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Cayman Islands Rentals with Pools

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198 condos in Cayman Islands with pools

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 1 minutes

Match: Swimming pool

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Price per night from

$202

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

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Price per night from

$659

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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Price per night from

$259

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

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$344

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

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$892

"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

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$253

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

Cayman Brac villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 30 minutes

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Price per night from

$401

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

$317

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. 3 hours 5 minutes

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Price per night from

$1,150

Sea-Esta Beach Front Kaibo Condo

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$259

Cayman Beachfront at 22 Villas Pappagallo

West Bay apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$258

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!

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Price per night from

$460

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. 3 hours 5 minutes

Match: Swimming pool

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Price per night from

$633

Palm Heights Residents #5

Camana Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$262

Morning Glory

Savannah villa

7 bedrooms / 6 bathrooms / sleeps 14

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Price per night from

$1,457

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. 3 hours 5 minutes

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Price per night from

$570

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. 3 hours 5 minutes

Match: Swimming pool

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Price per night from

$662

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 35 minutes

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Price per night from

$203

Contemporary open house, spectacular ocean views, butterflies, sweet sunsets

West End house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$225

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

$459

Kai Vista: Sandy Oceanfront Villa with Infinity Pool, Jacuzzi, and Beachfront

Rum Point house

4 bedrooms / 4 bathrooms / sleeps 9

“The best vacation I have ever had!” We had the most fantastic vacation ever. Kai Vista has it all - a beautiful and very spacious villa that accomodates your every need and is so family friendly. It is perfectly designed for comfort, relaxation and enjoyment. The kitchen is well equipped with modern appliances and plenty of counter space for preparing your meals. It was nice having a washer and dryer so we didn't have to lug home dirty laundry. Our family comprised of six adults and four girls ages 8 - 10 and we were never bored nor did we feel crowded - we had plenty of room inside and out. There is a wonderful sea breeze that is almost constant so even though the weather was 85-90 every day you don't really feel it. I think Kai Vista has the best beach and location on Rum Point. The infinity pool is gorgeous as is the entire outside patio and beach area. We all enjoyed it so much we hardly strayed far to explore the island since everything is right there. Snorkeling was the best experience for all of us - we snorkeled every day with the girls. We saw all kinds of tropical fish and sea turtles too. We also kayaked and biked around Rum Point which is so pretty. There is a very nice gourmet restaurant on Rum Point within walking distance and also an outdoor grill right on the beach. We can't wait to come back to Kai Vista. The girls cried when our week was over because they had so much fun.

Responds fast! avg. 3 hours 5 minutes

Match: Swimming pool

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Price per night from

$857

4BR Seven Mile Beach - Boggy Sands - Parrot Penthouse (P3)

Seven Mile Beach condo

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$1,160

Sea Breeze, a luxury SMB beachfront condo

Seven Mile Beach apartment

4 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$3,438

4BR Penthouse Boggy Sands Club - Seven Mile Beach

Seven Mile Beach condo

4 bedrooms / 4 bathrooms / sleeps 10

“Best Family Vacation Ever!” We came to Grand Cayman to scuba dive as a family. Our condo was a wonderful place to relax after our dive trips because of its proximity to the beach and the pool. Boggy Sands Beach Club is within walking distance of some great local food. Heritage Kitchen, ALFresco, and Calico Bar. The owner Morne Botes was attentive to all of our needs and great to work with. We highly recommend this place and hope to return very soon.

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Price per night from

$1,149

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.

Responds fast! avg. 3 hours 5 minutes

Match: Swimming pool

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Price per night from

$800

Condo on 7 Mile Beach - Great Location - Ground Fl

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$202

Reef Romance: Ultimate Friendcation Getaway w/ Outdoor Bar, Private Pool

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 10

“Fantastic relaxing villa!!” The house was perfect for our group of 10 - our three adult children, their friends and our relatives! Five bedrooms with each room having their own connected bathroom. Everything we needed was provided - the kids loved the hammocks, beach and sun! We loved the family meals and playing board games at night - something we had never done before! We would highly recommend the house and rental company. Any problem that popped up was handled immediately - one time within 10 minutes! My wife found the kitchen fully equipped and the outdoor BBQ was great. The house is on the north side of the island - far away from the tourist spots in the city, but only 15 minutes away from stores and shopping, and 30 minutes from the airport. You will need a car - we had 2 which made getting around a lot easier for a big group. The weather was fantastic - only rained one day early in the morning. Rum Point beach and outdoor restaurant is 4 minutes down the road. Several family members visited the Botanical Garden at Frank Sound and really enjoyed it. You will need beach shoes as the shore behind the house is a bit rocky. We had a great 9 days and have memories we will cherish for life!

Responds fast! avg. 3 hours 5 minutes

Match: Swimming pool

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Price per night from

$1,265

Crescent Beach (Sand) at Half Moon Bay

East End apartment

3 bedrooms / 3 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$319

Lime Tree Villa

Camana Bay villa

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$598

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

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$442

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

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Wonderful Stay, Beautiful Condo and Grounds, Easy to Work With” Condo is beautiful and exactly as described in the listing and in all communications with Marc. Very close to beach and water. Even closer than looks in pictures. Literally few steps out the door. Also close walk to great restaurants, stores and Camana Bay. Unit well equipped with towels, umbrella. Beach is gorgeous with beautiful turquoise warm water. Pool and grounds immaculate. Well maintained. Pretty landscaping. Enjoyed the screened porch with ceiling fan for morning coffee. Most gorgeous sunsets on the island right outside of the door. Marc was easy to work with ..... from the time of booking and throughout our stay. He touched base by email and phone upon our arrival to ensure we were doing ok. We would not hesitate to book again .... amazing experience.

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Price per night from

$568

YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$328

Babylon Reef: Recently Renovated Villa with Backyard Snorkeling and a Crystal

North Side house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$604

First Floor Oceanfront Condo in Top Location!

West Bay apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$231

Crescent Beach (Sky) at Half Moon Bay

East End apartment

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$344

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.

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$805

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