Grand Cayman Rentals with Pools

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128 condos in Grand Cayman with pools

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

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$384

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.

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$287

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

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Winter Getaway” This was not our first trip to Grand Cayman and we are very familiar with the island and what is available by way of accommodation. We have always been partial to the North Side. It offers the peace and tranquillity that you cannot find on 7 Mile Beach and “A Mid-Winter Night’s Dream” has definitely offered us the best experience so far. The condo was as described, very clean and so well equipped, we wanted for nothing. Definitely the best unit in the complex. We had a direct unobstructed view of the ocean and although we had planned to eat dinner at nearby restaurants, we spent most evenings dining on the lanai listing to the sounds of the ocean. Great snorkeling, very private beach and surrounding area. My husband and I highly recommend this property. Many thanks to the Lang family for sharing and a special thanks to Dan, it was a pleasure dealing with you.

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Price per night from

$281

Coconut Beach: Rum Point Beach House w/Pool, Beach Cabana, & Spectacular

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$946

2 BR condo on Seven Mile Beach with ocean views

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$573

“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!

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Price per night from

$373

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.

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Price per night from

$630

“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!

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Price per night from

$459

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

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Price per night from

$567

Great Location & Value! 7mile Beach Condo next to a Resort Hotel!

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$687

Boggy Sands Club - Parrot Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 23 minutes

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Price per night from

$2,291

Boggy Sands Club - Seven Mile Beach - Starfish

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Phenomenal experience!!” We stayed at this property in February 2012 and from the warm greeting at the airport to the beautifully decorated and well equipped condo, we had an extremely comfortable and relaxing holiday! We can't thank the owner, Morne, enough for the exceptional service, accommodations and overall experience at his property in the Cayman Islands! We travelled to the Island with our toddler and Morne made our packing and travel very light and easy by providing all things baby related - we didn't need to bring a stroller or even any toys. Our son was absolutely spoiled with a full sized crib, adorable bedding, a huge selection of toys and even a highchair. Having everything at the condo waiting for us was an absolute treat! Morne was always available to us by phone and email - he was very quick to respond to any questions or requests. The grounds and pool were expertly maintained and always clean. The condo is located just a short walk from the beach - which we usually had all to ourselves. This property truly made our vacation feel like a peaceful getaway with a private beach. We felt extremely spoiled and well cared for during our time at this property and truly thank Morne for his exceptional hospitality (and apologize for how incredibly over-due this review is)! Almost a year later and we still think back on our amazing time there and can't wait to go back some day!

Responds fast! avg. 15 minutes

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Price per night from

$2,290

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$458

Great Escape: Serene Cove Villa in the Quiet Neighborhood of Cayman Kai with

Rum Point house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Best. Vacation. Ever. Amazing. Beautiful. Relaxing.” Great Escape is a beautiful home in the perfect location. A truly luxurious property with an amazing pool and a short walk to Rum Point Beach, which is fantastic. I can't say enough about the house, the pool, the beach, the island. It truly was a perfect vacation. Although it is a drive to the other side of the island, we preferred the relaxing, quiet and island feel of Cayman Kai. The photos of Great Escape are very accurate except honestly I think the pool is bigger than it looks in the photos. Grand Cayman Villas handled our reservation in a professional, timely and courteous manner. They answered all of my questions promptly. They provided lots of information about the island, the property, restaurants, car rentals, etc. Upon arrival there were a couple minor issues (not worth mentioning) but the Villa Manager answered my call immediately and things were taken care of within 20 minutes. The owners of the property were a pleasure to deal with as well. We received an email from them before our stay with helpful information about the property and the island. We spoke by phone and met in person briefly on arrival. They were nothing but helpful and friendly. Highly recommend Great Escape and Grand Cayman Villas. It might be a few years but we will definitely be back.

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Price per night from

$911

Cayman Conch Quest Beachfront Condo in Rum Point

North Side 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

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$258

Cayman - SAND at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$396

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$602

Ocean front Villa Grand Cayman

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$487

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

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$568

Hidden Cove: Family Hideaway w/Free Kayaks & Bikes, Private Pool and Dock

Rum Point house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Beautiful house/location...but erroneous charges from owner not” This is a truly wonderful vacation rental...beautifully decorated and well situated in the cove allowing both privacy and easy access to the ocean. We had a large group and I can easily say we all agreed it was a magical spot worth returning to...especially given the bioluminescene right in our cove which we enjoyed every night! Our other concern was access to the grocery store which turned out to be a shorter drive than expected (maybe 20 mins). All was well until we checked out and the owners slammed us with erroneous charges for missing items! We were never given an innitial inventory, yet we received a massive bill and automatic charge from the owner. They even charged us for items they admitted were missing before we arrived. It was a ridiculous ending to a wonderful trip and it left us all with a bitter taste in our mouths. If you're a strong negotiator, perhaps this rental is worth your trouble.I would certainly recommend getting an inventory pre-visit and writing into the contract that you would only be held accountable for those items listed.

