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Vacation Rentals & Condos in Cayman Islands

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288 condos

SMB-Grand 32. Beachside condo with pool. Remote work from Paradise.

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 15 minutes

Price per night from

$201

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

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$775

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

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Paradise” We stayed at MoodLight Kai condo the first week of april 2014. It was a magical experience being in Cayman Island for the first time. The condo is very modern and comfortable with a beautiful beach view right from the living room couch. There was no excessive noise or biting insects, the beach is very close and if you are feeling too lazy to go anywhere you can just lounge on the beach in front of the condo or soak in the jacuzzi. We had an excellent time and would definitely go back for another family vacation.

Price per night from

$258

Ocean Views Long Sunsets 25 steps to water Ground Floor, pool outside front door

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$343

Coconut Beach: Secret Garden Oasis with Palm-Shaded Beach and Spectacular

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 2 hours 58 minutes

Price per night from

$888

CAYMAN COTTAGE - on the "Golden Mile" fabulous, sandy beach with great swimming!

Cayman Brac cottage

1 bedroom / 1 bathroom / sleeps 3

“A private beach to watch sunrise and sunset.” We were at Cayman cottage this past February and our only mistake was staying such a short time (5 nights). It was so beautiful and restful. The property is very private and well stocked. It was clean and organized, with a large and airy living room, eating area, kitchen and very comfortable bed. Just outside there is a pleasant eating area and hammock. We loved sitting on the beach to watch sunrise or sunset. We also enjoyed snorkeling right in front of the property, which felt very safe and private. Sue was very pleasant and so helpful. We found that we could manage without having rented a car; we were able to walk to stores and restaurants and walk to rent bikes at the Scuba Shack. When we return we may rent a car for a few days to explore the Island more; some of the bike rides felt very long given the single speed bikes and the head winds. We are also tempted to return and learn to scuba dive. Sue's property is ideal for a couple, and also for two or three friends, or a family of three. Wherever we ventured each day, we were always so glad to come home to Cayman cottage and settle in for the evening. We did not grill but everything was there if we had wanted to do so. It felt like we had our own private place on Cayman Brac although we were visitors. We hope to return in the future.

Responds fast! avg. 2 hours 23 minutes

Price per night from

$170

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

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Loved it” We loved the Rum Point area. The condo was clean. Pool area was clean. We enjoyed the area enough for us to do. When we wanted to do more drove 45 minutes to Seven Mile Beach. Just a great location

Price per night from

$250

“Everything about this place is first class!” 3 King Bed Beachfront Villa

Cayman Brac villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 31 minutes

Price per night from

$400

Sea Beauty: ADA-Friendly Island Cottage w/ 300-feet of Private Beach, Hammocks

East End house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful, peaceful, relaxation!” My wife and I stayed at Sea Beauty last month with our son, his wife and our 14 year old grandson. Owners Cathy and Jerry Frazier met us at the door with the keys and gave us a complete walk-thru and instructions for the house. Nothing was left to be desired at Sea Beauty. It has been completely remodeled and appointed with only the best, leaving nothing to be needed. Sea Beauty is an ideal location, about 20 minutes to the shops and restaurants of George Town and 20 minutes to our favorite place on the island,Rum Point on the north side. The best part of Sea Beauty is its 300 feet of private beach with great snorkeling and swimming, and especially the hammocks under the sea grape trees,always in the shade overlooking the white sandy beach. This has to be one of the most relaxing, beautiful places anywhere! Also, it is only about 20 minutes to a full-service grocery store and five minutes to two nice restaurants, especially The Lighthouse, less than two miles away. We can't say enough about this beautiful home, renovated in the classic Cayman cottage style, and the helpfulness of Jerry and Cathy. They even supplied us with cell phones with pre-programmed phone numbers for certain services. We will certainly be returning to this beautiful paradise!

Responds fast! avg. 2 hours 58 minutes

Price per night from

$287

SUMMER/FALL RATES DISCOUNTED!/OCEANFRONT VILLA ON PRIVATE SANDY BEACH!!

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 52 minutes

Price per night from

$225

Ocean Wave: Indigo

Cayman Brac apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$147

2 BR condo on Seven Mile Beach with ocean views

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$315

Gorgeous Beachfront Villa, Azure Breeze #5

North Side villa

3 bedrooms / 2 bathrooms / sleeps 6

“What We Were Hoping It Would Be” No, really, we were hoping there would be oregano -- there was. We were hoping the knives would be sharp and that the dishwasher really washed dishes -- yup. We were hoping you really could snorkel out the back door and see fish you've only seen on TV and in aquariums -- absolutely. What we couldn't have hoped: that the cable would be wonky, I'd send an email, and ten minutes later the owner would call me personally to walk me through fixing it. That on a day too windy to go in the water, there would be so many things to do on the island (turtles, hikes, eating and eating and eating) that we wouldn't even care. Hopes exceeded. Such a great place to stay. Such a great owner. Clearly this is not a money-making investment. This is their second home that they let a few other lucky people use. I hope they rent this property as much as they can but always save some time for us.

