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North Side Rentals

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262 Houses

"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

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

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

$439

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

Rum Haven

North Side apartment

1 bedroom / 1 bathroom / sleeps 4

“Rum haven.” Super place. We loved it. Everything we needed. Clean and tidy. Great location. Nice owners. Fantastic staycation destination.

Price per night from

$145

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$417

Castaway Cove: Tropical Beachfront Villa with Superb Snorkeling and Coastal

North Side house

4 bedrooms / 3 bathrooms / sleeps 10

“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.

Responds fast! avg. 2 hours 58 minutes

Price per night from

$476

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

North Side house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Price per night from

$602

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

$456

Rum Sands

North Side apartment

1 bedroom / 1 bathroom / sleeps 4

“Sweet Paradise” A great place to enjoy the sea, sun and sand in Rum Point. The cottage had all the necessities of home and a perfect match for our family of four with two small children. The updated kitchen was great and one of the draws to the cottage with a family who enjoys cooking and well kept. The views out the front (Rum Point) and back(Cove) were amazing and we just couldn't get enough of the sunrises and sunsets.

Price per night from

$145

Conched Out: Island Chic Bungalow w/ Lush Tropical Landscaping,Pool & Backyard

North Side house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Price per night from

$315

Sea Magic

North Side villa

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$335

Goat Kai - Sealodge # 17

North Side apartment

1 bedroom / 1 bathroom / sleeps 2

“Kozy Kai Sea Lodges” We stayed 9 days in August. Noelle for booking and Sislyn as property manager took great care of us getting settled in. The unit was clean and everything was operational. The location was what sold us...just swim out to the reef for some amazing snorkeling. Seas Lodges was quiet even though others were staying there. Very relaxing sitting out on the covered patio. Cannot wait to get back...

Price per night from

$170

Villa Bellagio

North Side villa

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$675

Kaibo Yacht Club #9C

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$225

The Pools #10

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Celebrating 40th Birthday and 1st Anniverssary” Everything was very relaxing. We enjoyed ourselves. The pool was clean and so were the rooms. Would suggest a bit of an update on the furniture and window shading in the room on the bottom floor. But besides that everything was very nice.

Price per night from

$195

Henry's Hideout

North Side villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$425

Kirk Kove

North Side villa

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay on the cove” My wife and I and two children (ages 20 and 15) enjoyed a stay-cation at Kirk Kove. The villa was clean and well appointed with a large sandy beach with volleyball net, an enormous cabana with BBQ, and a boat dock. Despite initial problem with the WiFi not working (resolved after the technician finally turned up), and a few rusty door hinges, we had a glorious time enjoying early morning beach strolls, swims, (rented) paddle boarding and kayaking. We used our car to drive to restaurants at North Side and East End and our boat for trips to Hurley's for shopping and the sandbar for swims with the stingrays and the reef for snorkeling. All in all a wonderful relaxing get-away.

Price per night from

$225

Mahogany Point 2

North Side townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$300

Villa Emmanuel

North Side villa

5 bedrooms / 4 bathrooms / sleeps 10

“A fabulous week at Villa Emmanuel” Two families (4 adults 4 children ages 2-8) just returned from a wonderful week at Villa Emmanuel. The house was spacious with a nice pool and sandy beach area. There were some jelly fish and/or sea anemones that were stinging so beware. We tried to stay only on the sandy patch except when snorkeling. Snorkeling from the house we saw lobsters and a lion fish. The majority of homes on the inlet had their hurricane shutters up so we enjoyed privacy & tranquility. The kitchen has everything you need to prepare meals and the pool had rafts and toys. Additionally, there were some beach toys at the beach area. The views from the home are spectacular and the sunsets beautiful. Since it's a rental some of the furnishings are a bit worn, as are the pool and beach chairs but this didn't prevent us from having a wonderful time. The huge screened in porch is terrific and the upstairs master suite is amazing. Highly recommend this home and hope to get back soon!

Price per night from

$750

Villa La Playa

North Side villa

4 bedrooms / 4 bathrooms / sleeps 9

“Perfect Paradise= La Playa” The perfect place for a family. An open floor plan made life easy to multitask and relax. Management was very responsive. We needed a coffee pot and before we could blink- we had a new machine. We wish we could have remained forever.

Price per night from

$525

Beach Plum Villa

North Side villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$475

Kaibo Yacht Club # 29C

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great quiet location and beautiful sunsets.” Great quiet location. Very well maintained buildings and grounds. Wonderful pool and beach area, perfect for young children or adults that want a nice quiet getaway... Would go and rent again !!

Price per night from

$210

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 2 Peach

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$512

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 3 Blue

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$512

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 4 Green

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$669

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 1 Cream

North Side house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$512

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 5 Yellow

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$669

Great rentals within 20 miles that match your search

OCEANFRONT LUXURY RENTAL REGAL BEACH CLUB UNIT 121 CAYMAN ISLANDS

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$644

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.