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Price per night from

$911

Cayman - SKY at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$396

First Floor Oceanfront Condo in Top Location!

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Conched Out: Beach House w/ Backyard Snorkeling + Private Pool

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$453

Fischer's Reef: Spacious, Luxury Beach Villa w/ Heated Infinity Pool & Amazing

Rum Point house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 20

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Price per night from

$6,704

Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Cayman Dream” We rented Cayman Dream in early June of 2013. We were very happy with the house. It's exactly as the pictures show. The kitchen is very well appointed and the grounds are kept very nicely. It's located in a nice quiet area with very little traffic. Our only complaint with the house was the phone/wifi. It was out for three of the six days that we were there and even after it had been fixed we had to constantly reset while we used it. With our children back in the states, we felt really out of touch. We truly enjoyed our stay and would recommend staying there.

Match: Swimming pool

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Price per night from

$487

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Price per night from

$1,313

Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront.

East End house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$682

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Price per night from

$1,598

Boggy Sands Club- Stingray Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Heaven on Earth in Grand Cayman” The reviews and pictures don't begin to do this Boggy Sand Road property justice! We rented the ground floor unit,which was absolutely spotless, elegant, roomy, well-equipped and only a few steps to the most beautiful beach. The area is residential, private and quiet - like we had somehow privately rented Seven Mile Beach! The grounds of the property were garden-like and the pool was lovely and clean. Our rental car was nice to have but not necessary - there is a Foster's Market within a short walk of the condo, as well as a few great little restaurants (Alfresco's, Timbuctuu and Heritage Kitchen). The bus service is great - more like hailing a cab with pick-up right at the foot of the driveway. But back to the beach...the unit is equipped with 2 kayaks and a paddle board, which we enjoyed tremendously on the calm, crystal-clear waters. Cemetery Beach is right next door for some of the best snorkeling we had ever experienced. The Kittiwake Shipwreck is directly off shore for another fantastic snorkeling experience. We even enjoyed swimming with our own resident sea turtle every day! The condo unit itself was spacious and fully equipped with everything you need - beach towels, chairs, umbrella, rafts and cooler;fully-equipped, gorgeous kitchen with granite counter tops, beautiful and spacious bathrooms, and super-comfortable beds. Although our "kids" were 15, the unit would be wonderful for families with smaller children as well. I must say, the absolute best part, however, was our gracious host Morne, who made us feel like pampered family members visiting from out of town. He picked us up from the airport, made sure we had everything we needed, made great recommendations for activities and restaurants, was never intrusive but always available for anything we needed. I would (and will) vacation here again in a heartbeat, and make the highest recommendation to anyone to enjoy the vacation of a lifetime at this property! Just please don't take the week I want! ;)

Responds fast! avg. 15 minutes

Match: Swimming pool

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Price per night from

$2,290

Cayman Reef Resort #50 - Best Value on the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great location, Great value, Great accommodations” The best way to express my wife’s and my satisfaction with this condo is, this was our third consecutive stay here. My wife and I have been coming to the Caymans off and on since 1985 and have stayed in several other accommodations over the years, but this is by far our favorite. We have had the pleasure of meeting Marc (the owner), and I am impressed with his attention to detail, helpfulness, prompt response to any questions, and his overall commitment to making his guests visits trouble free and enjoyable. The location is excellent and the beach area is as good, or better, than any other spot you will find along Seven Mile Beach. There are fine restaurants and shopping within easy walking distance of the condo, making the need for a rental car only an option not a necessity. I feel strongly that this is the best overall vacation value on the island. My wife and I see no reason to look elsewhere for our future trips to Grand Cayman.

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Price per night from

$516

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$682

Cayman Reef Resort #1 - Renovated Seven Mile Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Immaculate, Convenient, Detailed - Awesome Location!” We've been to Cayman many times and this location was super for a party of two. The walking convenience to the beach and Camana Bay areas made it super. The details of manuals provided, communication with the owner, and cleanliness were all much appreciated!

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Price per night from

$567

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Price per night from

$1,146

Northern Lights #5: 2-Story Townhome w/Backyard Snorkeling, Shared Pool + Dock

Old Man Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$338

CaymanOnTheBeach

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 8 minutes

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Price per night from

$373

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Price per night from

$401

Modern condo steps from the beach

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$630

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Price per night from

$468

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