Vacation rentals in North Side

4.98 out of 5 average rating, 47 reviews

A bright exterior of a two-story villa is highlighted by vibrant yellow walls and large windows. Lush tropical plants surround the property, framing the entryway. A screened-in porch offers a cozy atmosphere. The setting features abundant natural light under a clear blue sky.

Villa in Old Man Bay

Affordable Old Man Bay Villa #2

Tucked away in a corner of Northside, Grand Cayman, is the quaint little community of Old Man Bay, where time has stood still. This is the authentic Cayman, no crowds and the only thing you'll hear are the ocean waves. The 2 side-by-side 1 bedroom villas are identical in layout. The main floor has a living room with queen size sofa bed, flat screen TV, fully equipped kitchen with Dishwasher & powder room. The spacious bedroom is on the 2nd floor and has a full ensuite with a large shower.

5 out of 5 average rating, 19 reviews

Home in North Side

Nature lovers paradise newly renovated

A true tropical nature lovers dream on the North Side of the island. Relax with the whole family at this peaceful, newly renovated house surrounded by fruit trees and rock paths. If your travel is for romance, business, or family vacation, it's all covered here. Located across the street from the beach and close to restaurants, supermarketsand the famous Rum Point Club and Kaibo Yacht Club. Minutes from attractions such as the Cayman Crystal Caves, Queen Elizabeth ll Botanic park, Starfish Point

4.99 out of 5 average rating, 88 reviews

Home in North Side

Ocean's Edge: Beachfront Home with Rooftop Views

Oceanfront property with beauty all around. Walk out your door into crystal clear water. Snorkeling, paddle boarding, kayaking, and more can be experienced steps away from your beachfront home. Nearby are grocery stores, restaurants, bars, as well as the famous attraction the Cayman Crystal Caves. The house is bright and full of space. 4 bedrooms all have attached bathrooms. YOU WILL NOT FORGET THE ROOFTOP. Plenty of outdoor furniture to sit back, relax, and enjoy the views from Ocean's Edge

4.96 out of 5 average rating, 50 reviews

Home in North Side

Oceanfront Dreamsicle Villa w/Outdoor Living Area

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.

4.87 out of 5 average rating, 15 reviews

A selection of eco-friendly toiletries is displayed on sandy beach. Four blue, textured bottles labeled 'Purely' house shampoo, conditioner, and body wash. A white bar of soap sits among the bottles, accompanied by a small starfish, creating a serene coastal vibe.

Apartment in North Side

Apartment in Frank Sound

Welcome to our home!! Situated in Frank Sound, North Side. This apartment provides accommodation with free private parking. Small apartment attached to the main house, for added privacy, the accommodation features a private entrance. One room with 1 small closet and with one bathroom and kitchen with utensils. The apartment includes TV, wifi, hot water, beach chairs, cooler and much more! A short drive to tourist attractions; Kaibo, Rum Point, Crystal Caves, Blow holes & Barefoot beach.

4.91 out of 5 average rating, 45 reviews

Spacious 2-Bedroom 2-Bathroom Beachfront Condo wit

The two 2-bedroom condominium located in Old Man Bay on the North Side of Grand Cayman is nestled in a prime oceanfront location. Step into this expansive unit boasting over 1,685 sq ft of living space, including a generously sized balcony that offers panoramic and uninterrupted vistas of the magnificent Caribbean Sea. Immerse yourself in the breathtaking views not only from the balcony, but also from the comfort of the living room and kitchen, creating a truly mesmerizing experience.

4.98 out of 5 average rating, 123 reviews

The exterior of the villa is showcased from across the water, featuring a light-colored structure with a sloped roof. Lush palm trees frame the view, and a sandy area leads to the water's edge, creating a tranquil atmosphere in the natural surroundings.

Apartment in KY

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.

4.94 out of 5 average rating, 140 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!

An aerial view captures the beachfront condo surrounded by lush greenery, with a clear swimming pool visible beside the unit. Sun loungers line the sandy shore, and a thatched gazebo is positioned near the water's edge, offering a tranquil setting.

4.96 out of 5 average rating, 25 reviews

*Beachfront* Coco Sands - 2 bed condo at Rum Point

*Save up to 20% off weekly stays this Fall* Relax and unwind at Coco Sands at North Pointe Condos. A newly renovated beachfront vacation condo located in Grand Cayman's tranquil North Side. Our condo is a ground floor, end unit with a large screened patio that has spectacular sea views and direct access to the beach. Every amenity is included for relaxing, dining, and enjoying the pool and beach, as well as high-speed WiFi to keep you connected when you need it.

5 out of 5 average rating, 7 reviews

A stretch of sandy beach is lined with several lounge chairs facing the water. Palm trees provide gentle shade in the background, while a pier extends into the turquoise ocean, offering a view of the expansive sky adorned with soft clouds.

Apartment in Rum Point

The Retreat at Rum Point Beach

Forget your worries in this spacious and serene space. we're located in the peaceful beauty area known for it privates, Cayman Kai, on the most pristine beach on Grand Cayman. Known for the most beautiful sunrises and sunsets. This complex is well maintained. it has its only private tennis court/Gym . You can swim/dive or snorkel outside of your door. Can rent jet ski and other such items next door. Also great food next door. One of the safest place on earth.

4.99 out of 5 average rating, 109 reviews

Cottage in East End

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, Antique four-post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

A beachfront gazebo with a thatched roof is surrounded by palm trees, swaying gently in the breeze. The sandy area leads to the calm waters, showcasing the serene atmosphere of the property. A portion of the building is visible to the right.

