Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

THE YELLOW HOUSE -  WE ARE BACK FROM HIATUS -  STEPS TO THE BEACH!

THE YELLOW HOUSE - WE ARE BACK FROM HIATUS - STEPS TO THE BEACH!

East End
When you stay at this vacation home in East End, you'll be by the sea, within a 5-minute drive of Grand Cayman Beaches and Grand Cayman Blow Holes.
THE YELLOW HOUSE - WE ARE BACK FROM HIATUS - STEPS TO THE 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
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!!
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
When you a stay at this vacation home in North Side, you'll be on the beach, within a 5-minute walk of North Sound and Grand Cayman Beaches.
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
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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!
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 10-minute walk of Grand Cayman Beaches and North Sound.
Coco 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
With a stay at this vacation home in George Town, you'll be within a 10-minute drive of Port of Georgetown and North Sound.
Slice of Paradise- 2 mins from Spotts Beach!
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 North Sound and Cayman Kai Public Beach.
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
Private 4 bd/3bth home on Boggy Sands Rd, Fantastic Location, Heated Pool

Private 4 bd/3bth home on Boggy Sands Rd, Fantastic Location, Heated Pool

West Bay
With a stay at this vacation home in West Bay, you'll be by the sea, within a 15-minute drive of Port of Georgetown and Kittiwake Shipwreck and Artificial ...
Private 4 bd/3bth home on Boggy Sands Rd, Fantastic Location, Heated Pool
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
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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
230 Holiday Homes
Lowest Price
AU$1,046
Highest Price
AU$5,510
Popular accommodation
THE YELLOW HOUSE - WE ARE BACK FROM HIATUS - STEPS TO THE BEACH!, Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, Coco Kai Beach Front Villa with Heated Pool and Private Dock, Slice of Paradise- 2 mins from Spotts Beach!, So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling, Private 4 bd/3bth home on Boggy Sands Rd, Fantastic Location, Heated Pool , Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Top trending hotels in Cayman Islands

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
The price is AU$1,046 per night from 5 Jan to 6 Jan
AU$1,046
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Seven Mile Beach, Grand Cayman Marriott Resort is on the waterfront, a 4-minute walk from Seven Mile Beach and 12 minutes by foot from Camana ...
Grand Cayman Marriott Resort
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Seven Mile Beach, P.O. Box 30620, Seven Mile Beach, Grand Cayman
The price is AU$1,447 per night from 12 Jan to 13 Jan
AU$1,447
includes taxes & fees
12 Jan - 13 Jan 2025
When you stay at The Westin Grand Cayman Seven Mile Beach Resort & Spa in Seven Mile Beach, you'll be on the waterfront, within a 5-minute drive of The Strand ...
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
The price is AU$1,534 per night from 5 Jan to 6 Jan
AU$1,534
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Kimpton Seafire Resort + Spa, an IHG Hotel in Seven Mile Beach, you'll be on the beach, within a 15-minute drive of Port of Georgetown and Tiki ...
Kimpton Seafire Resort + Spa, an IHG Hotel
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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 AU$5,510 per night from 3 Jan to 4 Jan
AU$5,510
includes taxes & fees
3 Jan - 4 Jan 2025
With a stay at The Ritz-Carlton, Grand Cayman in Seven Mile Beach, you'll be on the beach, within a 10-minute drive of Port of Georgetown and Seven Mile ...
The 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.

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^Subject to availability and chosen travel dates.