach and stay a week or two in the summer.

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