Holiday rentals in North Side

5 out of 5 average rating, 26 reviews

A modern two-story home features expansive glass doors and large windows that provide views of the outdoor space. A private pool and putting green are surrounded by lush landscaping, creating a refreshing environment. Lounge chairs are positioned nearby for relaxation.

Home in North Side

Luxury Beachview Retreat, Cayman Island.

Luxurious, four bedroom, four and a half bath home with ensuite bathrooms and a half bath for guest. All bedrooms provide a private balcony with stunning oceanviews. This modern gated home in Northside is only 40mins from the airport and features a private pool, public beach access and a mini-golf course. BEDS Master on upper level has a king bed Second bedroom on upper level has a queen bed Third bedroom on upper level has 1 full bed and 3 twins Fourth bedroom on lower level has a queen bed.

A vibrant view of the Caribbean Sea showcases varying shades of blue, blending into the horizon. Palm trees frame the sandy beach below, alongside the light-colored buildings of The Sea Biscuit Cottage, inviting relaxation in a tropical setting.

5 out of 5 average rating, 39 reviews

Sea Biscuit 1BR Oceanfront at The Sea Lodges

Welcome to Sea Biscuit at The Sea Lodges, a charming direct beachfront retreat in Rum Point, Cayman Kai. This cozy 1-bedroom, 1-bathroom hideaway sits along a peaceful stretch of the Caribbean coastline, perfect for those seeking both relaxation and adventure, 1/4 mile from Rum Point. Just a 5-minute walk from Rum Point Beach, you'll find incredible snorkelling right offshore. Explore a vibrant underwater world of tropical fish, sea creatures, conch, and healthy coral reefs – perfect for snork

5 out of 5 average rating, 6 reviews

Flat in Rum Point

Rum Point Retreat | Your island escape

Enjoy this spacious 1 bed, 1 bath short-term rental at The Retreat at Rum Point, Grand Cayman. The large lounge room offers stunning views of the Caribbean Sea, perfect for relaxing or entertaining. The open layout is filled with natural light, highlighting the beautiful sea scenery. Located close to Rum Point’s pristine beaches and crystal-clear waters, this retreat is ideal for a peaceful, scenic getaway in paradise. Comfortable, modern, and conveniently situated for a memorable Caribbean stay

4.93 out of 5 average rating, 223 reviews

A screened-in patio features a colorful area rug and seating arrangement with patterned cushions. A ceiling fan is visible above, while views of the lush garden and cove are framed by large glass panels. Kayaks and lounge chairs are positioned outside, enhancing the outdoor atmosphere.

Flat in Cayman Kai

Rum Cove on the Bioluminescent Bay with Ocean View

Welcome to Rum Cove – your private escape on the bioluminescent bay, just steps from the world-famous Rum Point. This bright & breezy 1-bedroom retreat is part of a charming triplex and offers stunning 360° views. Whether you’re relaxing on the patio, kayaking under the stars, or sipping coffee at sunrise, Rum Cove surrounds you with natural beauty & peace. A perfect space for couples, solo travelers or small families looking for a quiet getaway with the best of Cayman Kai on your doorstep.

Place to stay in Rum Point

An expansive infinity pool reflects swaying palm trees under a sunset sky. Lounge chairs are arranged along the poolside, inviting relaxation by the water. The serene atmosphere is enhanced by the soft colors of the sky and the tranquil water's surface.

5 out of 5 average rating, 27 reviews

Yippee Kai Yay Beachfront oasis

Welcome to Yippee Kai Yay /Kaibo Sunset - Unit B17! Situated within the prestigious development of Cayman Kai, where us locals go to unwind and relax ,Kaibo Sunset is the premiere vacation getaway in Grand Cayman with fun and activities at your fingertips! For the water enthusiast, it is paradise, with soft white sandy beaches fringed with coconut and royal palms intermixed with carefully chosen tropical plants ,a beautiful infinity pool and hot tub for the true Cayman Caribbean experience.

