Book Holiday Homes in North Side

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Featured Holiday Homes in North Side

The peace and tranquility of this cottage Works Wonders on the soul....

The peace and tranquility of this cottage Works Wonders on the soul....

Grand Cayman
With a stay at this vacation home in East End, you'll be on the beach, just steps from Grand Cayman Beaches and a 3-minute drive from Mastic Trail South ...
Opens in a new windowThe peace and tranquility of this cottage Works Wonders on the soul....
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

North Side, North Side
When you a stay at this villa in North Side, you'll be on the beach, just steps from North Sound and Grand Cayman Beaches.
Opens in a new windowRum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Cayman Islands
With a stay at this vacation home in North Side, you'll be on the beach, just a 1-minute walk from North Sound and 15 minutes by foot from Grand Cayman ...
Opens in a new windowReef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
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BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
Located in North Side, this vacation home is by the ocean, within a 15-minute walk of Grand Cayman Beaches and North Sound.
Opens in a new windowBEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Coco Kai Beach Front Villa with Heated Pool and Private Dock

Coco Kai Beach Front Villa with Heated Pool and Private Dock

North Side
When you stay at this vacation home in North Side, you'll be on the beach, within a 15-minute walk of Grand Cayman Beaches and North Sound.
Opens in a new windowCoco Kai Beach Front Villa with Heated Pool and Private Dock
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Rum Point
When you a stay at this vacation home in North Side, you'll be on the beach, within a 5-minute walk of North Sound and Grand Cayman Beaches.
Opens in a new windowThe Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Relax at Coconut Bay!

Relax at Coconut Bay!

West Bay
With a stay at this vacation home in West Bay (Northwest Point), you'll be within a 10-minute drive of Seven Mile Beach and Cayman Motor Museum.
Opens in a new windowRelax at Coconut Bay!
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

Grand Cayman
Located in North Side, this vacation home is on the beach, within a 5-minute walk of North Sound and Grand Cayman Beaches.
Opens in a new windowSEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

2 out of 5
North Side
When you stay at this vacation home in North Side, you'll be on the beach, within a 5-minute drive of Grand Cayman Beaches and North Sound.
Opens in a new windowAzure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

North Side Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our North Side vacation homes are the perfect way for you to wing it.

Holiday houses in North Side let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of North Side in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local North Side adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in North Side with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of North Side vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

North Side Holiday Homes essential information

Accommodation
253 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The peace and tranquility of this cottage Works Wonders on the soul...., Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes., Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, Coco Kai Beach Front Villa with Heated Pool and Private Dock, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Relax at Coconut Bay!, SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point , Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Top trending hotels in North Side

Ocean Paradise

Ocean Paradise

4 out of 5
1234 Rum Point Road, North Side, Grand Cayman
Located in North Side, Ocean Paradise is by the ocean, a 1-minute drive from North Sound and 8 minutes from Starfish Beach.
Opens in a new windowOcean Paradise
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
Located in North Side, this vacation home is by the ocean, within a 15-minute walk of Grand Cayman Beaches and North Sound.
Opens in a new windowBEACHFRONT w/ Private Dock-50 ft Pool-Theatre
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

Grand Cayman
Located in North Side, this vacation home is on the beach, within a 5-minute walk of North Sound and Grand Cayman Beaches.
Opens in a new windowSEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Save an average of 15% on thousands of hotels when you're signed in
Coco Kai Beach Front Villa with Heated Pool and Private Dock

Coco Kai Beach Front Villa with Heated Pool and Private Dock

North Side
When you stay at this vacation home in North Side, you'll be on the beach, within a 15-minute walk of Grand Cayman Beaches and North Sound.
Opens in a new windowCoco Kai Beach Front Villa with Heated Pool and Private Dock
Don't see what you're looking for?
See all available properties in North Side
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.