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
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.
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
With a stay at this vacation home in East End, you'll be on the beach, just steps from Grand Cayman Beaches and a 3-minute drive from Mastic Trail South ...
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
When you 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.
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
When you a stay at this vacation home in North Side, you'll be on the beach, just steps from North Sound and Star Fish Point.
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
When you a stay at this vacation home in North Side, you'll be on the beach, just steps from Cayman Kai Public Beach and North Sound.
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
With a stay at this vacation home in Bodden Town, you'll be on the beach, just a 1-minute walk from Grand Cayman Beaches and 11 minutes by foot from Mission ...
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
With a stay at this vacation home in Bodden Town, you'll be within a 15-minute drive of Port of Georgetown and Spotts Beach.
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
With a stay at this vacation home in North Side, you'll be on the beach, just a 1-minute walk from North Sound and 15 minutes by foot from Grand Cayman ...
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
When you stay at this villa in North Side, you'll be on the beach, within a 15-minute walk of Grand Cayman Beaches and North Sound.
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
273 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
When you stay at The Ritz-Carlton, Grand Cayman in Seven Mile Beach, you'll be on the beach, a 1-minute drive from Seven Mile Beach and 8 minutes from Port of ...
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
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 ...
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
When you stay at Hotel Indigo Grand Cayman by IHG in Seven Mile Beach, you'll be near the beach, within a 15-minute drive of Seven Mile Beach and Port of ...
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
Located in Seven Mile Beach, The Locale Hotel Grand Cayman is on the beach, a 3-minute walk from Seven Mile Beach and 9 minutes by foot from Camana Bay.
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.