North Side Rentals

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189 Houses

"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.

Price per night from

$280

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. 3 hours 59 minutes

Price per night from

$451

Gorgeous Beachfront Villa, Azure Breeze #5

North Side villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“perfect getaway for island living” My husband & I had decided to take our 3 teenagers for their first trip abroad and their first beach/ocean vacation, and a number of factors led us to choose Grand Cayman. We absolutely did not want the "resort" experience, which tends to be largely the same no matter where the resort is located. After extensive research my husband found Frank's villa and this place is what made our vacation unforgettable. The north side of the island is much quieter than the Georgetown/Seven Mile Beach area where all the cruise ships land, and it has a more unspoiled beauty. Although there were residents in the other villas, we almost always had the beach to ourselves and some of the best snorkeling on the island was right out back. Every evening the kids researched new snorkel sites to try out, and with every new site they made the same comment: "Our" backyard has better snorkeling. The fact that they considered it "our" backyard speaks to the homeyness of this villa--Frank & Del have truly thought of everything and our stay was very comfortable. I want to also point out that our family always tries to rent a house when we travel--with 2 teen boys and a teen girl, having a house is so much more enjoyable than staying at a hotel--and this is the best experience we've ever had. Frank & Del have gone out of their way to set up the villa so that any guest can enjoy it to its fullest, and Frank was a wealth of information prior to our trip. I really kept thinking he would tire of my husband's seemingly endless questions, but Frank provided so much information about the island that we were able to plan an absolutely amazing adventure!

Price per night from

$451

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$455

Castaway Cove: Tropical Beachfront Villa with Superb Snorkeling and Coastal

North Side house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great Villa” We loved Castaway Cove. It is very clean. The kitchen is totally equipped with everything you need. Other renters left things so we did as well. The beach towels and cooler was great. We used them every day. The grill wasn't the best but served our purpose for the one time we grilled. It is very quiet so sleeping was no problem. One morning there was a bulldozer clearing the lot next door. So there was that noise. Not a good swimming beach. Lots of sea grass. We saw some wierd things in the shallow water so my daughter and I wouldn't swim in it. The bedroom were very comfortable. The showers were great. A problem we did have was at night when we wanted to go out on the dock in the cabana to have a drink there was a couple fishing. The first night they scared us. The woman came running up saying they lived across the road and had permission to use it. We thought okay but didn't think they would return since it was clear we were renting it. Well, sure enough they were there again the next night. My husband called the next day and mentioned this and they didn't come after that. But, there were two nights we couldn't use it. You would think they would have stayed away when the villa was rented out. The other thing we didn't like was the sea grass. It was so high you couldn't swim over it. We didn't feel comfortable walking through it because we saw stingrays and some sea creatures we have never seen before and didn't know if they stung.

Responds fast! avg. 3 hours 59 minutes

Price per night from

$485

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

Price per night from

$200

Responds fast! avg. 3 hours 59 minutes

Price per night from

$599

Beautiful White Sandy Beach. Specials: Stay 7 nights pay only for 6 nights

North Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$451

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

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$451

Luxury 3bd Beach View, # 2 Peach, Stunning Views

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$326

Luxury 3bd Beach View, # 3 Blue, Stunning Views

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$375

Luxury 3bd Beach Front, # 4 Green, Stunning Views

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$395

Luxury 3bd Ocean View, # 1 Cream, Stunning Views

North Side house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$305

Luxury 3bd Beach Front, # 5 Yellow, Stunning Views

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$395

Best vacation in Grand cayman, the North Side Rum Point area

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$308

Spacious 2-Bedroom 2-Bathroom Beachfront Condo with Heated Pool

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$219

Great rentals within 20 miles that match your search

Castaway by the Sea - Cottage

Bodden Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$239

Castaway by the Sea - Lodge

Bodden Town beach hut

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$204

Coconut Cottage

Bodden Town cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$570

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 59 minutes

Price per night from

$565

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.

Responds fast! avg. 3 hours 59 minutes

Price per night from

$485

Sea Cove: Cayman Kai Villa w/ Private Dock & Waterfront Sun Deck for

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great vacation!” There were 4 of us - 2 couples - and the house was great! There were many activities near the house and the 7 mile area is only a drive away. The beach was great, very secluded!

Responds fast! avg. 3 hours 59 minutes

Price per night from

$394

“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. 3 hours 59 minutes

Price per night from

$371

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 59 minutes

Price per night from

$906

Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage

Old Man Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

“A wonderful, relaxing paradise” I recently stayed at Cayman Sands with my husband, my in-laws, and our 2 young girls, ages 4 and 6. This home is everything we could have asked for - as gorgeous as the pictures, but even fresher (the larger bedrooms have been painted since the online photos). It was very spacious and clean, and the location was great for us - quite private (even with folks staying in the neighbouring home) but a quick drive to Rum Point, which is a great beach for families with young kids with its calm water, extended shallows and sandy bottom. We had the pool heated - well worth it - as our daughters spent long hours in the pool. The beach area is nice - although it is true the water in this area is more suited to snorkelling than swimming or wading, it was fine for us with the pool right there for the girls, and snorkelling convenient for us. There is washed up plastic garbage if you walk off the property down the beach - which is not the fault of the property managers or the island, but an unfortunate consequence of garbage mismanagement elsewhere and tides/storms washing debris onto the shore. The villa is well stocked with kitchen items, pool toys, beach towels, etc... We took a great glass-bottom boat tour from Rum Point with Red Sail Sports - to Stingray City and for a bit of snorkeling. This was a nice way to go as the boat is smaller, so fewer people and plenty of time for everyone to handle the stingrays and get photos and video without feeling rushed at all. Did some nice diving off Macabuca near the Turtle Farm - can rent gear right there. I would recommend this villa without hesitation, and hope to stay here again in the future. Cayman is a beautiful, safe island, and easy to explore since it's not too big. Jim Leavitt and his staff were wonderful to deal with throughout our searching for and booking of this villa, and provided great information to us before we arrived. The cleaning lady who came mid-week (Sharon) was friendly and efficient.

