Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

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.
Opens in a new windowThe Pink Beach House - Private House and Pool directly on the Beach, Rum Point
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 ...
Opens in a new windowThe peace and tranquility of this cottage Works Wonders on the soul....
Relax at Coconut Bay!

Relax at Coconut Bay!

West Bay
With a stay at this vacation home in West Bay (Northwest Point), you'll be within a 10-minute drive of Seven Mile Beach and Boatswain's Beach.
Opens in a new windowRelax at Coconut Bay!
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BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
Located in North Side, this vacation home is by the ocean, within a 15-minute walk of Grand Cayman Beaches and North Sound.
Opens in a new windowBEACHFRONT w/ Private Dock-50 ft Pool-Theatre
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 ...
Opens in a new windowReef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
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.
Opens in a new windowCaribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

North Side, North Side
When you a stay at this villa in North Side, you'll be on the beach, just steps from North Sound and Grand Cayman Beaches.
Opens in a new windowRum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
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, you'll be centrally located in Bodden Town, within a 15-minute drive of Port of Georgetown and Spotts Beach.
Opens in a new windowSavhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts 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.
Opens in a new windowAzure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum 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
278 Holiday Homes
Lowest Price
AU$613
Highest Price
AU$1,222
Popular accommodation
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, The peace and tranquility of this cottage Works Wonders on the soul...., Relax at Coconut Bay!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point, Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes., Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach), Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Top trending hotels in Cayman Islands

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Fully refundable
The price is AU$902 per night from 19 Sept to 20 Sept
AU$902
19 Sept - 20 Sept
includes taxes & fees
When you stay at Kimpton Seafire Resort + Spa by IHG in Seven Mile Beach, you'll be on the beach, within a 5-minute walk of Seven Mile Beach and Grand Cayman ...
Opens in a new windowKimpton Seafire Resort + Spa by IHG
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
The price is AU$613 per night from 28 Sept to 29 Sept
AU$613
28 Sept - 29 Sept
includes taxes & fees
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 ...
Opens in a new windowHotel Indigo Grand Cayman by IHG
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
Fully refundableReserve now, pay when you stay
The price is AU$1,222 per night from 3 Oct to 4 Oct
AU$1,222
3 Oct - 4 Oct
includes taxes & fees
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 ...
Opens in a new windowThe Ritz-Carlton, Grand Cayman
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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
Fully refundableReserve now, pay when you stay
The price is AU$671 per night from 21 Sept to 22 Sept
AU$671
21 Sept - 22 Sept
includes taxes & fees
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 ...
Opens in a new windowGrand Cayman Marriott Resort
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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.