Price per night from

$440

Rest Azured

Little Cayman house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$906

Suncoast # 4

Bodden Town apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$144

Two Rainbows: Beach Lovers Paradise in Cayman Kai w/ Pool & Beautiful Barefoot

Rum Point house

5 bedrooms / 4 bathrooms / sleeps 10

“Two Rainbows is a peaceful, secluded and affordable villa perfec” Our stay at Two Rainbows was our fourth visit to Grand Cayman. Check-in was absolutely painless. We had great instructions and were able to walk right in a get settled in a matter of a few minutes. Having previously stayed on Seven Mile beach and the North Side, we can say that it is our favorite location so far. If you want seclusion, peace and quiet, this is the place. If you want convenience to Georgetown and the action, this is not for you. We are used to driving a half an hour to get fuel or groceries, so it was no issue for us. If you visit in the winter, this villa is located out of the Christmas Wind that is prevalent on the North Side, which makes it much nicer to spend time on the beach. Speaking of which, the beach was clean and the water smooth. Snorkeling is limited and the swimming is less than ideal as there is a fair amount of grass in the shallows in front of the house, but if you feel like venturing out a bit farther there is some nice water to be had. The currents have washed quite a bit of sand around the point so the beach out front is quite wide and the water shallow. Kids will love it. We loved the screened in porch which allowed the breeze through, but not the bugs. The pool was small but adequate for a refreshing dip. The house was clean, roomy and well appointed with the exception of no stereo or outdoor speakers for music. We really missed that! There are several steps to get in or out of the house at every exit, so consider that for anyone in your group that has a problem with steps. Two hammocks are perfectly positioned and made for "naps with a view." A kayak or two would enhance the water experience since it is so calm in the bay. It is so convenient to Rum Point your will probably go there every day. The food there is exceptional. Overall, Two Rainbows is a really good value and a great place for a quiet beach get-away. We would recommend it to anyone who looking for laid back seclusion.

Responds fast! avg. 2 hours 58 minutes

Price per night from

$1,145

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

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 25 minutes

Price per night from

$773

Ocean Wave: Azure

Cayman Brac apartment

2 bedrooms / 2 bathrooms / sleeps 4

“The best vacation my spouse and I ever shared!!” Our first trip to the Brac was the best experience we have ever shared together. The warm hospitality of the Ryan family was boundless. Our anniversary gift from the Ryan family was spent purchasing snorkeling gear. I can't thank them enough for a vacation we will never forget.The villa was situated about 50 ft. from the ocean with spectacular snorkeling and sunsets. The villa was a beautiful 2 bedroom 2 bath and comfortable. The fishing was abundant with the native camaynians as a guide. We chose this island for the lack of tourists and the privacy for our 34th anniversary. We are hopefully returning to the Brac in February 2014.

Price per night from

$171

Ocean Retreat

West End cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 57 minutes

Price per night from

$144

Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 6

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect paradise” This was perfect for my family of 2 teenage girls, my wife and I. We wanted the hot Caribbean vacation without the resort. We dove and explored everyday. This condo had everything we needed, pool, right on the sea, internet, full kitchen, restaurants and great diving nearby, plenty to do. 80s during the day, 70s at night with that beautiful breeze, we hardly needed the aC at all. I would highly recommend this rental, we'll be back!

Price per night from

$334

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

Rum Point apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Tranquility” Traveled to Grand Cayman with a couple girlfriends and chose Kai Kotch based on reviews here and was not disappointed! We wanted a peaceful vacation and that's exactly what we got. Kai Kotch #17 was spacious and clean and we really enjoyed hanging out by the swimming pool and paddling in the bioluminescent pool. We were very close to many beaches (and much of the time they were private to us, as we traveled in the off-season). We couldn't have asked for more. When we had a question about something (like not being able to get the TV to work, or that the outdoor pool lights were off) someone was there to help us almost immediately. Tim adam was very pleasant to work with and also very courteous. We would gladly stay in Grand Cayman (and at Kai Kotch) in the future.

