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Houses in Cayman Islands and Villas - Holiday Lettings - Holiday Rentals Cayman Islands

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269 Holiday homes

Rum Point holiday home rental

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

from £380 / night

£2,656 / week

Rum Point holiday home rental

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

1

from £496 / night

£3,466 / week

Holiday guest house in Seven Mile Beach

Seven Mile Beach guest house

2 bedrooms / 2 bathrooms / sleeps 6

11

from £166 / night

£992 - £2,158 / week

Home rental in Cayman Islands with shared pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

from £378 / night

£2,642 / week

Holiday condo with shared pool in Cayman Islands

Seven Mile Beach condo

4 bedrooms / 5 bathrooms / sleeps 10

14

Responds fast! avg. 3 hours 6 minutes

from £873 / night

£6,111 - £18,936 / week

Holiday villa with shared pool in Rum Point

Rum Point villa

3 bedrooms / 3 bathrooms / sleeps 8

1

from £496 / night

£3,466 / week

Holiday home in Cayman Islands

Cayman Brac house

2 bedrooms / 2 bathrooms / sleeps 5

2

from £125 / night

£748 - £864 / week

Holiday home with shared pool in Cayman Islands

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

from £381 / night

£2,668 / week

Holiday apartment in Cayman Islands

Bodden Town apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

from £83 / night

£576 / week

Holiday home in Bodden Town

Bodden Town house

2 bedrooms / 2 bathrooms / sleeps 4

from £83 / night

£576 / week

Holiday apartment in Cayman Islands

Bodden Town apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £95 / night

£659 / week

Holiday apartment in Cayman Islands

Breakers apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 3 hours 3 minutes

from £75 / night

£524 / week

Holiday villa rental

Seven Mile Beach villa

2 bedrooms / 2 bathrooms / sleeps 4

2

from £1,795 / night

£12,564 - £20,102 / week

Holiday villa with shared pool in Seven Mile Beach

Seven Mile Beach villa

4 bedrooms / 3 bathrooms / sleeps 10

from £942 / night

£6,588 / week

Holiday apartment with shared pool in Rum Point

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Excellent Cayman Kai Condo” We've stayed in the Kaibo Phase II condos several times previously and Moonlight Kai did not disappoint. Maia was really easy to work with in setting everything up. We had one slight issue with the payment (nothing to do with Maia) which was easily cleared up with a quick visit to the rental management office two minutes away. The furnishings are very modern, the kitchen was equipped with everything we needed and having Kaibo right next door cannot be beat. All in all, if you're looking for the quieter side of Cayman but still close to the essentials then this condo will suit you perfectly. We'd definitely rent this unit again.

41

from £185 / night

£1,295 / week

Holiday home in Cayman Islands

East End house

2 bedrooms / 2 bathrooms / sleeps 6

“Paradise in the Caymans” If your idea of vacation is relaxing on a beach away from the maddening crowds then this is the place. This totally accessible cottage steps from a private beach was an amazing find. Newly remodeled with a gorgeous decor, comfortable beds, dishwasher, washer and dryer and walk-in shower, our every need was met. Cathy and Jerry made sure we felt right at home. The house was nicely stocked with towels, soap, shampoo and laundry detergent. A car is a must if you want to explore and driving was easy on the East End. I wish we had stayed two weeks!

