North Side holiday rentals

We found 1,330 holiday rentals — enter your dates for availability
Select from 111 houses, 135 flats and other holiday rentals to find the perfect place for your stay in North Side. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, including air conditioning and cable TV. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – North Side

Showing deals for:27 Nov - 4 Dec

Enjoy your vacation and all Kaibo has to offer in relaxed surroundings!
Stroll the beach to the neighboring Kaibo restaurant, bar & coffee shop.
"Mai Kai' decor truly emphasizes the relaxed island vibe!
Just steps away is the large salt pool to relax in and unwind!
Exceptional
(61 reviews)

"Mai Kai" Recently renovated Oceanfront Ground Floor Condo - Kaibo Yacht Club II

North Side

16% off
S$2,905
for 7 nights, 1 apartment
S$415 per night
includes taxes & fees
"Mai Kai" Recently renovated Oceanfront Ground Floor Condo - Kaibo Yacht Club II
Pool
Beach
Kitchen with huge island.
Most amazing rooftop.
Exceptional
(68 reviews)

7 Mile Luxury Beach Club. Ocean views from Roof Terrace and Pool Pavilion.

West Bay

5% off
S$17,811
for 7 nights, 1 apartment
S$2,544 per night
includes taxes & fees
7 Mile Luxury Beach Club. Ocean views from Roof Terrace and Pool Pavilion.
Pool in the Courtyard just steps away from the door
Outdoor dining
Exterior
Great for Little Kids!
Exceptional
(46 reviews)

Beachfront Walkout Condo - Seven Mile Beach - Quiet/Away from Resort Crowds

Seven Mile Beach

8% off
S$4,270
for 7 nights, 1 apartment
S$610 per night
includes taxes & fees
Beachfront Walkout Condo - Seven Mile Beach - Quiet/Away from Resort Crowds
Ocean and pool (to the right) just a few steps from bedroom patio
Pool and beach are less than 30 steps away
What a view!
Open beautiful garden and ocean view
Exceptional
(111 reviews)

Cayman White Sand Beach + Quiet Pool = Relaxation

West Bay

8% off
S$3,505
for 7 nights, 1 apartment
S$501 per night
includes taxes & fees
Cayman White Sand Beach + Quiet Pool = Relaxation
Living area
Exterior
Room
Pool
Exceptional
(51 reviews)

Seven Mile Beach -2nd Floor Beach View at Sunset Cove

Seven Mile Beach

8% off
S$5,189
for 7 nights, 1 apartment
S$741 per night
includes taxes & fees
Seven Mile Beach -2nd Floor Beach View at Sunset Cove
The Pool
Beach
Expansive Kitchen Island
Dining
Exceptional
(5 reviews)

7 Mile Beach Condo with Pool View and Rooftop

West Bay

8% off
S$17,098
for 7 nights, 1 apartment
S$2,443 per night
includes taxes & fees
7 Mile Beach Condo with Pool View and Rooftop
Room
Property grounds
Exterior
Private kitchen
Exceptional
(17 reviews)

Beautiful one bedroom apartment

Bodden Town

8% off
S$1,622
for 7 nights, 1 apartment
S$232 per night
includes taxes & fees
Beautiful one bedroom apartment
Calm bedroom. Blackout curtains. Queen bed.
SEVEN MILE BEACH. Lots of eateries and bars along the length.
In front of Suite 4 / Dedicated parking space
Dedicated parking space
Exceptional
(30 reviews)

S4 BP | Steps to Beach | Save 15% if Book Non-Refundable

West Bay

11% off
S$2,210
for 7 nights, 1 apartment
S$316 per night
includes taxes & fees
S4 BP | Steps to Beach | Save 15% if Book Non-Refundable
Pool
Living area
Property grounds
Private kitchen
Exceptional
(17 reviews)

Modern Condo - Seven Mile Beach - Cayman Islands - Walk Everywhere

Seven Mile Beach

8% off
S$7,546
for 7 nights, 1 apartment
S$1,078 per night
includes taxes & fees
Modern Condo - Seven Mile Beach - Cayman Islands - Walk Everywhere
View from beach
View from screened lanai over beach and cove
Pool looking out over dock and Cove.
Private kitchen
Exceptional
(152 reviews)

Dream Kai -Island House #15

North Side

8% off
S$4,088
for 7 nights, 1 home
S$584 per night
includes taxes & fees
Dream Kai -Island House #15
View of the primary bedroom and balcony
The middle pool at the Wyndham Resort. Here's where you'll find the kiddies pool
Another view of the beach bar
Castaways' Cove Pool and hot tub
Exceptional
(25 reviews)

East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!