A sandy beach is framed by tall palm trees, with a relaxing hammock suspended between them. Two lounge chairs are positioned nearby, offering a peaceful spot to enjoy the ocean view, while calm waters stretch into the distance under a clear blue sky.

4.96 out of 5 average rating, 46 reviews

"Mai Kai" Recently renovated Oceanfront Condo

“Mai Kai” is a beautiful renovated 2 bedroom, 2 bathroom oceanfront condo at Kaibo Yacht Club II, in the heart of the Cayman Kai community. At ground floor level you have direct easy access to the gorgeous beach through the private screened outdoor patio. Steps away is the large pool and hot tub to laze away the days, two Kayaks are also included for your use and enjoyment. So whether you are seeking a romantic getaway or a family fun filled vacation "Mai Kai" and surroundings will deliver!

Holiday home in Bodden Town

A serene view of the turquoise ocean stretches beyond a well-maintained pool area. Lush palm trees and vibrant greenery frame the space, with a sandy beach visible nearby. The outdoor seating area is partially shaded, creating a relaxing atmosphere for guests.

5 out of 5 average rating, 104 reviews

Art Beach House, boutique style luxury.

Private getaway for couples or singles perfect for honeymooners situated at beautiful frank sound. 25 mins from George town so car essential, many attractions nearby include the crystal caves 5 mins botanical gardens and rum point, and the beautiful east end. we also boast some of the the best dining on island. So lots to do or just chill on your private beach away from the crowds. the apartment is situated on ground floor level with art studio/Gallery above. with exclusive use of pool,

4.94 out of 5 average rating, 31 reviews

Home in Rum Point

Whispering Kai: beach home on Bio Bay, Cayman Kai

A quiet oasis with unforgettable views. Located directly on the Bioilluminesce Bay in the wonderful residential area of Cayman Kai is our luxurious yet comfortable 2 bedroom, 2 bathroom secluded beachfront home complete with a spacious screened-in back patio overlooking the water on a white sandy beach with a private boat dock. Check us out on Insta: @whisperingkai Master Bedroom: King Bed Guest Bedroom: King Bed plus two pull-out sofas (twins) Living Room: One pull-out sofa (double)

A screened-in covered patio features a wicker hanging chair and a sofa adorned with light cushions. Large glass doors provide unobstructed views of palm trees and the beachfront, while vibrant flowers add a touch of color to the tranquil space.

4.95 out of 5 average rating, 39 reviews

Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot

Nestled in the heart of serene and picturesque Cayman Kai, welcome to Jelly Kai, Unit A9, a 2 bedroom 2 bathroom beachfront condo located at Kaibo Yacht Club Phase 2. As you step into this recently renovated second-floor condo, you'll immediately feel the tranquil ambiance that the Cayman Kai area is renowned for. The condo's recent and meticulous renovation (Summer 2023) spared no expense, creating a welcoming retreat that will ensure that you and your family feel right at home.

An outdoor dining area is presented under a vibrant teal umbrella, featuring a glass-top table surrounded by several green chairs. The view beyond includes sandy beach and the Caribbean Sea, framed by palm trees and coastal vegetation.

4.94 out of 5 average rating, 158 reviews

Nature's View: Pools of the Kai #2

Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!

5 out of 5 average rating, 19 reviews

A serene beachfront scene features clean white sand gently sloping to a clear turquoise sea. Lush palm trees provide shade along the shore, while a rocky outcrop is visible in the water. Beach chairs are arranged invitingly, offering views of the tranquil coastline.

Flat in North Side

On The Bay 310 - Enjoy the View

Pristine beachfront condo with large bedrooms and master bath. On the Bay is one of the nicest condo complexes on the Northern Coastline of Grand Cayman. It has beautiful and lush tropical landscaping, which is maintained daily, and a beautiful beach located in a cove directly in front of the apartment complex with clean white sand. Enjoy the large pool and cabana with BBQ area for your convenience. Restaurants, diving, water sports and grocery stores are a 10 min drive away.