20

Responds fast! avg. 3 hours 15 minutes

from £207 / night

£1,237 - £1,856 / week

Cayman Islands holiday apartment rental

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

11

from £246 / night

£1,721 / week

Cayman Islands holiday home rental

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 12

1

Responds fast! avg. 3 hours 15 minutes

from £639 / night

£3,835 - £6,680 / week

Holiday home in Rum Point

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 3 hours 15 minutes

from £330 / night

£1,979 - £3,093 / week

Holiday home in Cayman Islands

Little Cayman house

3 bedrooms / 3 bathrooms / sleeps 7

1

from £659 / night

£4,612 / week

Holiday apartment with shared pool in Cayman Islands

West Bay apartment

1 bedroom / 1 bathroom / sleeps 4

16

from £189 / night

£1,320 / week

Holiday home in North Side

North Side house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 15 minutes

from £326 / night

£1,955 - £2,944 / week

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

5

Responds fast! avg. 3 hours 58 minutes

from £226 / night

£1,583 / week

Rum Point holiday apartment rental

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

3

from £165 / night

£1,151 / week

Holiday villa accommodation

Cayman Brac villa

2 bedrooms / 2 bathrooms / sleeps 4

2

Responds fast! avg. 3 hours 8 minutes

from £148 / night

£988 - £1,160 / week

Holiday apartment with swimming pool in Cayman Islands

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Absolutely amazing!” We recently had the pleasure of staying for 9 nights in the Mid-Winter Night's Dream condo on the north side of Grand Cayman. It was absolutely amazing! Dan was very easy to deal with, provided us a lot of tips and information about Grand Cayman and it was just a great experience. Everything we could possibly need was right there at the condo. We ate quite a few meals there and they had everything we needed to cook and grill. It was super clean and bright. View of the ocean right outside the master bedroom couldn't be beat...going to sleep with the sounds of the waves hitting the shore made for some amazing full night's sleep. Breakfast out on the lanai every morning. The pool was great! It felt wonderful after a day of snorkeling or just a first thing in the morning dip. Having the ocean right out our door was pretty amazing also. Snorkeling right there when the water was a little less wavy led to some nice adventures. They even have the snorkel gear and coolers for you for all day adventures! Being on the north side gave us a great opportunity to be away from the noise and commercialism of Seven Mile Beach and truly let the sun soak into our bones and relax. We still were only a 45 min drive to that side when we wanted to be. And it's only that long because you have to drive 30mph a lot of the way...which gives you time to really look around and admire the view! Definitely rent a car, there is plenty of space at the condo and it will afford you the opportunity to get to all the different parts of the island to check out all the amazing snorkeling spots. I will definitely stay here again!! You couldn't ask for more!

28

from £183 / night

£1,279 - £1,861 / week

Cayman Brac holiday villa rental

Cayman Brac villa

3 bedrooms / 5 bathrooms / sleeps 8

8

Responds fast! avg. 28 minutes

from £289 / night

£2,288 - £2,867 / week

Cayman Islands holiday cottage rental

Cayman Brac cottage

1 bedroom / 1 bathroom / sleeps 3

“Back to the Brac” We loved our time at Cayman Cottage on the Brac! This was our second trip to the Cottage and it was as wonderful as we remembered! The cottage has its own private, gorgeous beach that we drank coffee on early in the morning, snorkeled and sunned on in the afternoons and watched the beautiful sunsets each evening! It is clean, well maintained and comfortable. The owner is friendly and pleasant, accommodating any requests or questions we had. We walked to one of three nice restaurants most evenings, for delicious seafood or local island specialties. The island is very safe and the local people are friendly. We walked the island exploring each day and never had a minute of apprehension. We highly recommend Cayman Cottage for your taste of Paradise!

28

from £135 / night

£940 / week

Holiday villa in Cayman Islands

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

5

Responds fast! avg. 52 minutes

from £164 / night

£1,142 / week

Holiday apartment in Cayman Islands

Cayman Brac apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Charming seaside cottage” Excellent location for the best snorkeling on island, quiet,private and on very low use back road perfect for morning and evening walks.(watch for the night herons) Rental is clean,owner truly a pleasure to work with. Safe area, close to fascinating museum and grocery store. Rates best on island.

