North Side holiday rentals

We found 1,315 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:11 Dec - 18 Dec

View looking back from the beach
View from the Master bedroom
View from the couch
Property grounds
Exceptional
(80 reviews)

BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH

North Side

8% off
S$3,512
for 7 nights, 1 villa
S$502 per night
includes taxes & fees
BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH
Great Snorkeling
View From Condo
Guest Bedroom
Screen Lanai
Exceptional
(94 reviews)

Paradise Found Oceanfront Condo - Flexible Cancellation

North Side

8% off
S$3,118
for 7 nights, 1 apartment
S$445 per night
includes taxes & fees
Paradise Found Oceanfront Condo - Flexible Cancellation
Living area
Exterior
Private kitchen
Pool
Exceptional
(51 reviews)

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

Seven Mile Beach

8% off
S$5,114
for 7 nights, 1 apartment
S$731 per night
includes taxes & fees
Seven Mile Beach -2nd Floor Beach View at Sunset Cove
Dining
Living area
Property grounds
Pool
Exceptional
(17 reviews)

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

Seven Mile Beach

8% off
S$7,435
for 7 nights, 1 apartment
S$1,062 per night
includes taxes & fees
Modern Condo - Seven Mile Beach - Cayman Islands - Walk Everywhere
The Pool
Beach
Dining
Terrace/patio
Exceptional
(5 reviews)

7 Mile Beach Condo with Pool View and Rooftop

West Bay

5% off
S$17,140
for 7 nights, 1 apartment
S$2,449 per night
includes taxes & fees
7 Mile Beach Condo with Pool View and Rooftop
CAR RENTALS available! Simply book in advance on your Guest Portal.
SEVEN MILE BEACH. Lots of eateries and bars along the length.
Living area
Cemetery Beach
Exceptional
(5 reviews)

S2 BP | Steps to Beach | Save 15% if Book Non-Refundable

West Bay

7% off
S$2,966
for 7 nights, 1 apartment
S$424 per night
includes taxes & fees
S2 BP | Steps to Beach | Save 15% if Book Non-Refundable
Living area
Exterior detail
Private kitchen
Room
Exceptional
(113 reviews)

Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove

George Town

8% off
S$1,888
for 7 nights, 1 apartment
S$270 per night
includes taxes & fees
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
Large kitchen with peninsula dining if not outdoors
Pool and beach are less than 30 steps away
What a view!
Ocean and pool (to the right) just a few steps from bedroom patio
Exceptional
(111 reviews)

Cayman White Sand Beach + Quiet Pool = Relaxation

West Bay

8% off
S$3,599
for 7 nights, 1 apartment
S$514 per night
includes taxes & fees
Cayman White Sand Beach + Quiet Pool = Relaxation
Pool in the Courtyard just steps away from the door
Outdoor dining
Living area
Great for Little Kids!
Exceptional
(46 reviews)

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

Seven Mile Beach

8% off
S$4,965
for 7 nights, 1 apartment
S$709 per night
includes taxes & fees
Beachfront Walkout Condo - Seven Mile Beach - Quiet/Away from Resort Crowds
Pool at The Retreat for guests
Starfish Point 2 miles away from condo
Master Bedroom King bed, nightstands with storage/ceiling fan/blackout curtains
Property The Retreat
Exceptional
(37 reviews)

2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach

North Side

8% off
S$3,661
for 7 nights, 1 apartment
S$523 per night
includes taxes & fees
2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach
Sunset Aerial View (104 is left ground corner unit)
SC 104 Deck Oceanview
Private kitchen
SC 104 Master BR
Exceptional
(68 reviews)

Cayman Famous Seven Mile Beach Sunset Cove corner unit-RIGHT ON BEACH STEPS AWAY

Seven Mile Beach

8% off
S$7,519
for 7 nights, 1 apartment
S$1,074 per night
includes taxes & fees
Cayman Famous Seven Mile Beach Sunset Cove corner unit-RIGHT ON BEACH STEPS AWAY
Dining
Outdoor dining
Living area
Living area
Wonderful
(18 reviews)

Remodelled Beach/Pool View Condo

Seven Mile Beach

8% off
S$5,807
for 7 nights, 1 apartment
S$830 per night
includes taxes & fees
Remodelled Beach/Pool View Condo
Living area
Pool
Room
Room
Exceptional
(105 reviews)

World Famous Seven Mile Beach "Location, Cayman Islands" Welcome to Paradise.

