Book Holiday Homes in Cayman Islands

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 Cayman Islands

Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
The price is NZ$299 per night from 1 Apr to 2 Apr
NZ$299
includes taxes & fees
1 Apr - 2 Apr
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!
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
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

Rum Point
Stay at this vacation home in North Side. Enjoy free WiFi, private pools, and a garden. Popular attractions Rum Point Beach and Cayman Kai Public Beach are located ...
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
Save an average of 15% on thousands of hotels when you're signed in
Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Stake Bay
Book a stay at this beach vacation home in West End. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Cayman Brac Beaches and Cayman Brac ...
Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool
Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen

Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen

South Sound
Book a stay at this beach vacation home in George Town. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Port of Georgetown and Seven ...
Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen
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
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
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
Book a stay at this beach vacation home in North Side. Enjoy a beach locale, balconies, and an in-room coffeemaker. Popular attractions Mastic Trail North Trailhead ...
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
Book a stay at this beach vacation home in North Side. Enjoy private pools, a beach locale, and a garden. Popular attractions Mastic Trail North Trailhead and ...
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Don't see what you're looking for?
See all available properties in Cayman Islands
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.

Cayman Islands 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 Cayman Islands vacation homes are the perfect way for you to wing it.

Holiday houses in Cayman Islands 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 Cayman Islands 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 Cayman Islands adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cayman Islands 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 Cayman Islands 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.

Cayman Islands Holiday Homes essential information

Accommodation
273 Holiday Homes
Lowest Price
NZ$299
Highest Price
NZ$2,327
Popular accommodation
Slice of Paradise- 2 mins from Spotts Beach!, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!, Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool , Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen, Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock, Ocean Paradise, Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Top trending hotels in Cayman Islands

Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
The price is NZ$995 per night from 30 Apr to 1 May
NZ$995
includes taxes & fees
30 Apr - 1 May
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and ...
Grand Cayman Marriott Resort
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
32 Seafire Way, Seven Mile Beach, West Bay
The price is NZ$1,041 per night from 30 Apr to 1 May
NZ$1,041
includes taxes & fees
30 Apr - 1 May
Stay at this 4.5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port ...
Hotel Indigo Grand Cayman by IHG
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
The price is NZ$2,327 per night from 25 Apr to 26 Apr
NZ$2,327
includes taxes & fees
25 Apr - 26 Apr
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
The Ritz-Carlton, Grand Cayman
Save an average of 15% on thousands of hotels when you're signed in
Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
22 Piper Way, Seven Mile Beach
The price is NZ$629 per night from 11 Apr to 12 Apr
NZ$629
includes taxes & fees
11 Apr - 12 Apr
Stay at this 4-star resort in Seven Mile Beach. Enjoy free breakfast, free parking, and a health club. Our guests praise the breakfast and the pool in our reviews. ...
Hampton by Hilton Grand Cayman Seven Mile Beach
Don't see what you're looking for?
See all available properties in Cayman Islands
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.