East End

8% off
S$3,550
for 7 nights, 1 apartment
S$507 per night
includes taxes & fees
East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!
Beach hop to nearby Rum Point
...with an infinity pool...
...or marvel at the beauty of native plants in the nearby botanical garden
Prepare your morning coffee overlooking tranquil waves
Exceptional
(95 reviews)

Beachfront 1st Floor Condo - Step off your patio and into paradise!

East End

8% off
S$3,766
for 7 nights, 1 apartment
S$538 per night
includes taxes & fees
Beachfront 1st Floor Condo - Step off your patio and into paradise!
Beach
Interior
Interior
Room
Exceptional
(24 reviews)

Luxury Designer Seven Mile Beachfront Condo Townhouse -Direct Walk-out to Beach!

Seven Mile Beach

8% off
S$12,295
for 7 nights, 1 apartment
S$1,756 per night
includes taxes & fees
Luxury Designer Seven Mile Beachfront Condo Townhouse -Direct Walk-out to Beach!
View from inside
Beach
Kaibo beach bar and restaurant
Pool
Exceptional
(110 reviews)

Beautiful Beachfront Condo in Cayman Kai/Rum Point

North Side

8% off
S$2,990
for 7 nights, 1 apartment
S$427 per night
includes taxes & fees
Beautiful Beachfront Condo in Cayman Kai/Rum Point
Beach
Living area
Interior
Living area
Exceptional
(68 reviews)

Escape to Paradise – Beautiful & Budget-Friendly Condo!

North Side

8% off
S$2,954
for 7 nights, 1 apartment
S$422 per night
includes taxes & fees
Escape to Paradise – Beautiful & Budget-Friendly Condo!
Dining
Interior
Pool
Private kitchen
Exceptional
(35 reviews)

Ocean/Beachfront - stunning views! Seabreeze Villas

Bodden Town

8% off
S$4,678
for 7 nights, 1 apartment
S$668 per night
includes taxes & fees
Ocean/Beachfront - stunning views! Seabreeze Villas
on site Diving Facilities
Great views and sunsets from our private beach
1st floor view from kitchen
Full kitchen
Exceptional
(64 reviews)

Coconut Bay-Cayman Divers Delight...END UNIT with Extra Living Space/Windows

West Bay

8% off
S$4,818
for 7 nights, 1 apartment
S$688 per night
includes taxes & fees
Coconut Bay-Cayman Divers Delight...END UNIT with Extra Living Space/Windows
Our private beach and water access
Pool
The Entrance
Dining
Exceptional
(38 reviews)

Relax at Coconut Bay!

West Bay

8% off
S$4,510
for 7 nights, 1 home
S$644 per night
includes taxes & fees
Relax at Coconut Bay!
Yes!, That is a queen-size pull-out sofa bed in the living area.
Living area with floor to ceiling sliding doors.
Bedroom has King size bed, two closets, and black out curtains.
Balcony includes dining table, loungers, and drying racks.
Exceptional
(8 reviews)

LUXURY/OVERSIZED - 1 Bed/1.5 Bath near AMAZING SHORE DIVING W/180° Ocean VIEWS

West Bay

8% off
S$4,842
for 7 nights, 1 apartment
S$692 per night
includes taxes & fees
LUXURY/OVERSIZED - 1 Bed/1.5 Bath near AMAZING SHORE DIVING W/180° Ocean VIEWS
CEMETERY BEACH near us. Pristine, Quiet, One of the Safest Beach Spots.
SEVEN MILE BEACH. Lots of eateries and bars along the length.
Property grounds
Comfortable queen bedroom with vanity area — practical for couples, solo travellers, or getting ready with ease.
Exceptional
(18 reviews)

S1 BP | Steps to Beach | Save 15% if Book Non-Refundable

West Bay

11% off
S$2,516
for 7 nights, 1 apartment
S$359 per night
includes taxes & fees
S1 BP | Steps to Beach | Save 15% if Book Non-Refundable
Pool
Exterior
Room
Interior
Exceptional
(24 reviews)

SAVE 20% at Coco Sands - 2 bed, beachfront, sea view condo

North Side

5% off
S$3,294
for 7 nights, 1 apartment
S$471 per night
includes taxes & fees
SAVE 20% at Coco Sands - 2 bed, beachfront, sea view condo

