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
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 ...
Opens in a new windowThe Pink Beach House - Private House and Pool directly on the Beach, Rum Point
The peace and tranquility of this cottage Works Wonders on the soul....

The peace and tranquility of this cottage Works Wonders on the soul....

Grand Cayman
Book a stay at this beach vacation home in East End. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Queen Elizabeth II Botanic Park ...
Opens in a new windowThe peace and tranquility of this cottage Works Wonders on the soul....
Relax at Coconut Bay!

Relax at Coconut Bay!

West Bay
Book a stay at this beach vacation home in West Bay. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Seven Mile Beach and Boatswain's ...
Opens in a new windowRelax at Coconut Bay!
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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 ...
Opens in a new windowBEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Cayman Islands
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Cayman Kai Public Beach and Star ...
Opens in a new windowReef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

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

Grand Cayman
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Star Fish Point and Starfish Beach ...
Opens in a new windowCaribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
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
Book a stay at this beach villa in North Side. Enjoy private pools, a beach locale, and laundry facilities. Popular attractions Grand Cayman Beaches and Cayman ...
Opens in a new windowRum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach)

Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach)

Savannah
Book a stay at this family-friendly vacation home in Bodden Town. Enjoy free WiFi, private pools, and a water park. Popular attractions Port of Georgetown and ...
Opens in a new windowSavhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach)
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, laundry facilities, and patios. Popular attractions Mastic Trail North Trailhead ...
Opens in a new windowAzure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
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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
275 Holiday Homes
Lowest Price
NZ$684
Highest Price
NZ$1,364
Popular accommodation
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, The peace and tranquility of this cottage Works Wonders on the soul...., Relax at Coconut Bay!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point, Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes., Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach), Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Top trending hotels in Cayman Islands

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Fully refundable
The price is NZ$1,008 per night from 19 Sept to 20 Sept
NZ$1,008
19 Sept - 20 Sept
includes taxes & fees
Stay at this 5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
Opens in a new windowKimpton Seafire Resort + Spa by IHG
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
Fully refundable
The price is NZ$684 per night from 28 Sept to 29 Sept
NZ$684
28 Sept - 29 Sept
includes taxes & fees
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 ...
Opens in a new windowHotel 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
Fully refundableReserve now, pay when you stay
The price is NZ$1,364 per night from 3 Oct to 4 Oct
NZ$1,364
3 Oct - 4 Oct
includes taxes & fees
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 ...
Opens in a new windowThe Ritz-Carlton, Grand Cayman
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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
Fully refundableReserve now, pay when you stay
The price is NZ$750 per night from 21 Sept to 22 Sept
NZ$750
21 Sept - 22 Sept
includes taxes & fees
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the ...
Opens in a new windowGrand Cayman Marriott Resort
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.