Vacation rentals in North Side

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Top-rated vacation rentals in North Side

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Guest favorite

Villa in Old Man Bay

4.97 out of 5 average rating, 32 reviews

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.

Oct 28 – Nov 4

G$32,813 GYD per night

Guest favorite

Home in North Side

5.0 out of 5 average rating, 9 reviews

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

Jul 25 – Aug 1

G$63,922 GYD per night

Guest favorite

Guest suite in Grand Cayman

4.98 out of 5 average rating, 46 reviews

Studio 1 @ Fort Rocks, Forest King near beach!

STUDIO 1 has amazing natural rock & forest views, WiFi, electricity, water, AC, King bed, seating area, dining area, SMART flat screen TV, portable induction hot plate, coffee maker, toaster oven w/air fryer, microwave, bread toaster, dishwasher, fridge/freezer, compact washer/dryer, private back patio & large two level deck (with deck net) perfect for yoga, morning coffee or just relaxing. Fire pit & BBQ grill. 1 parking space. Close to beaches, restaurants, local attractions, shops & schools.

Aug 18 – 25

G$43,541 GYD per night

Guest favorite

Condo in Rum Point

5.0 out of 5 average rating, 17 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!

Aug 22 – 29

G$63,803 GYD per night

Guest favorite

Condo in Rum Point

5.0 out of 5 average rating, 40 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.

May 14 – 21

G$76,590 GYD per night

Guest favorite

Condo in Rum Point

5.0 out of 5 average rating, 24 reviews

Tropical Paradise Cayman Kai-Vu, 2 Bed Beach Front

Our upgraded ground-floor condo is in beautiful Cayman Kai on the North end offering all the amenities of home. It is the perfect place to spend your vacation with family, friends, romance or relaxation. Screened-in porch with gorgeous ocean views and walkout beach access. Kaibo Yacht Club is right next door featuring a marina, coffee shop, beach bar with an outdoor pizza oven, upstairs fine dining restaurant and rum bar. Best of all it is away from the crowds your own private paradise!

Oct 7 – 14

G$74,232 GYD per night

Guest favorite

Apartment in KY

4.98 out of 5 average rating, 107 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.

Dec 3 – 10

G$60,017 GYD per night

Guest favorite

Condo in Rum Point

4.92 out of 5 average rating, 111 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!

Nov 7 – 14

G$96,773 GYD per night

Guest favorite

Condo in North Side

4.94 out of 5 average rating, 17 reviews

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

*Save up to 20% off weekly stays in Summer 2024* 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.

Oct 1 – 8

G$58,274 GYD per night

Guest favorite

Cottage in East End

4.99 out of 5 average rating, 94 reviews

Piece of Mine, Beachfront Villa #3

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 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!!"

Sep 20 – 27

G$79,137 GYD per night

Guest favorite

Apartment in GRAND CAYMAN

4.94 out of 5 average rating, 183 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.

Oct 26 – Nov 2

G$46,224 GYD per night

Guest favorite

Home in North Side

5.0 out of 5 average rating, 33 reviews

Private oceanfront one-level home w/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 concept. Relax on the 360 degree wraparound screened porch which has two seating areas both boasting oceanfront views of the Caribbean Sea. Over 175 ft of private oceanfront living.

Dec 2 – 9

G$108,008 GYD per night