Price per night from

$638

4BR Seven Mile Beach - Boggy Sands Club - Parrot 1

West Bay apartment

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,291

Sea Jewel, 2BR, 2BA, oceanview villa

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$511

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

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$499

Majestic Luxury Private Home On Seven Mile Beach

George Town villa

6 bedrooms / 5 bathrooms / sleeps 17

Price per night from

$3,494

4BR on the Pool at Boggy Sands Club, Seven Mile Beach.

West Bay condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,293

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

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$369

Sandbar Beach Island House 11, steps from Rum Point, FREE kayaks, bicycles, WIFI

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$486

⭐Plantation Club Vacations - Elegant Ocean View Condo⭐

Seven Mile Beach condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$620

Viewing 38 of 262
rentals in North Side

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Top Destination reviews

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point
What a wonderful place!

If I could give this 6 stars I would. The condo was absolutely perfect. Beautiful & clean. Everything you need. Dan was so helpful. Before we arrived, he sent us a package telling us of all the best places to go & where to shop and some hand detailed maps. Such a beautiful ocean view from the condo. If you go, be sure to go tyo Sting Ray City & the sea turtle park.We have vacationed many time & I will say that this is right up there at the top of the list of our most favorite vacations. We will be back! Thanks so much for your hospitality Dan.see more
Gorgeous Beachfront Villa, Azure Breeze #5
Thumbs up for Azure Breeze #5

We had a terrific stay at Azure Breeze #5. The home is very well maintained, was comfortable for a family of five and has all of the modern amenities (air conditioning, washer/dryer, etc). Frank, the owner, was proactive reaching out and responsive to the few questions we had during our stay. Pros: gorgeous location on the beach with great snorkeling right out the back door, well equipped comfortable unit, short drive to Rum Point, great board game collection was a hit with our kids. Considerations: 30-40 minute drive from the core tourist activities (7 mile beach, shopping, etc), beach is shared with the other 5 units (although we didn’t see much of the other tenants), Wi-Fi was slow and recommend brining a good pair of water shoes as beach and much of the nearby water are a little rocky. Overall great experience! Thanks Frank!!see more
Sea Magic
Rum Point ... Sea Magic

Wonderful newly remodeled home with lots of amenities not the least of which is the huge hot tub. The house is located in a very quiet area of Rum Point yet very close to the Rum Point beach club. Would highly recommend and was very comfortable for our family of 6. … see more
Rum Sands
Woderful location

We had the perfect vacation in this condo. Great amenities available and so close to the beach. Wonderful! … see more
Kaibo Yacht Club # 29C
Nice Spot

Rum Point and the Kaibo Yacht Cub are lovely with beach, blue water, and quiet warm. The condo was perfect. Very clean and comfortable. The next door condo was being renovated so there was a lot of noise during the daytime. We found the hour long drive to town and grocery store a trek. Otherwise we enjoyed our stay on this very lovely Island.see more
The Pools #10
Just wonderful

On our first visit to Grand Cayman we could not have been more satisfied. This condo offered a very relaxing place to spend a week. The view and quiet location allowed us to forget other obligations that clutter our daily lives. The unit was clean. The kitchen fully stocked with utensils, dinnerware, dish soaps (liquid and dish washer tablets), cookware and dish towels. We did run out of coffee filters and I can not say if they are provided or if they were left over from previous guests. All other linens were provided including beach towels. No laundry soap was provided. A highlight was the indoor pool which we used daily. Our group of two couples could frequently be heard commenting on how much we enjoyed the outdoor living space created by the 2 story screened pool enclosure. It is here that we had our morning coffee and breakfasts. The beauty of tropical sand and water just outside the door was intoxicating. The unit is a short walk from Star Fish Point so we were privileged to observe star fish also living around the dock just outside the back door. Two outdoor chairs and two lounging chairs were provided if one chose to relax by the condo. We found WIFI worked best later in the evening. Check-in and check-out were convenient as the office is located very close to the airport. We were easily able to access the office with a simple phone call for any questions that arose. Rum Point Beach is a few minutes away by car. Here you will find a public beach with chairs, food, drinks, dive shop, hammocks, gift shop and a good restaurant for dinner. Also within a short walking distance of the condo is Kaibo restaurant. We found only 1 of our 3 meals there up to our expectations. Lunch food was satisfactory. Both the Tuesday evening BBQ and Luna Del Mar dinner (only happens on full moon), quality did not match the expensive cost. We would have enjoyed some sort of book in the unit with dining recommendations and things to do. We were however able to talk with other visitors for their recommendations. Our favorite dining highlights were Rum Point for dinner, the Lighthouse, Over the Edge, Morgan's Seafood. Other than going to the beach our favorite activities were boat to snorkel and Sting Ray City, Crystal Cave and Bio-luminescent tour at night.see more

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