Responds fast! avg. 3 hours 59 minutes

Price per night from

$906

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 59 minutes

Price per night from

$627

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$679

Cayman Reef Resort 56 - Luxury on Seven Mile Beach

Seven Mile Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“We all loved it!” We had a group of 6 women that stayed for a week in February. This was everything and more! It had everything that we needed. We were on the beach most of the time and it was awesome. The pool was nice, too, but we are beach girls and love to people watch! I would definitely recommend this to friends and families. We used the washer and dryer daily. Didn't do a lot of cooking, but there was every appliance we would need. Loved sitting on the screened in deck in the morning with coffee and just relaxing before we went out for supper. Sandy at the front desk was a great help. too.

Price per night from

$1,134

Ocean front Villa Grand Cayman

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 44 minutes

Price per night from

$456

SMB Area Private Villa From $2100/wk

West Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Really nice place” Quiet and comfy. This is the Cayman I remember from trips in the past. Lots of things within walking distance, like a grocery store, public beach and several good restaurants. Its away from the tourist area of George Town. You will need a car to get around.

Price per night from

$399

Island Gem

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Perfect Island Getaway!” My husband and I spent a week here for our honeymoon in April. We could not have asked for a more perfect getaway. Lee was responsive and resourceful right from the start. She answered all of our questions and made sure we had a thorough list of what to expect upon arrival and throughout our stay. We arrived on a Sunday afternoon and were welcomed at the Villa. We were given a tour of the Villa and had an opportunity to ask questions and get settled. The condo was better than we had expected - the photos of this property do not do it justice. The kitchen is fully equipped, living room is comfortable, bedrooms are large and the bathrooms both include a shower with great water pressure. There is a dishwasher and washer/dryer right in the unit. The entire condo is very tastefully decorated. Everything you could possibly need for a comfortable stay is here, it's just like being in your own home. The beds were comfortable with soft, clean sheets and plush pillows. There were more than enough beach and shower towels. There is a TV with cable and plenty of board games. Each room also has a large closet and has an outside balcony with seating. The balcony off the living room overlooks the pool and beach area, providing an excellent view of the property. Villas Pappagallo is secluded from the rest of the island, providing a relaxing, secluded area to refresh and rewind. There is a national park directly beside the Villas with a beautiful, natural landscape and a perfectly quiet place to walk along the beach. Seven Mile Beach is a short car ride away and Georgetown just a bit further. The entire island is accessible from Villas Pappagallo. We were so pleased to be staying in West Bay. Our two favourite restaurants were Ristorante Pappagallo and Cracked Conch, right in West Bay. Ristorante Pappagallo is just steps away from the Villa. The snorkelling and sunsets on West Bay were also highlights. We took a trip to rum point for an afternoon for snorkelling and lunch. This is an easy day trip in the car. There are so many things to see and do on the island, but we spent most of our days on the beach right out front Starfish Villa. The property was quiet and all neighbours were friendly and respectful. We cannot wait to come back to Grand Cayman. We will absolutely stay at Lee's condo at Villas Pappagallo again. I cannot think of one single disappointment or criticism. Great Vacation!!

Price per night from

$656

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

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$565

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

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$451

Boggy Sands Club on Seven Mile Beach - CORAL 1

West Bay condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 16 minutes

Price per night from

$2,279

Ocean Paradise # 5 Yellow - Affordable Luxury Home w/ pool

Rum Point villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$683

Cayman - SAND at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$394

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

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$382

Luxury Condo #2 on Boggy Sand Road-Garden Level

Seven Mile Beach apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$512

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Top Destination reviews

Cayman Conch Quest Beachfront Condo in Rum Point
Great Condo to Rent

We would agree with all of the positive reviews for this condo. We stayed a week in early January. The condo is very comfortable; it is actually even nicer than the pictures. This condo is extremely clean and well maintained. The beds are very comfortable; there are plenty of beach towels, bath towels and linens. There is a TV ( gets all kinds of channels) stereo, Ipod docking; DVD player- more than you need. The artwork in the condo is very nice. The screened in lanai is great for meals and to just watch the ocean. The pool is clean. The complex is small and is kept immaculate by the management company. It was windy the week we were there so we were not able to swim/snorkel out front. Loved having the beach chairs,mats,bags and cooler to use. Bob replyed to all of my emails thoroughly and quickly. There is detailed information Bob emails to you and there are 2 notebooks of information at the condo. It is very quiet and peaceful. The drive is approx 40 minutes from the airport. Bob recommended Marshall's car rental and we found them to be great. This was our first trip to Grand Cayman. We would without a doubt recommend this condo.see more
"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point
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 … see more
Castaway Cove: Tropical Beachfront Villa with Superb Snorkeling and Coastal
A Family Vacation to Remember forever

We had an amazing stay at Castaway Cove. It is the location to be when visiting Grand Cayman if you don't want to be by the tourists and busy 7 mile beach. The weather was amazing and the beach was great. My kids loved snorkeling off the pier. The house was completely stocked and the serenity and peace of the totally private beach house was amazing.see more
Gorgeous Beachfront Villa, Azure Breeze #5
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.see more

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