Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

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 Cayman Islands
Stay at this beach holiday home in North Side. Enjoy a beach locale, laundry facilities and patios. Popular attractions Mastic Trail North Trailhead and Cayman ...
Opens in a new windowAzure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, 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 North Side
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Cayman Kai Public Beach and Rum Point ...
Opens in a new windowSo Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Rum Point Grand Cayman
Stay at this holiday home in North Side. Enjoy laundry facilities, patios and air conditioning. Popular attractions Star Fish Point and Starfish Beach are located ...
Opens in a new windowEscape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club
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Ocean Paradise

Ocean Paradise

4 out of 5
1234 Rum Point Road North Side Grand Cayman
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Cayman Kai Public Beach and Star Fish Point are ...
Opens in a new windowOcean Paradise
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

North Side
Stay at this beach holiday home in North Side. Enjoy private pools, a beach locale and breakfast (surcharge). Popular attractions Mastic Trail North Trailhead ...
Opens in a new windowCORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
Stay at this beach holiday home in North Side. Enjoy private pools, a beach locale and a garden. Popular attractions Mastic Trail North Trailhead and Grand Cayman ...
Opens in a new windowBEACHFRONT w/ Private Dock-50 ft Pool-Theatre
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 Grand Cayman
Stay at this beach holiday home in North Side. Enjoy private pools, a beach locale and a garden. Popular attractions Grand Cayman Beaches and Cayman Kai Public ...
Opens in a new windowThe Pink Beach House - Private House and Pool directly on the Beach, Rum Point
50% off 4th night! Private, quiet oceanfront home, wrap-around screened porch.

50% off 4th night! Private, quiet oceanfront home, wrap-around screened porch.

North Side Grand Cayman
Stay at this beach holiday home in North Side. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Babylon (Dive Site) and Cayman Crystal Caves ...
Opens in a new window50% off 4th night! Private, quiet oceanfront home, wrap-around screened porch.
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island George Town
The price is NZ$293 per night from 1 Jan to 2 Jan
NZ$293
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this holiday home in George Town. Enjoy free Wi-Fi, a garden and patios. Popular attractions Port of Georgetown and Seven Mile Beach are located ...
Opens in a new windowSlice of Paradise- 2 mins from Spotts Beach!
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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
264 Holiday Homes
Lowest Price
NZ$293
Highest Price
NZ$908
Popular accommodation
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling, Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club, Ocean Paradise, CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, 50% off 4th night! Private, quiet oceanfront home, wrap-around screened porch., Slice of Paradise- 2 mins from Spotts Beach!

Top trending hotels in Cayman Islands

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
The price is NZ$610 per night from 16 Dec to 17 Dec
NZ$610
16 Dec - 17 Dec
includes taxes & fees
Stay at this resort in Seven Mile Beach. Enjoy free breakfast, free parking and a beach locale. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowHampton by Hilton Grand Cayman Seven Mile Beach
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
The price is NZ$810 per night from 15 Dec to 16 Dec
NZ$810
15 Dec - 16 Dec
includes taxes & fees
Stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowGrand Cayman Marriott Resort
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
The price is NZ$908 per night from 17 Dec to 18 Dec
NZ$908
17 Dec - 18 Dec
includes taxes & fees
Stay at this luxury hotel in Seven Mile Beach. Enjoy free Wi-Fi, free valet parking and 4 restaurants. Popular attractions Seven Mile Beach and Port of Georgetown ...
Opens in a new windowHotel 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
The price is NZ$446 per night from 15 Dec to 16 Dec
NZ$446
15 Dec - 16 Dec
includes taxes & fees
Stay at this business-friendly hotel in Seven Mile Beach. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
Opens in a new windowThe Locale Hotel 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.