COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

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

Updating

age 0-16
306 Results

Relevance

Price low to high

Price high to low

Reviews

306 Holiday homes

Rum Point holiday home rental

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 11 minutes

from £244 / night

£1,707 / week

Rum Point holiday home rental

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

1

Responds fast! avg. 3 hours 11 minutes

from £282 / night

£1,970 / week

Holiday guest house in Seven Mile Beach

Seven Mile Beach guest house

2 bedrooms / 2 bathrooms / sleeps 6

11

from £184 / night

£1,125 - £2,448 / week

Home rental in Cayman Islands with shared pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 11 minutes

from £282 / night

£1,970 / 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 9 minutes

from £978 / night

£6,841 - £20,899 / week

Holiday villa with shared pool in Rum Point

Rum Point villa

3 bedrooms / 3 bathrooms / sleeps 8

1

Responds fast! avg. 3 hours 11 minutes

from £282 / night

£1,970 / week

Holiday home in Cayman Islands

Cayman Brac house

2 bedrooms / 2 bathrooms / sleeps 5

2

from £141 / night

£846 - £977 / week

Holiday home with shared pool in Cayman Islands

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 11 minutes

from £244 / night

£1,707 / week

Holiday villa in Cayman Islands

Seven Mile Beach villa

4 bedrooms / 4 bathrooms / sleeps 8

1

from £1,114 / night

£7,797 - £16,842 / week

Holiday apartment in Cayman Islands

Bodden Town apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

from £95 / night

£659 / week

Holiday home in Bodden Town

Bodden Town house

2 bedrooms / 2 bathrooms / sleeps 4

from £95 / night

£659 / 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

from £85 / night

£593 / week

Holiday villa rental

Seven Mile Beach villa

2 bedrooms / 2 bathrooms / sleeps 4

2

from £724 / night

£5,068 - £12,527 / 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 villa in Seven Mile Beach

Seven Mile Beach villa

3 bedrooms / 3 bathrooms / sleeps 7

4

from £1,261 / night

£8,826 - £22,776 / 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 £178 / night

£1,476 / 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 21 minutes

from £210 / night

£1,467 / week

Cayman Islands holiday apartment rental

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

11

Responds fast! avg. 1 hour 0 minutes

from £282 / night

£1,970 / week

Cayman Islands holiday home rental

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 12

1

Responds fast! avg. 3 hours 21 minutes

from £694 / night

£4,857 / week

Holiday home letting

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 10

“Honeymoon” I spent two weeks in Grand Caymen on my honeymoon... The first at the ritz and the second at this remarkable property fit for royalty. I'll start by saying the house is insane with a private pool and hot tub. The inside of the house is extremely comfortable with all the comforts of home. The land the house sits on is very secluded and views of the ocean are ridiculous. My wife and I started everyday with morning yoga overlooking the ocean. We finished every night with a romantic hot tub looking at the stars. One of my favorite things about this house is I could swim out to the reef which took no more then 5 minutes and have insane snorkeling. There was plenty of other things to do in the area... Jet skiing and beach within a 5 minute drive. We had a car and driving into town when we wanted to go out to dinner was no problem. The owner was very knowledgable about the island and pointed us to all the best local restaurants. This is by far the most beautiful part of the island and would recommend this home for a romantic getaway or a family vacation. I can't wait to get back!!!

17

Responds fast! avg. 5 minutes

from £615 / night

£4,303 / week

Cayman Islands holiday condo rental

George Town condo

2 bedrooms / 2 bathrooms / sleeps 6

3

Responds fast! avg. 8 minutes

from £353 / night

£2,467 / week

Holiday home in Rum Point

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 3 hours 21 minutes

from £350 / night

£2,445 / 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

£1,318 / week

Holiday home in North Side

North Side house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 21 minutes

from £275 / night

£1,924 / week

Holiday home rental

Gun Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

from £443 / night

£3,097 / week

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

5

from £330 / night

£2,306 / week

Rum Point holiday apartment rental

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

3

from £179 / night

£1,250 / week

Holiday villa accommodation

Cayman Brac villa

2 bedrooms / 2 bathrooms / sleeps 4

2

from £170 / night

£1,130 - £1,328 / 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 £207 / night

£1,450 - £2,109 / week

Cayman Brac holiday villa rental

Cayman Brac villa

3 bedrooms / 5 bathrooms / sleeps 8

8

Responds fast! avg. 24 minutes

from £329 / night

£2,603 - £3,261 / week

Cayman Islands holiday home rental

Cayman Brac house

2 bedrooms / 1 bathroom / sleeps 4

3

from £141 / night

£987 / week

Seven Mile Beach holiday apartment rental

Seven Mile Beach apartment

3 bedrooms / 3 bathrooms / sleeps 6

9

from £226 / night

£1,186 / 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 £141 / night

£987 / week

Holiday villa in Cayman Islands

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

5

Responds fast! avg. 2 hours 2 minutes

from £188 / night

£1,316 / 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 £142 / night

£989 / 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 £316 / night

£2,118 - £3,295 / week

Holiday apartment in Cayman Brac

Cayman Brac apartment

1 bedroom / 1 bathroom / sleeps 2

7

from £122 / night

£849 / week

Viewing 40 of 306
rentals in Cayman Islands

×

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

*BEST RATE GUARANTEED-PLEASE ENQUIRE*Luxury 3 Bedroom Villas on Seven Mile Beach
We loved every minute

We had the best week at the Caribbean Club. Everything was incredible - from the service we received from Noreen and Emma at Exceptional Villas to the service we received during our stay at the Caribbean Club. We could not fault a thing! The amenities were superb… The beach attendant was always there with lounge covers, drinks, or available for paddle board rentals, etc. Room service was excellent and efficient. The gym was very well equipped (not that I used it much!!!). Location is excellent – walking distance to everywhere we wanted to go – the best restaurants, Camana Bay and the supermarket literally right across the street. We stayed in a third-floor spacious beachfront villa and enjoyed the glorious sunsets on many evenings while enjoying our room service meal from LUCA and sipping prosecco – the dream! I would not hesitate in returning here again soon.see more
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
Caribbean Club - 4 Bedroom Villa at Seven Mile Beach - Book Now
Excellent Service and Location

The Caribbean Club is the best- so much more space than a hotel room yet all the same fantastic amenities you would get while staying at a hotel. We had dinner at LUCA on our first night- it was one of the best meals we had while on Grand Cayman. Me and my wife will be back again soon. Thanks for a great staysee 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

Also consider