5

from £126 / night

£878 / week

Holiday apartment in Cayman Islands

West Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

15

Responds fast! avg. 56 minutes

from £330 / night

£2,142 / week

Holiday villa in Cayman Islands

North Side villa

3 bedrooms / 2 bathrooms / sleeps 6

“Escape from Brutal Chicago Winter - Vacation in Paridise” This is a very well maintained property with comfortable, up-to-date furnishings. The view is fantastic, and just as pictured. Plenty of dinnerware and cookware were provided, as well. We spent most of our time between Rum Point and at this lovely villa...just lounging, reading and enjoying the wonderful Caribbean sun. If you are looking for "action" on a daily basis this may not be your place, but if you value a knock-out view, relaxation, and privacy, this villa on the "quiet" side of the island is perfect. One trip to 7 Mile Beach and Georgetown was all we needed and were grateful to get back to real island living. Frank is easy to work with and quick to respond to questions and comments. Tukka, Lighthouse, Kaibo, and Over the Edge restaurants are nearby as well as dining at Rum Point. All very good. A small grocery store called Chisholm's is a few minutes away for everyday items. Fosters Express on the east end about 10 minutes away is also handy. For more serious shopping, Hurleys and a larger Foster's are about 30 minutes away. They stock everything you might get in the us. All in all...after a brutal winter here in the Chicago area, this was a slice of heaven. I would not hesitate to recommend this villa. Thank you Frank and Del for sharing!

21

from £329 / night

£2,208 - £3,374 / week

Holiday apartment in Cayman Brac

Cayman Brac apartment

1 bedroom / 1 bathroom / sleeps 2

7

from £108 / night

£751 / week

Holiday home with shared pool in Cayman Islands

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

“Simple pleasures in an amazing setting.” Dear Janice and Mike We're writing this email to let you know how much we enjoyed our visit to Starboard Kai at the beginning of May. You have refurbished the house beautifully - you must be very proud of it. It certainly is very easy 'island living.' It was immaculately clean with high quality towels/linens. The wi-fi was fast and dependable.The master bed must be the most comfortable on Grand Cayman. Outside, the pool and grounds are conscientiously maintained to a high level. We loved the position of the house just across from Rum Point but we were never disturbed by noise from the road or 'over the road'. There are lots of things to keep you busy as have been detailed by the other reviews here. Our favourites were a) cycling down to Starfish Point each day for an early morning swim when there's no-one else about and b) taking a few steps across the road to the Rum Point Wreck Bar at around 6pm, buying a Rum Point Sunset (cocktail) and sitting in the peace and quiet watching the sun go down. Simple pleasures........ Your house manager Mitzie was off the island at the time of our visit but Sharon popped by on the first morning to see if we were OK. As it happened, just as she came by, we were struggling (and failing!) to pump up the rear tyres of both the bikes which had been left deflated by previous tenants. They needed more work on them than just the pump so Sharon took them away to have them fixed but managed to source two bikes for us from elsewhere. What wonderful service. Please pass on our thanks to her if you see her. Our week passed by very quickly with no further problems and we were sorry to leave. We would have no hesitation in recommending Starboard Kai to others. Helen and Chris (UK)

26

from £329 / night

£2,302 / week

Villa accommodation in Cayman Islands

West End villa

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 1 hour 13 minutes

from £119 / night

£832 / week

Home rental in Cayman Islands

Old Man Bay house

4 bedrooms / 5 bathrooms / sleeps 8

“The best of the best!!!” Just what we needed! A beautiful home, perfect location to calm our tired souls and mend our weary bodies and every amenity and convenience you could possibly ask for. Villa Caymanas is truly a dream come true, a private paradise on a "grand" little island. We have had the time of our lives. No where could have been as perfect as Villa Caymanas. The owners have thought of everything... We have had so much fun; will never forget and hope to return very soon to Villa Caymanas.

14

Responds fast! avg. 3 hours 15 minutes

from £454 / night

£2,722 - £4,330 / week

Holiday home in Cayman Islands

Rum Point house

5 bedrooms / 4 bathrooms / sleeps 10

“Perfect family getaway...!” We stayed at Cayman - Rum Point two years ago in a different villa...just as beautiful but incredibly windy. Two Rainbows is tucked away around the bend and it made all the difference in the world. We enjoyed our private beach without the bothersome wind. We are two families, with 5 kids under the age of 12, and we had the beach right at our own back door, without having to walk down a walkway, shallow smooth water, walking distance to Rum Points restaurant/bars/shops. We could sit on the back porch and watch the kids play - unlike others where the porch is elevated and you do not have a clear view of the beach. The villa accommodated us perfectly. Our best spring break trip yet...!

