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Holiday houses in North Side

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Top-rated holiday rentals in North Side

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Top Guest favourite
Home in North Side
4.99 out of 5 average rating, 116 reviews

North Side Grand Cayman Beachfront Villa

Spacious beachfront home on Grand Cayman’s peaceful North Side. Walk out to crystal-clear water for snorkeling and paddleboarding — we provide kayaks, paddleboards, and snorkel gear. 4 en-suite bedrooms plus two sofa beds in living room, rooftop with ocean views, fast WiFi, full kitchen, and washer/dryer. Small grocery store and Over the Edge are 1 mile away. Supermarket in Savannah (~20 min). Restaurants & bars @ Kaibo & Rum Point (~15 min). Travel crib and kids’ games available. Self check-in.

Top Guest favourite
Cottage in West Bay
4.99 out of 5 average rating, 408 reviews

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of award winning island style cottages. This unit has a private outdoor dining and garden shower. At Botanica, our focus is on casual luxury, dreamy details and high end amenities. Property highlights includes a resort style pool with heated spa set in a tropical oasis. We also offer a complimentary shuttle in our vintage Land Rover Defender to nearby beaches. Be sure to check out our other listings under my profile. Non Smoking Complex

Top Guest favourite
A private pool is framed by a wooden deck, offering views of the Caribbean Ocean. Bright blue lounge chairs are positioned nearby, alongside palm trees swaying in the gentle breeze. The turquoise water of the ocean contrasts with the sandy beach in the background.
Home in Rum Point
5 out of 5 average rating, 18 reviews

No Big Ting - Private Beach Home

Entering No Big Ting you're immediately greeted with stunning views of the beautiful Caribbean Ocean. It's all about outdoor living, from the spacious screened porch to the soft sandy beach. Cool off in the private pool or adventure out to the protected reef to snorkel with the abundant sea life. End a perfect day star gazing on the deck listening to the waves under the moonlight. No Big Ting delivers a tranquil ocean vibe and is the ultimate beachfront oasis to relax with family and friends.

Top Guest favourite
Cottage in East End
4.98 out of 5 average rating, 124 reviews

Hidden Gem Cottage on the Beach

Hidden Gem is a Traditional Cayman Style cottage located at Grapetree Cove on a beautiful beach area in sleepy fishing village of East End. The property is filled with trees that gives it a dreamy Island ambiance. The Cottage has been fully renovated with modern amenities that makes is very comfortable and homey. Hidden Gem offers a unique CaymanKind experience from a Caymanian host that knows the area well. Located minutes away from local dinning places and many key attractions in the area.

Top Guest favourite
The entrance features a dark front door framed by two windows with black shutters. Potted plants are positioned on either side of the door, adding greenery to the wooden facade. The porch is supported by two white columns, creating a welcoming appearance.
Apartment in Savannah
4.99 out of 5 average rating, 136 reviews

Enoe’s Escape

Welcoming 1 bedroom apartment with en-suite bathroom, sitting area, full kitchen, washer, dryer, and outdoor patio. Located in a quiet neighbourhood in close proximity to most things. 2-minute walk to the historic site Pedro St. James Castle, a stunning spot to view sunsets! 3-minute drive from the nearest supermarket and local restaurants. 5-minute drive to the picturesque Spotts Beach. 20-minute drive from other popular destinations, including shopping centres and other local attractions.

Top Guest favourite
Home in Rum Point
4.95 out of 5 average rating, 39 reviews

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)

Top Guest favourite
A cottage exterior is presented with a coral and green color scheme, surrounded by a landscaped yard with gravel pathways. The screened porch offers views of the inviting outdoor space, while lush greenery and palm trees enhance the peaceful atmosphere.
Cottage in East End
4.99 out of 5 average rating, 121 reviews

Piece of Mine, Beachfront Villa #3

Private & Tranquil BEACHFRONT Cottage offers all the conveniences of a luxury home. KAYAKS and SNORKELING GEAR, daybed & smart TV on the SCREENED PORCH, beach chairs, beach swing, and beautiful SUNSETS. Hammocks are throughout the property. Modern walk-in Shower, Towels, and bathrobe. Full Kitchen, Keurig & regular coffee maker & Blender, Extra-large bedroom, Caribbean Antique four-post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

Guest favourite
An outdoor terrace features comfortable wicker seating, complemented by colorful cushions. Lush palm trees frame the view of the tranquil turquoise waters and clear sky, enhancing the inviting coastal atmosphere.
Home in George Town
4.94 out of 5 average rating, 107 reviews

Paradise Beach House in South Sound, George Town

Paradise Beach House in South Sound, George Town Paradise Beach House is a beautiful vacation rental property located in South Sound, George Town, Grand Cayman. The house offers a spacious and luxurious living experience with its very own paradise beach and a view of the reef and famous wreck of South Sound! Please note the "Resort Fee" is the Government Tourist Tax that is charged to all international guests staying in the Cayman Islands.

Top Guest favourite
Home in Rum Point
5 out of 5 average rating, 18 reviews

Waterfront 2BR with private screened pool

Unwind in this renovated waterfront 2BR at Pools of the Kai, featuring a private screened pool and two king suites with water views. The upper suite has a private balcony, while the lower opens directly onto the pool deck. A sofa bed accommodates 2 additional guests. Walk to Kaibo, kayak to Starfish Point or explore Bioluminescent Bay. Fast Wi-Fi and peaceful Cayman Kai surroundings make it ideal for couples, families and groups of up to 6.

Superhost
Home in North Side
4.84 out of 5 average rating, 73 reviews

Beautiful 3 Bd Beachfront Home North Side Sleeps 7

Welcome to Azure Breeze #6, a recently renovated beachfront property. This stunning 3-bedroom, 2-bathroom home, nestled within a small 6-unit complex, invites you to embark on an unforgettable vacation in the Cayman Islands. Located on the northern coast of Grand Cayman, Azure Breeze offers convenient proximity to Crystal Caves, Rum Point, and Cayman Kai, ensuring access to a variety of exciting adventures.

Guest favourite
Apartment in Grand Cayman
4.95 out of 5 average rating, 55 reviews

Cora at The Grove Luxury One-Bedroom Apartment

The one-bedroom suite at Cora at the Grove offers refined island elegance with generous living space, designer furnishings, and a private balcony overlooking our beautiful garden. Ideal for couples or solo travelers, the suite features a fully equipped kitchen, spa-inspired bathroom, and access to all resort-style amenities including the rooftop pool and personalized concierge services.

Top Guest favourite
A clear view of a private pool surrounded by a spacious deck is presented, with the ocean visible in the background. Palm trees sway gently in the breeze, and shaded seating areas are positioned nearby, enhancing the serene atmosphere of this beachfront location.
Home in Grand Cayman
4.98 out of 5 average rating, 85 reviews

BeachPlumVilla

Snorkelers Beachfront Paradise. This private, well appointed beachfront villa has unhindered sea views, a large deck with pool, is located in a very private section of grand Cayman near Rum Point. Excellent snorkeling right off the beach and a bright and airy house with all amenities. - Please note all rates are EXCLUSIVE of Cayman Islands Dept of Tourism 13% tax.

Popular amenities for North Side holiday rentals