5 out of 5 average rating, 31 reviews

Beachfront Kaibo Condo

Relax with the whole family at this peaceful place to stay. Spend lazy days under the coconut palms or lounging in a hammock in the shade under the beachfront gazebo. Kaibo Brisote is just a short walk to Cayman's famous Star Fish Point and an even shorter walk down the beach to Kaibo Beach Marina, Restaurant and Bar. The perfect spot for family vacations or just a quiet get away. Come make your Cayman Islands memories with us.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for North Side vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in North Side

5 out of 5 average rating, 7 reviews

SeaBreeze Retreat 17

Yuliya KRating, 5 stars10 months ago

We had such a wonderful experience staying at Stephanie's place. She is an excellent host. Her beautiful condo is very comfortable and includes everything you need for a relaxing vacation. The location of the condo is also very convenient. There was so much to see and to do in the area. The Bioluminescence Bay and Starfish Point are a must and are almost in your backyard. We loved staying at the beach, which felt like a private beach most of the time. Thanks, Stephanie. We would love to come back and stay at your beautiful place again.

A serene beach scene features two thatched umbrellas set over white sand, accompanied by a pair of lounge chairs. A wooden dock extends into the clear turquoise water, with gentle waves under a blue sky adorned with fluffy clouds.

Villa in North Side

4.95 out of 5 average rating, 88 reviews

Coco Kai Beach Front Villa heated pool and dock

OleRating, 5 stars1 month ago

The house was great and the grandkids loved the pool and the beach. Chisholm’s grocery store made it easy to get everything we needed. Jason also arranged for one of his friends, Ben, to take us on a boat trip including snorkelling and feeding stingrays which was very reasonably priced and a big success for everybody. All in all a very good trip and we can recommend Coco Kai to anybody thinking about going to the Cayman Islands.

Lush greenery frames a sandy beach area where two lounge chairs are positioned under palm trees. The tranquil blue water of the sea is visible in the background, complemented by a clear sky and gentle waves lapping at the shore.

Villa in Rum Point

4.83 out of 5 average rating, 6 reviews

Gorgeous Sandy Beachfront at Azure Breeze Villas

ChristineRating, 5 stars78 months ago

We enjoyed our stay at Rum Point. The ocean breeze was fabulous. Beautiful and relaxing.

A serene beachfront scene showcases the clear turquoise waters gently lapping at a pristine stretch of white sand. Lush greenery is visible in the background, while a blue sky dotted with fluffy clouds creates a tranquil atmosphere, inviting relaxation and exploration.

5 out of 5 average rating, 6 reviews

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

DorothyRating, 5 stars3 weeks ago

From start to finish the host was great at communication which made everything so much easier and stress free. The condo was immaculate and had everything we needed for our week there. We were so happy that we chose this condo and location for our trip. I would highly recommend this host and any properties he may have and will definitely be booking with him again on our next trip.

A serene beachfront scene showcases soft white sand and clear turquoise waters under an expansive blue sky. Several tall palm trees gently sway in the breeze, casting delicate shadows on the sand. The horizon meets the calm sea, enhancing the tranquil atmosphere.

Apartment in Rum Point

4.88 out of 5 average rating, 8 reviews

SeaRendipity oceanfront unit. Beach & snorkeling!

EmilyRating, 5 stars22 months ago

Fabulous place! Snorkeling right out the back door. Quiet and peaceful, had everything we needed and more. It is a bit from town, if that concerns you. Was perfect for us. It was pretty warm in July, so we just stayed in the water. Starfish Point is close by. There is a small grocery store right up the road. Definitely recommend checking out On the Edge restaurant. The house had everything we needed. A very well stocked kitchen!

Superhost

A scenic view along the coastline showcases calm turquoise waters meeting a sandy beach. Palm trees gently sway in the breeze, with scattered beach rocks visible. The image captures the beauty of the oceanfront, creating a serene coastal atmosphere.

5 out of 5 average rating, 4 reviews

Silver Reef #4 / 2 BR LUXE Oceanfront w/ Pool

JessRating, 5 stars5 months ago

First of all...words cannot explain how beautiful this place truly was. If ever visiting and you want that peaceful and serene view, this is definitely the place. Don definitely made this trip worth being here by providing a list of many things to do around the island and all of the contacts. We loved everything about our visit so much we actually plan on coming back in the summer. Fingers crossed this place is available. Thanks again Don!

4.91 out of 5 average rating, 58 reviews

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, which is framed by a white gazebo. The ocean is visible in the background, complementing the tranquil setting.

Townhouse in Old Man Bay

Your Oceanside Retreat Awaits!

BarbaraRating, 5 stars3 months ago

Clean, comfortable villa with amazing views overlooking pool and beach. After a slight hiccup with broken lock on arrival, nearby property manager quickly responded and got things squared away with a new lock. We had a wonderful stay and would definitely return to this beautiful villa! Ernie’s instructions on surrounding area were spot on. We shopped at the market in Savannah on the way in from the airport and enjoyed dinners at Over the edge and Tukka. Pro tip – use the shopping carts under the stairwell when arriving with groceries and bring everything up via elevator. Thanks for a wonderful stay!

An aerial view captures a secluded beach lined with palm trees and white sand. Clear blue waters gently meet the shore, showcasing a serene environment. Beach umbrellas are visible along the shoreline, while distant buildings and tropical vegetation accentuate the landscape.