Price per night from

$378

Sea-Esta Beach Front Kaibo Condo

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$258

Cayman Beachfront at 22 Villas Pappagallo

West Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$259

Starboard Kai Beachfront Home with Great Beach Location at Rum Point, Cayman Kai

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

“Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the seven mile beach strip, since we heard that was very busy. We are so grateful that we found this wonderful townhome at Rum Point. Starboard Kai was very tastefully decorated, really clean and very well stocked. They even had a complimentary water cooler for us which were so helpful. They had three kayaks with life jackets, bikes (which we never got a chance to use), laundry in the unit (just make sure you bring your own HE laundry detergent), dvd player (I am not sure if we saw any dvds, but we hardly watched any TV since were had full days), coffee maker, spices, pool towels, beach toys. The only thing we needed was food, that’s how well stocked this place was. It was so nice to be right across from a Rum Point where our boys could play in the water, without worrying about waves. The location is superb, since you have the beach right in front of the condo and the beautiful bioluminescent bay in the back. It was so nice to lounge in the lanai and see the bay. From the living room and office you had nice views of the ocean of Rum Point. Many beautiful parrots, roosters and iguanas to see here, which was really neat! We did venture towards Seven mile beach and other areas of interest but wished we had just spent more time at our home base Starboard Kai. We checked out all the top beaches on the island and found our location to be #1. Janice the owner was a delight to work with; she really goes above and beyond to accommodate her guests. We also found Bob Wagner, the property manager very helpful as well. They truly excel in customer service and were very responsive to any issue we had. We loved going to the recommended restaurants. Loved our day at Sting Ray city, with Red Sail Sports which to sign up is right across the street and leaves from Rum Point’s pier. We really liked the blue iguana sanctuary nearby. We also have great memories of feeding the ‘Pirate’ Frigate birds at Tukka, a restaurant on the east end. Going to get sticky toffee pudding and seeing the Tarpons at Calypso Grill was fantastic as well. Would highly recommend this to others and have. When we got back we showed my friends and family and were amazed how beautiful everything was. Hoping to go back soon!

Price per night from

$458

KiToCay: Modern Beach House w/Over-the-Water Sun Deck & Private Beach Lot

North Side house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 58 minutes

Price per night from

$453

We'll Sea: Caribbean Cottage on Pristine Beach w/Seamless Indoor-Outdoor Living

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Price per night from

$458

3 Bedroom Plus Den Beach Front Home in West Bay - Sleeps 10!

West Bay villa

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,489

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

Old Man Bay house

4 bedrooms / 5 bathrooms / sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back yard made it great for relaxing. House has everything you need and some extras. We drove most days to Rum Point Beach( 10 minute drive) to relax, great beach. Spent a few days never leaving the property as we grilled fish we bought from local fisherman at the docks. With the big group we had, the villa suited us perfectly as there was plenty of room inside and out. I liked best the privacy and location of the house, we enjoy getting away from it all and this place gave us that. Worst part about the house is saying good bye.

Responds fast! avg. 2 hours 58 minutes

Price per night from

$630

Beautiful Sea Dreams Villa

Cayman Brac villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 8 minutes

Price per night from

$204

Lovely 'Sea Dreams Villa' w/ Private Beach & Deck!

West End villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$166

Palm Heights Residents #5

Camana Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$260

Kai Tana: Cozy Rum Point Cottage on Wide Sandy Beach w/ Awesome Snorkeling!

Rum Point house

2 bedrooms / 2 bathrooms / sleeps 4

“Tropical perfection!” Our group of three (two Biology Professors and a fiancee) stayed here for just four nights and we reveled in every minute of it. The directions to Cool Change were meticulous and we also asked for and were given directions to a grocery store. From the pictures on the website, we could not have imagined the sheer beauty of the villa and its setting right on the sea. The house was spotlessly clean and well furnished, nothing was lacking throughout our stay. The house sits on what seems to be a large plot of land, the neighboring houses are distant, and the beach (out the back door and down the stairs) is as close to private as you could desire. Large windows and sliding glass doors on the sea side opened out onto a lovely tiled terrace. A hammock hangs between two coconut palms and there is an outside shower to rinse off the sea water before entering the house. We had a wonderful time snorkeling and viewing the local fauna, including the small crabs and lizards that appeared on the terrace. We visited several nearby restaurants for dinner and enjoyed good meals at each one. I will look forward to returning to Grand Cayman and Cool Change again someday.

