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

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 Grand Cayman
When you stay at this vacation home in North Side, you'll be on the beach, within a 5-minute walk of Grand Cayman Beaches and North Sound.
Opens in a new windowThe Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Coco Kai Beach Front Villa with Heated Pool and Private Dock

Coco Kai Beach Front Villa with Heated Pool and Private Dock

North Side 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
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island George Town
The price is AU$242 per night from 31 May to 1 June
AU$242
31 May - 1 June
includes taxes & fees
With a stay at this vacation home in George Town, you'll be a 3-minute drive from Grand Cayman Beaches and 9 minutes from Port of Georgetown.
Opens in a new windowSlice of Paradise- 2 mins from Spotts Beach!
Save an average of 15% on thousands of hotels when you're signed in
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Grand Cayman Grand Cayman
With a 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 windowCaribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish 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!!

Grand Cayman Cayman Islands
With a 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!!
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 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 Cayman Kai Public Beach.
Opens in a new windowSo Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
Ocean Paradise

Ocean Paradise

4 out of 5
1234 Rum Point Road North Side Grand Cayman
The price is AU$1,066 per night from 17 May to 18 May
AU$1,066
17 May - 18 May
includes taxes & fees
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
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

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 windowCORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
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 stay at this vacation home in North Side, you'll be on the beach, just steps from Grand Cayman Beaches and North Sound.
Opens in a new windowRum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
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
175 Holiday Homes
Lowest Price
AU$242
Highest Price
AU$1,945
Popular accommodation
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Coco Kai Beach Front Villa with Heated Pool and Private Dock, Slice of Paradise- 2 mins from Spotts Beach!, Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point, Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling, Ocean Paradise, CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana, Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Top trending hotels in Cayman Islands

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 AU$649 per night from 5 May to 6 May
AU$649
5 May - 6 May
includes taxes & fees
When you stay at Hotel Indigo Grand Cayman by IHG in Seven Mile Beach, you'll be near the beach, within a 5-minute walk of Seven Mile Beach and Grand Cayman ...
Opens in a new windowHotel Indigo Grand Cayman by IHG
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
Fully refundableReserve now, pay when you stay
The price is AU$444 per night from 31 May to 1 June
AU$444
31 May - 1 June
includes taxes & fees
When you stay at Hampton by Hilton Grand Cayman Seven Mile Beach in Seven Mile Beach, you'll be on the beach, within a 5-minute drive of Camana Bay and Port ...
Opens in a new windowHampton by Hilton Grand Cayman Seven Mile Beach
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
The price is AU$749 per night from 31 May to 1 June
AU$749
31 May - 1 June
includes taxes & fees
Located in Seven Mile Beach, Grand Cayman Marriott Resort is on the waterfront, a 4-minute walk from Seven Mile Beach and 12 minutes by foot from Camana ...
Opens in a new windowGrand Cayman Marriott Resort
Save an average of 15% on thousands of hotels when you're signed in
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road Seven Mile Beach Grand Cayman
The price is AU$1,945 per night from 10 May to 11 May
AU$1,945
10 May - 11 May
includes taxes & fees
With a stay at The Ritz-Carlton, Grand Cayman in Seven Mile Beach, you'll be on the beach, a 2-minute walk from Seven Mile Beach and a 3-minute drive from Grand ...
Opens in a new windowThe Ritz-Carlton, Grand Cayman
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.