Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

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
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....
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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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 ...
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish 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
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)
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!
Far Tortuga: Single Level Spacious Beach Villa w/ Heated Pool and Private Dock

Far Tortuga: Single Level Spacious Beach Villa w/ Heated Pool and Private Dock

2 out of 5
North Side
Book a stay at this beach villa in North Side. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Mastic Trail North Trailhead and Grand ...
Far Tortuga: Single Level Spacious Beach Villa w/ Heated Pool and Private Dock
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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
Highest Price
Popular accommodation
Coco Kai Beach Front Villa with Heated Pool and Private Dock, The peace and tranquility of this cottage Works Wonders on the soul...., Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point, So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling, 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), Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, Far Tortuga: Single Level Spacious Beach Villa w/ Heated Pool and Private Dock

Top trending hotels in Cayman Islands

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
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
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
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
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
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The Locale Hotel Grand Cayman

The Locale Hotel Grand Cayman

3.5 out of 5
455 West Bay Road, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star beach hotel in Seven Mile Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Locale Hotel Grand Cayman
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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.