Responds fast! avg. 2 hours 58 minutes

Price per night from

$373

Morning Glory

Savannah villa

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$1,450

Just For Fun: Beach Bungalow on Glowing Bio-Luminescent Bay w/ Private Pool

Rum Point house

3 bedrooms / 2 bathrooms / sleeps 6

“Great Cayman Experience!!” We just finished our 1-week vacation at Just For Fun. The cute cottage certainly lived up to our expectations. Our family cooks three meals a day at home. The kitchen and new grilling area work perfectly. The kitchen has lots of extras that make cooking anything from a quick breakfast to a gourmet meal a breeze. Plus the wet bar with the wine fridge makes for a great flow of traffic. The outside area, with a pool, deck and a screened in porch is perfect. We ate every meal outside, either in the shade or by the pool. Plus there is a cute thatched hut with 4 showers in it for that quick rinse off after a swim in the ocean or a dive. This cottage would really be perfect for a locals getaway to the North Side. It has a great dock and it is very quiet. We will be back, Steve

Responds fast! avg. 2 hours 58 minutes

Price per night from

$567

Escape from Reality - Ocean Front!

West End house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 57 minutes

Price per night from

$177

Heritage House: Caribbean-Style Rum Point Villa with Large Pool & Sandy Shores

Rum Point house

4 bedrooms / 4 bathrooms / sleeps 10

“Wow! What a great time” We had the pleasure of staying at the Heritage House for a week at the end of april/beginning of May. The house is not centrally located to the the main part of the island, it is beautifully secluded on the North End of the island. We were within walking distance of Rum Point plus we could snorkel right off the beach at Heritage House. We traveled with our three adult children and their spouse or significant other. There were 8 adults in the house. Plenty of room for all of us. We would go back to Heritage House in a heartbeat. The pool out front was a plus. The weather was beautiful and the amenities were spectacular.

Responds fast! avg. 2 hours 58 minutes

Price per night from

$659

Kaibo Phase 2 - A4, Grand Cayman

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect vacation” My husband and I spent a week in this condo and found it to be perfect for us. It is very clean with nice linen and a well equipped kitchen. The location is great for walking around Kaibo. It is on a sandy beach with a restaurant right next door. We will definitely return to this spot. The beach is not good for swimming but there is a pool and hot tub. There is a beach within walking distance that is good for swimming.

Responds fast! avg. 1 hour 25 minutes

Price per night from

$201

Queen Room + Bath (Hibiscus Room)

George Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$155

Viewing 38 of 288
rentals in Cayman Islands

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About Cayman Islands

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.

Top Destination reviews

Cayman Reef Resort #33 - Personal Lanai Overlooking Beach & Ocean
Perfect location

We have stayed in a lot of rentals and this one was by far the best equipped, there wasn’t anything we could find that wasn’t there,it felt like they tried to think of everything you would need The location was perfect, right on the beach and close to all amenities , you could walk everywhere Totally enjoyed ourselvessee more
"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point
We love this place!

This is the second time that my wife & I have rented this condo. This time we brought 3 more friends. Plenty of room for everyone. This condo is so well kept & it has all your supplies in the kitchen, plenty of towels, even rafts & snorkel gear. The pool & ocean view are fabulous. We can't wait to go back again!see more
Gorgeous Beachfront Villa, Azure Breeze #5
Absolutely beautiful home and beach!

Beautiful beach home on the quieter end of the island. Snorkeling right outside your door. Close to Rum point , Starfish beach , and nice restaurants. Would HIGHLY recommend this place if you are looking for a great place to get some much needed rest and relaxation. Only thing I wish that was different, was that there wasn't enough dresser or closest space to fully unpack out of our suitcases in the two smaller bedroom.see more
SMB-Grand 32. Beachside condo with pool. Remote work from Paradise.
Recent Stay

We loved the location of this condo. It’s a quick walk to the beach and shopping and restaurants. It’s a quite complex, which we enjoyed. It was 4 adults for our stay, I would say this condo is better suited for a family. The 2nd bedroom upstairs is not really set up for a couple and the bathroom and shower are not ideal for anyone over 5’7. It could benefit from a full length mirror and TV in the bedroom upstairs. It could use some attention, the walls needed painted or scrubbed, the master bathroom was missing a towel rack, the closet doors where the washer and dryer are located are very hard to open. With all that said, I would recommend this unit to anyone visiting Grand Cayman. It’s a great value and location.see more
Cayman Reef Resort #50 - Best Value on the Beach
Beautiful condo

We love the Cayman Islands and have stayed many times at the Cayman Reef Resort. Marc’s unit #50 is a one bedroom beautifully updated, decorated, and furnished with everything you will need for an awesome Seven Mike Beach vacation. Highly recommend # 50!!! … see more
Just Chillin
Just Chillin

Very close to the airport, bars, restaurants, grocery store, etc. Must love friendly dogs, who bark every time you depart or arrive on the property. Property owner Dianne is a great host! Very helpful and giving. She even had fresh organic eggs and homemade pepper jelly for us. … see more

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