Vacation rentals in North Side

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Top-rated vacation rentals in North Side

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Guest favorite

Place to stay in Rum Point

5 out of 5 average rating, 10 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.

Guest favorite

Condo in Rum Point

4.92 out of 5 average rating, 25 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!

Guest favorite

Home in North Side

4.95 out of 5 average rating, 40 reviews

Oceanfront “Dreamsicle” Villa with Kayaks

Oceanfront “Dreamsicle” Villa is a 3 bedroom/3 bath vacation getaway located on Northside of Grand Cayman. The ocean is a few steps from the back door. Mahogany Point is a secluded beach front property and you'll enjoy sunshine in this tranquil location. The amazing view of the Caribbean Ocean from the master bedroom balcony; community pool, gazebo, lounge chairs, stocked kitchen, new appliances, granite countertops, and WiFi. Outdoor charcoal Weber grill located in private Villa courtyard.

Guest favorite

Condo in Rum Point

5 out of 5 average rating, 46 reviews

Seaside Serenity at Cayman Kai

Forget your worries in this spacious and serene space. Kaibo Yacht Club Phase II is a small, 30-unit complex on the quiet side of Grand Cayman. Guests love the peacefulness of Cayman Kai, located on the opposite side of the island from Seven Mile Beach. A rental car is strongly recommended to fully appreciate island-wide attractions and to enjoy the many restaurants. Kaibo Restaurant, next door, offers many options. If you are a legal resident advise us at booking for tourist tax waiver.

Guest favorite

Vacation home in Bodden Town

5 out of 5 average rating, 85 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,

Guest favorite

Rental unit in KY

4.97 out of 5 average rating, 113 reviews

Rum Haven villa on Bioluminescent Bay & Ocean view

Rum Haven is located at 75 Sand Point Road in the beautiful, tranquil district of North Side, across the street from the world famous Rum Point Club. 10 minutes by boat to Stringray City with the Bioluminescent at the end of the cove by this unit. Kaibo Yacht club is located 1 mile away with the beautiful Crystal Caves and Botanic Park only 7 miles away. Kayak and hammocks available for guests to use. The Red/Orange kayak belong to Rum Haven and the paddles are on the screen porch.

Guest favorite

Condo in Rum Point

4.94 out of 5 average rating, 18 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.

Guest favorite

Condo in Rum Point

4.93 out of 5 average rating, 123 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!

Guest favorite

Home in North Side

5 out of 5 average rating, 36 reviews

Private oceanfront home wraparound screened porch

Breezy Bay is an oceanfront, private, single-level 3 bedroom home in North Side (Old Man Bay) perfect for your relaxing Grand Cayman vacation. Enjoy panoramic oceanfront views from this beach house with a bright, open air concept. Relax on the 360 degree wraparound screened porch which has two seating areas both boasting oceanfront views of the Caribbean Sea. Direct water access into the sea. Separate primary suite for ultimate privacy. Located on 1+ acres. Free kayaks.

Guest favorite

Home in North Side

4.83 out of 5 average rating, 48 reviews

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

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day.

Guest favorite

Rental unit in GRAND CAYMAN

4.93 out of 5 average rating, 201 reviews

Rum Cove on the Bioluminescent Bay with Ocean View

Beautiful Rum Cove is located next to two one bedroom Villas and it's nicely decorated to suit our Island living, which is quiet and friendly to all who come to live amounts us. Rum Cove sit's in the beautiful Cove where the famous Bioluminescent Bay sits in your backyard. We welcome you to Rum Cove and want to offer you our Cayman Kind. Rum Point Beach Bar and Fine Dining Restaurant is located across the street from Rum Cove.

Superhost

Villa in Old Man Bay

4.89 out of 5 average rating, 54 reviews

Old Man Bay Villa #1

Old Man Bay is a quaint little cluster of homes and a church on the north side of the island. This idyllic setting, with no crowds and no noise, allows for an authentic island experience and what you've come to Cayman for: Peace, quiet and tranquility. Please Note: OUR PRICES INCLUDE THE 13% ACCOMMODATION TAX.