Book Holiday Homes in North Side

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in North Side

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
Book a stay at this beach vacation home in North Side. Enjoy private pools, a beach locale, and a garden. Popular attractions Grand Cayman Beaches and Cayman ...
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes

Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes

Rum Point
Book a stay at this beach vacation home in North Side. Enjoy a beach locale, a water park, and patios. Popular attractions Stingray City and Rum Point Beach ...
Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes
Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock

Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock

East End
Book a stay at this beach vacation home in East End. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Colliers Public Beach and East End ...
Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock
Save an average of 15% on thousands of hotels when you're signed in
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
Stay at this vacation home in George Town. Enjoy free WiFi, a garden, and patios. Popular attractions Port of Georgetown and Seven Mile Beach are located ...
Slice of Paradise- 2 mins from Spotts Beach!
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
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Cayman Kai Public Beach and Star ...
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas

Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas

North Side
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Mastic Trail North Trailhead and Grand ...
Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas
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
Book a stay at this beach vacation home in East End. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Queen Elizabeth II Botanic Park ...
The peace and tranquility of this cottage Works Wonders on the soul....
Ocean's Edge: Beachfront Home with Rooftop Views

Ocean's Edge: Beachfront Home with Rooftop Views

North Side
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and patios. Popular attractions Mastic Trail North Trailhead and Babylon ...
Ocean's Edge: Beachfront Home with Rooftop Views
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

Grand Cayman
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Stingray City and Cayman ...
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
Don't see what you're looking for?
See all available properties in North Side
View all properties
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
208 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes, Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock, Slice of Paradise- 2 mins from Spotts Beach!, Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas, The peace and tranquility of this cottage Works Wonders on the soul...., Ocean's Edge: Beachfront Home with Rooftop Views, So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

Top trending hotels in North Side

Moon Glow DREAMY 2BR OCEANFRONT VILLA WITH PRIVATE BEACH, Kayak, Snorkeling

Moon Glow DREAMY 2BR OCEANFRONT VILLA WITH PRIVATE BEACH, Kayak, Snorkeling

Rum Point
Book a stay at this beach villa in North Side. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cayman Kai Public Beach and Rum Point Beach ...
Moon Glow DREAMY 2BR OCEANFRONT VILLA WITH PRIVATE BEACH, Kayak, Snorkeling
Ocean Paradise

Ocean Paradise

4 out of 5
1234 Rum Point Road, North Side, Grand Cayman
Stay at this 4-star beach vacation home in North Side. Enjoy free WiFi, free parking, and a garden. Popular attractions Cayman Kai Public Beach and Star Fish ...
Ocean Paradise
On The Bay

On The Bay

4 out of 5
67 Old Robin Rd, North Side, North Side
Stay at this 4-star beach condo in North Side. Enjoy free WiFi, free parking, and private pools. Popular attractions Babylon (Dive Site) and Mastic Trail North ...
On The Bay
Save an average of 15% on thousands of hotels when you're signed in
FAR TORTUGA: Luxury Beachfront Villa w/ Heated Pool and Private Snorkeling Dock

FAR TORTUGA: Luxury Beachfront Villa w/ Heated Pool and Private Snorkeling Dock

2 out of 5
North Side
Book a stay at this beach villa in North Side. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Mastic Trail North Trailhead and Grand ...
FAR TORTUGA: Luxury Beachfront Villa w/ Heated Pool and Private Snorkeling Dock
Don't see what you're looking for?
See all available properties in North Side
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.