Seven Mile Beach

8% off
S$4,914
for 7 nights, 1 apartment
S$702 per night
includes taxes & fees
World Famous Seven Mile Beach "Location, Cayman Islands" Welcome to Paradise.
Interior
Living area
Pool
Living area
Exceptional
(68 reviews)

Escape to Paradise – Beautiful & Budget-Friendly Condo!

North Side

8% off
S$2,946
for 7 nights, 1 apartment
S$421 per night
includes taxes & fees
Escape to Paradise – Beautiful & Budget-Friendly Condo!
...or marvel at the beauty of native plants in the nearby botanical garden
...with an infinity pool...
Prepare your morning coffee overlooking tranquil waves
Beach hop to nearby Rum Point
Exceptional
(95 reviews)

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

East End

8% off
S$3,966
for 7 nights, 1 apartment
S$567 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$12,261
for 7 nights, 1 apartment
S$1,752 per night
includes taxes & fees
Luxury Designer Seven Mile Beachfront Condo Townhouse -Direct Walk-out to Beach!
Kitchen (2)
Full Kitchen
Pool, steps from the private fenced-in backyard.
Cayman Pickleball Courts
Exceptional
(7 reviews)

West Bay Oasis: 2BR Condo w/Pool

West Bay

8% off
S$4,986
for 7 nights, 1 apartment
S$712 per night
includes taxes & fees
West Bay Oasis: 2BR Condo w/Pool
Comfortable queen bedroom with vanity area — practical for couples, solo travellers, or getting ready with ease.
SEVEN MILE BEACH. Lots of eateries and bars along the length.
CEMETERY BEACH near us. Pristine, Quiet, One of the Safest Beach Spots.
Property grounds
Exceptional
(18 reviews)

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

West Bay

11% off
S$2,170
for 7 nights, 1 apartment
S$310 per night
includes taxes & fees
S1 BP | Steps to Beach | Save 15% if Book Non-Refundable
Full kitchen
Great views and sunsets from our private beach
1st floor view from kitchen
on site Diving Facilities
Exceptional
(64 reviews)

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

West Bay

8% off
S$5,135
for 7 nights, 1 apartment
S$734 per night
includes taxes & fees
Coconut Bay-Cayman Divers Delight...END UNIT with Extra Living Space/Windows
Dining
Interior
Pool
Room
Exceptional
(35 reviews)

Ocean/Beachfront - stunning views! Seabreeze Villas

Bodden Town

8% off
S$5,338
for 7 nights, 1 apartment
S$763 per night
includes taxes & fees
Ocean/Beachfront - stunning views! Seabreeze Villas
Balcony includes dining table, loungers, and drying racks.
Living area with floor to ceiling sliding doors.
Full kitchen with breakfast bar and separate indoor dining area
Yes!, That is a queen-size pull-out sofa bed in the living area.
Exceptional
(8 reviews)

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

West Bay

8% off
S$4,458
for 7 nights, 1 apartment
S$637 per night
includes taxes & fees
LUXURY/OVERSIZED - 1 Bed/1.5 Bath near AMAZING SHORE DIVING W/180° Ocean VIEWS

  • 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)
  • Starfish Point (4.4 mi / 7 km)
  • Rum Point Beach (4.4 mi / 7.1 km)
  • Grand Cayman Blow Holes (6.6 mi / 10.6 km)
  • Spotts Beach (8.7 mi / 14.1 km)
  • Governor's Beach (11.3 mi / 18.2 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.