5

Responds fast! avg. 3 hours 15 minutes

from £825 / night

£4,948 - £8,411 / week

Holiday apartment with shared pool in Seven Mile Beach

Seven Mile Beach apartment

4 bedrooms / 5 bathrooms / sleeps 10

5

from £2,471 / night

£17,297 / week

Holiday guest house in Spot Bay

Spot Bay guest house

2 bedrooms / 1 bathroom / sleeps 4

1

from £106 / night

£632 / week

Holiday apartment with shared pool in George Town

George Town apartment

2 bedrooms / 2 bathrooms / sleeps 5

1

Responds fast! avg. 3 hours 7 minutes

from £278 / night

£1,944 / week

Viewing 40 of 269
rentals in Cayman Islands

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Cayman Islands holidays

The Cayman Islands are a British protectorate and are considered one of the most exclusive destinations in the Caribbean. Famous for their stunning natural beauty, the Cayman Islands have a tropical marine climate, making for warm and rainy summers and dry, mild winters. Most visitors elect to come here between October and April to escape the cold weather of the northern climates and take advantage of the Caymans' celebrated beauty.

Some of the major attractions and activities in the Cayman Islands include:

  • The Sister Islands: While Grand Cayman dominates most visitors' itineraries, the so-called "Sister Islands" of Little Cayman and Cayman Brac are perfect for those seeking a quieter, more private holiday.
  • George Town: The islands' capital city, George Town has an engaging and fascinating history, and it is well worth taking a tour of the city's many sights and points of interest.
  • Seven Mile Beach: Located on Grand Cayman, Seven Mile Beach is one of the most-developed corners of the Cayman Islands. Stroll the boardwalks, relax at a beachfront bar and take advantage of the excellent restaurants and lively nightlife. This area is the perfect setting for Cayman Islands weddings and Cayman Islands honeymoons.
  • Deep-sea diving: With crystal clear waters and mysterious coral reefs, the Cayman Islands offer some of the best scuba diving in the world. Diving enthusiasts from all over the globe come here in search of the ultimate experience.
  • Golf: Cayman Islands golf courses rank amongst the best in the Caribbean, and the weather is always perfect for teeing off. Club and equipment rentals are widely available and affordable, so you don't have to worry about lugging along your own gear.

Instead of cramping into a hotel room, relax in style in your very own holiday rental. A beachfront villa, a condo in George Town or an apartment on the coast makes the ideal alternative to traditional accommodations at affordable prices.

The islands lie less than 100 miles to the south of Cuba, and are also perfectly situated to continue your journey in Puerto Rico. As a popular port of call, it's also easy to get from the Cayman Islands to the U.S. and British Virgin Islands and many other Caribbean nations.

Top Destination reviews

Great Location & Value! 7mile Beach Condo next to *NEW* Margaritaville Resort
Very good stay - Livia was very attentive and full of suggestions of places to eat/go

On 7 Mile beach - I loved the early morning walks and later afternoon walks along one of the most beautiful beaches. Apartment was good with plenty of space and facilities … see more
2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2
Fantastic apartment

Very comfortable and well equipped apartment. Plenty of space. Balcony was meshed so no problems with insects. The recently upgraded white goods make this apartment even better. Lovely location in a quieter part of the island but still easy to access. Kayak and bikes were an added bonus. The proximity to starfish point, Rum Point and the bio bay make vista easy. The yacht club restaurant and bar next door offered a good selection of food and drink- the Tuesday evening bbq worth a visit. The only disappointment was the beach/sea in the bay is not really for swimming due to jelly fish, boat traffic and the ‘lagoon smell’ - this isn’t the open sea. Thankfully the lovely swimming pool made up for this. Had a fantastic holiday and would love to return.see more
Caribbean Club - 2 Bedroom Villa at Seven Mile Beach - Book Now
We couldn't have been happier

This was our first time to stay at the Caribbean Club. The location is amazing and the beach was an absolute dream. We loved it and cannot recommend it highly enough. Thank you Exceptional Villas for the recommendation. … see more
Villa Emmanuel
Wonderful experience!

Villa Emmanuel was perfect for us!! We stayed for two weeks and everyone loved it! The house, pool and oven were amazing. Villa Emmanuel is away from the busy area of Grand Cayman, but we could walk to either Kaibo or Rum Point for a restaurant or quaint entertainment. (You do need a car to get groceries) My kids, my mother, my husband, my friends and I all had a very relaxing memorable experience! I was sad to leave. see more

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