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
Stay at this vacation home in East End. Enjoy free WiFi, private pools, and patios. Popular attractions Queen Elizabeth II Botanic Park and Mastic Trail South ...
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
Book a stay at this beach vacation home in North Side. Enjoy a beach locale and air conditioning. Popular attractions Mastic Trail North Trailhead and Babylon ...
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
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 ...
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
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!
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
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
The price is NZ$301 per night from 6 Jan to 7 Jan
NZ$301
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this vacation home in George Town. Enjoy free WiFi, a garden, and patios. Popular attractions Port of Georgetown and Spotts Beach are located ...
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
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
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
Book a stay at this family-friendly vacation home in West Bay. Enjoy free WiFi, private pools, and a water park. Popular attractions Port of Georgetown and Cemetery ...
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
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
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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
232 Holiday Homes
Lowest Price
NZ$301
Highest Price
NZ$6,100
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 NZ$1,344 per night from 5 Jan to 6 Jan
NZ$1,344
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and ...
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 NZ$1,668 per night from 5 Jan to 6 Jan
NZ$1,668
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 6 restaurants, and a private beach. Our guests praise the helpful staff and ...
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 NZ$1,698 per night from 5 Jan to 6 Jan
NZ$1,698
includes taxes & fees
5 Jan - 6 Jan 2025
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, 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 NZ$6,100 per night from 5 Jan to 6 Jan
NZ$6,100
includes taxes & fees
5 Jan - 6 Jan 2025
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
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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.