Book Holiday Homes in Cayman Islands

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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
Stay at this beach holiday home in North Side. Enjoy private pools, a beach locale and a garden. Popular attractions Grand Cayman Beaches and Cayman Kai Public ...
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
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Grand Cayman Beaches and Mastic Trail ...
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 NZ$288 per night from 4 May to 5 May
NZ$288
4 May - 5 May
includes taxes & fees
Stay at this holiday home in George Town. Enjoy free Wi-Fi, a garden and patios. Popular attractions Port of Georgetown and Seven Mile Beach are located ...
Opens in a new windowSlice of Paradise- 2 mins from Spotts Beach!
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Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

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

Grand Cayman Grand Cayman
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Grand Cayman Beaches and Star Fish Point are ...
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
Stay at this beach holiday home in North Side. Enjoy a beach locale, laundry facilities and patios. Popular attractions Grand Cayman Beaches and Mastic Trail ...
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
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Grand Cayman Beaches and Cayman Kai ...
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 NZ$1,345 per night from 17 May to 18 May
NZ$1,345
17 May - 18 May
includes taxes & fees
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Grand Cayman Beaches and Cayman Kai Public 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
Stay at this beach holiday home in North Side. Enjoy private pools, a beach locale and breakfast (surcharge). Popular attractions Grand Cayman Beaches and Mastic ...
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
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Grand Cayman Beaches and Cayman Kai Public ...
Opens in a new windowRum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
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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
278 Holiday Homes
Lowest Price
NZ$288
Highest Price
NZ$2,371
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 NZ$818 per night from 5 May to 6 May
NZ$818
5 May - 6 May
includes taxes & fees
Stay at this luxury hotel in Seven Mile Beach. Enjoy free Wi-Fi, free valet parking and 4 restaurants. Popular attractions Seven Mile Beach and Port of Georgetown ...
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 NZ$542 per night from 31 May to 1 June
NZ$542
31 May - 1 June
includes taxes & fees
Stay at this resort in Seven Mile Beach. Enjoy free breakfast, free parking and a beach locale. Our guests praise the breakfast and the pool in their reviews. ...
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 NZ$882 per night from 14 May to 15 May
NZ$882
14 May - 15 May
includes taxes & fees
Stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowGrand Cayman Marriott Resort
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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 NZ$2,371 per night from 8 May to 9 May
NZ$2,371
8 May - 9 May
includes taxes & fees
Stay at this luxury resort in Seven Mile Beach. Enjoy free Wi-Fi, free valet parking and 2 outdoor pools. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Ritz-Carlton, Grand Cayman
Don't see what you're looking for?
See all available properties in Cayman Islands
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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.