Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

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 ...
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
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
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 ...
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
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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 ...
The peace and tranquility of this cottage Works Wonders on the soul....
Luxurious 2 Bdr Beachfront Villa - Coral Beach House - Excellent Cayman value!

Luxurious 2 Bdr Beachfront Villa - Coral Beach House - Excellent Cayman value!

Bodden Town
Book a stay at this beach vacation home in Bodden Town. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Mission House and Boddentown ...
Luxurious 2 Bdr Beachfront Villa - Coral Beach House - Excellent Cayman value!
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 ...
Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach)
Coco Kai Beach Front Villa with Heated Pool and Private Dock

Coco Kai Beach Front Villa with Heated Pool and Private Dock

North Side
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Mastic Trail North Trailhead and ...
Coco Kai Beach Front Villa with Heated Pool and Private Dock
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

Grand Cayman
Book a stay at this beach vacation home in North Side. Enjoy private pools, a beach locale, and a garden. Our guests praise the helpful staff in our reviews. ...
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of 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
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Cayman Kai Public Beach and ...
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
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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
263 Holiday Homes
Lowest Price
NZ$490
Highest Price
NZ$1,397
Popular accommodation
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, The peace and tranquility of this cottage Works Wonders on the soul...., Luxurious 2 Bdr Beachfront Villa - Coral Beach House - Excellent Cayman value!, Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach), Coco Kai Beach Front Villa with Heated Pool and Private Dock, SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point , So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

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
Fully refundable
The price is NZ$699 per night from 14 Aug to 15 Aug
NZ$699
14 Aug - 15 Aug
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 ...
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$1,397 per night from 24 Aug to 25 Aug
NZ$1,397
24 Aug - 25 Aug
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 ...
The Ritz-Carlton, Grand Cayman
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$490 per night from 7 Aug to 8 Aug
NZ$490
7 Aug - 8 Aug
includes taxes & fees
Stay at this 4-star resort in Seven Mile Beach. Enjoy free breakfast, free parking, and a beach locale. Our guests praise the breakfast and the pool in our reviews. ...
Hampton by Hilton Grand Cayman Seven Mile Beach
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Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
The price is NZ$1,088 per night from 30 Aug to 31 Aug
NZ$1,088
30 Aug - 31 Aug
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 ...
Kimpton Seafire Resort + Spa by IHG
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.

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^Subject to availability and chosen travel dates.