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Vacation Rentals & Condos in Cayman Islands

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Vacation Rentals & Condos in Cayman Islands

About Cayman Islands

382 condos

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

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!

Responds fast! avg. 3 hours 8 minutes

Price per night from

$230

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3 Bed Condo with Huge Patio on Seven Mile Beach

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

“outstanding” The condo was very spacious, three large bedrooms & two full bathrooms! The kitchen was nicely stocked with assorted spices and coffee which we used every day. You can view the ocean from the kitchen, master bedroom and living room. The deck is huge which you can enter from either the master bedroom or living room. We sat at the patio table and watched several people parasail and at times a cruise ship would enter George Town harbor. We did soak up some sun on the patio and on the private beach, which also has a large swimming pool and pool bar with four TVs, food & drinks. We snorkeled every day right in front of the condo. We put our gear on at the private beach and swam to the coral reef which is loaded with ocean life to view. We saw lobsters, puffer fish, sting ray, barracudas just to name a few! The condo is located close to lots of fine restaurants within walking distance.

Responds fast! avg. 2 hours 17 minutes

Price per night from

$359

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2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 6

“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.

Price per night from

$190

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Designer Villa, in Tranquil and Beautiful East End

East End apartment

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 35 minutes

Price per night from

$375

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SMB-Grand 32, renovated 2Bd/2Bath,

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 24 minutes

Price per night from

$175

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Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt

North Side apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Home away from Home!” Loved location and the comfort of the house! Everything needed to enjoy the stay was provided and Rum Pointe is the best area on the island! Seidel Family

Price per night from

$275

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Three Little Birds -2BR+ Villa, Private Beach

Rum Point house

2 bedrooms / 2 bathrooms / sleeps 6

“Highly reccommended!” No matter if you are looking for some quiet time away...or a trip with your family...this is the perfect spot. My wife and I were looking for some quiet time and we got it as you have your own private beach. We also envisoned how much fun our kids would have here and look forward to bringing them with us next time. Fine dining and the local bar is across the street and we indulged both. All the fun activities you would ever want is only five minutes up the road (I highly reccommend the jet ski snorkling tour). The home is modern and very clean and whenever we had a question the local management team was extremely responsive. We will be back and couldn't be happier with our stay here and in the Cayman Islands.

Responds fast! avg. 3 hours 58 minutes

Price per night from

$310

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Coral Sands Resort: 2-BR, Sleeps 6, Full Kitchen

George Town condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 55 minutes

Price per night from

$199

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Luxurious beachfront, 2 bed, 2 bath, pool & tennis

Bodden Town house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 45 minutes

Price per night from

$180

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Sunset Cottage

West End house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$139

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2 BR condo on Seven Mile Beach with ocean views

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 51 minutes

Price per night from

$255

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Castaway by the Sea - Cottage

Bodden Town villa

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Price per night from

$199

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Spectacular Ground Floor Condo on Seven Mile Beach - Laguna del Mar

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 24 minutes

Price per night from

$650

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Beachfront Cayman Island Condo on 7 mile beach

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 7

“The ideal place to stay in Grand Cayman - highly recommended!” Fantastic location, just at the end of Seven Mile Beach where you'll want to spend a LOT of time, however it also has it's own private beach and snorkelling cove right in front (just below the apartment) which was virtually empty the entire two weeks we were there; it was almost like our family's own private beach! The snorkelling there was fantastic and my two young children loved to spend time there on the beach building sandcastles and also snorkelling, fascinated by the marine life. There is also a really lovely swimming pool for Sunset Cove with it's own swim-up bar. Again, not busy and a pleasure to spend time there. The apartment itself is on the second floor (the top floor) and on the end which means it has a very private feel especially as you relax on the balcony watching the sunset or indeed the sunrise! The neighbouring resort is set well back, so you do not feel overlooked in any way. The apartment is very spacious with 3 good sized bedrooms and two bathrooms. You can dine inside at the breakfast bar, the large dining room table or the large table out on the terrace and it's great to have that variety. The huge terrace makes the apartment feel even larger and the views from the terrace are second to none! Everything was in good working order, very comfortable and very clean. We used the dishwasher daily and also used the washing machine & tumble drier a few times. The owner was extremely helpful and responded so quickly to any queries I had. Her recommendations for where to go/what to do/where to eat on the island were invaluable and helped us enjoy the island to the max. We had a fantastic holiday and would definitely recommend this apartment and would happily stay there again.

Price per night from

$400

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Gorgeous Beachfront Villa, Azure Breeze #5

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!

Responds fast! avg. 2 hours 24 minutes

Price per night from

$274

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Cayman Brac Getaway--A Perfect Island Beach House!

Cayman Brac house

2 bedrooms / 1 bathroom / sleeps 4

“Perfect island getaway” Very clean house, nice construction with a sunroom with the nicest view on the ocean! Perfect for kids (includes Netflix) Very comfortable beds. 2 minutes away from the public sandy beach. Fully equipped kitchen with all the spices you need :)

Responds fast! avg. 1 hour 47 minutes

Price per night from

$149

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Ocean Retreat

West End cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 30 minutes

Price per night from

$115

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FALL SPECIAL - 6BR Modern Oceanfront Tranquility Cove by Luxury Cayman Villas

Grand Cayman villa

6 bedrooms / 6 bathrooms / sleeps 16

Price per night from

$2,300

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The Club at Little Cayman - Luxurious Living!

Little Cayman villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$500

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Morning Glory

Savannah villa

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$1,750

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Your Oceanside Retreat Awaits!