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting relaxing North Side

The island views and parks provide a pleasant backdrop to your holiday home in North Side. This relaxing city is known for its snorkelling, kayaking and coral reefs. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around North Side

Do you want to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that makes North Side a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • North Sound Golf Course (10.2 mi / 16.4 km)
  • Britannia Golf Course (11.2 mi / 18 km)

Exploring the natural landscape of North Side

Travellers enjoy North Side for its island views and seaside. Whether you're looking for adventure or just want to take in the scenery, North Side is a great place to get outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Grand Cayman Beaches (1.8 mi / 3 km)
  • Star Fish Point (4.4 mi / 7 km)
  • Rum Point Beach (4.4 mi / 7.1 km)
  • Starfish Beach (4.9 mi / 7.9 km)
  • Grand Cayman Blow Holes (6.6 mi / 10.6 km)
  • Spotts Beach (8.7 mi / 14.1 km)

How to get to and around North Side

The nearest airport is in George Town (GCM-Owen Roberts Intl.), located 10.4 mi (16.8 km) from the city centre.

Frequently asked questions

What is the best area to stay in North Side when booking a holiday rental?
Among the most desired neighbourhoods to get a holiday property in North Side is Breakers. Find your dream stay with Vrbo and explore this area as a local.
What is the most popular type of holiday rental accommodation in North Side?
Based on our research, condos are the most in-demand holiday property type in North Side. But as you'd expect, everyone's idea of an epic stay isn't the same. Vrbo has holiday rentals of all sizes and shapes, so you're sure to find your perfect match.
How much does it cost to rent a holiday rental in North Side?
A range of factors influence the price of a holiday rental in North Side, such as the season, length of stay and type of property. But, all Vrbo homes have something in common — incredible value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in North Side?
The average price for a holiday home near the beach in North Side depends on when you're travelling and the size and style of property you want. You can quickly and easily find prices on Vrbo by entering your preferred travel dates. Then use the filter tool to pick the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in North Side?
With 191 holiday rentals that allow pets, your little buddy can join in the fun on your North Side holiday. Use the filter tool to browse our pet-friendly holiday rentals and find your pawfect pad on Vrbo.
Can I rent a house with a pool in North Side?
Dig out your swimsuit and goggles, because there are 146 houses with a private pool in North Side. Settle in at one of these sought-after holiday homes and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in North Side?
A swimming pool, tennis and a chef head the list of most popular rental amenities in North Side. Whether you plan to go on your own, with a partner or as a family group, Vrbo will help you find a holiday rental that suits your style with all the features you'll enjoy.
Are there large group holiday rentals in North Side?
With 39 properties that can host 10 people or more in North Side, you won't have to leave anyone off your guest list. From family holidays to events like birthday and Christmas parties, Vrbo will help you find a large group rental to match the occasion.
Are there holiday rentals in North Side that welcome kids?
Bring the entire family together for an unforgettable adventure in North Side at one of our 191 family-friendly properties. A lot of these stays come with conveniences that are suitable for getaways with children, like laundry facilities, living rooms and entertainment areas. Simply check the "Properties good for families" filter box and select your favourite.
What are the top attractions for families in North Side?
Keeping the kids entertained during your North Side holiday is child's play with these fabulous family-friendly attractions:
  • Grand Cayman Beaches
  • Starfish Beach
  • Rum Point Beach
Are there one-bedroom holiday rentals in North Side?
Yes, you can take your pick from 17 one-bedroom rentals in North Side. Whether you'd like a secluded cottage or a cabin, our one-bedroom properties are great if you don't require loads of space. One of the best parts about having your own place? You won't need to share your trip with strangers.
Can I find two-bedroom holiday rentals in North Side?
North Side has 84 two-bedroom properties for you to select from. Find a holiday home with all the comfort and privacy you're looking for at an attractive price on Vrbo.
Are there holiday rentals with WiFi in North Side?
North Side has 100 holiday rentals with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to catching up on social media, these Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in North Side?
Work out your travel dates and then use the filters to find holiday rentals with ac in North Side on Vrbo. With 189 air-conditioned properties to choose from here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a holiday rental in North Side?
The minimum age allowed can differ across properties on Vrbo, so double-check the rules of the holiday rental in North Side you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in North Side for?
The amount of time you can rent a North Side holiday home for varies depending on the property. Just put in your preferred travel dates to browse available options offering longer term stays. They have all you require to make your extended getaway more comfortable and convenient, like kitchens and backyards. Some Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can stay even longer for less.