Old Man Bay apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect” I just spent a week with some friends at this Condo. It was even prettier in person then in the pictures. The location was perfect. Close enough to everything we wanted to do, but far enough away to get away from the crowds. There were 5 of us and the condo was plenty big enough to accomodate us. Since there are only 12 condo's in total, many times we had the private beach and pool all to ourselves. I would highly recommend this for anyone who is interested in visting Grand Caymans. I would love to go back there again!!

Price per night from

$225

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Cayman Conch Quest Beachfront Condo in Rum Point

Grand Cayman apartment

2 bedrooms / 2 bathrooms / sleeps 6

“A Grand Cayman Pearl for quiet enjoyment” We contacted the owner on line and received instant reponse to our inquiries and when we arrived at our designated time for a month we found everything that we had anticipated and more. The interior is bright and tropical and the kitchen was well equipment to accommodate whatever we decided to cook in house.The beds are comfortable and located so you can see, hear and smell the tropics.The snorkling off the beach is awesome when the water is calm and there are numerous sites within a short drive.Wifi TV and stereo were all there if you wished to use them. A vehicle is a must to get to enjoy the sites and venues of the island and to taste the Cayman cuisine. The management staff were at your instant call when needed. We would recommend this location and look forward to our return with family in the near future. Wayne & Mary Jane Dennis, Canada

Price per night from

$170

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Truly Oceanfront luxury in Grand Cayman

Old Man Bay apartment

3 bedrooms / 3 bathrooms / sleeps 6

“A Dream Getaway on Grand Cayman” What a great family getaway! We were looking for a warm place to bring our family before Christmas. We had never gone to Grand Cayman before. Our ideal trip is a sleepy place on the each that is very comfortable and well-appointed. We sure found that at this property. It was quiet (even close to the Christmas holidays). There is a beautiful pool right on the ocean and a protected cove full of multi-colored fish providing excellent snorkeling. The condo's balcony runs along the master bedroom and living room providing a wonderful spot to watch the sunset, read a book or enjoy a meal. Seven mile beach is the tourist area on Grand Cayman. It is mobbed with people, hotels and cruise ship vacationers. We found it far too chaotic for our liking. The North Side, where this property is located, is just the opposite and suited my family perfectly. The owner, Mark, was responsive and helpful as we planned our vacation. I could not recommend this place more highly.

Responds fast! avg. 1 hour 29 minutes

Price per night from

$225

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Private Villa on the Caribbean Sea - Stunning Views - Fall & Winter Specials

East End villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 24 minutes

Price per night from

$400

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# 115, Carib Sands Beach Resort - Cayman Brac

South Town apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$200

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Rest Azured

Little Cayman house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$700

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Laguna del Mar: Prime Seven Mile Beach location ground floor beachfront

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 24 minutes

Price per night from

$650

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Grand Cayman Islands Ocean front Villa with 2 bedrooms and 2 baths

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

Price per night from

$385

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Castaway by the Sea - Lodge

Bodden Town beach hut

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Price per night from

$159

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Beach or Pool

East End villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$290

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FALL SPECIAL - Luxury 3 bedroom mini-villa on private ocean-front cove

George Town villa

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$770

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Luxury Condo centrally located - Park Place (17)

Seven Mile Beach apartment

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$176

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29 Palms

Cayman Brac cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$135

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Crescent Beach (Sand) at Half Moon Bay

East End apartment

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 2 hours 41 minutes

Price per night from

$275

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New Listing - 3 Bedroom Ocean Front - Tranquil, Peaceful Location! Snorkeling!

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 42 minutes

Price per night from

$275

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FALL SPECIAL - 4BR on Seven Mile Beach - Serenity Now by Luxury Cayman Villas

West Bay villa

5 bedrooms / 3 bathrooms / sleeps 12

“Great property - highly recommend” Our party of six which included myself, my husband, three twenty-something adult children, and 85 year old mother were fortunate to spend Christmas week happily settled in at Serenity Now. The property and location were excellent. Sonya, the on island manager, was extremely hospitable, helpful, and accommodating. We loved the house layout, particularly the first floor bedroom and bath which were ideal for Grandma, and the four upper level bedrooms that each had wonderful ocean views. It was so relaxing to be able to return to the house after a day sight seeing, scuba diving, snorkeling, or visiting Stingray City and be able to relax by the pool and ocean, mix up some drinks, then either throw dinner on the grill or head out for a late dinner at one of the many excellent restaurants. Our stay couldn't have been better.

Price per night from

$1,275

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FALL SPECIAL - Chic 4BR Balinese - Stepping Stone by Luxury Cayman Villas

Grand Cayman villa

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,900

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Climbers dream island or relax and enjoy the view

Cayman Brac cottage

3 bedrooms / 1 bathroom / sleeps 6

“A Week in Paradise” This was our first trip to Cayman Brac, and we were shooting blind trying to find a place to stay. It was a somewhat last minute trip, and many places were already booked. Thank goodness we found Winta Cottage. It is as laid back and unspoiled as the rest of the island. We were met at the airport by the property manager, who was full of useful information about the island. The cottage has everything you need, without anything that will distract you from the natural beauty of the island. Amazing snorkeling right out in front of the house; wear water shoes! Beautiful sunsets from the deck, and hammocks for an afternoon snooze, not to mention an outdoor shower. I highly recommend staying here!

Price per night from

$150

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Viewing 38 of 382

About Cayman Islands

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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 among 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 vacation 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.

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