Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
The price is AU$273 per night from 10 Apr to 11 Apr
AU$273
includes taxes & fees
10 Apr - 11 Apr
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!
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
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

Rum Point
With a stay at this vacation home in North Side, you'll be on the waterfront, just a 1-minute walk from North Sound and 10 minutes by foot from Cayman Kai Public ...
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
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Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Stake Bay
When you a stay at this vacation home in West End, you'll be on the beach, just steps from Cayman Brac Beaches and Bamboo Bay.
Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool
Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen

Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen

South Sound
With a stay at this vacation home in George Town (South Sound), you'll be within a 15-minute drive of Port of Georgetown and Seven Mile Beach.
Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen
Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock

Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock

East End
With a stay at this vacation home in East End, you'll be on the beach, just steps from Grand Cayman Beaches and a 2-minute drive from Colliers Public Beach.
Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock
Ocean Paradise

Ocean Paradise

4 out of 5
1234 Rum Point Road, North Side, Grand Cayman
Located in North Side, Ocean Paradise is by the ocean, a 1-minute drive from North Sound and 8 minutes from Starfish Beach.
Ocean Paradise
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!!
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
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.
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
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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
272 Holiday Homes
Lowest Price
AU$273
Highest Price
AU$2,116
Popular accommodation
Slice of Paradise- 2 mins from Spotts Beach!, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!, Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool , Villa Mora: Luxe Beachfront Villa w/ Backyard Snorkeling, Pool, Spa + Outdoor Kitchen, Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock, Ocean Paradise, Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

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$937 per night from 22 Apr to 23 Apr
AU$937
includes taxes & fees
22 Apr - 23 Apr
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
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 AU$1,014 per night from 20 Apr to 21 Apr
AU$1,014
includes taxes & fees
20 Apr - 21 Apr
When you stay at Hotel Indigo Grand Cayman by IHG in Seven Mile Beach, you'll be on the beach, within a 15-minute drive of Seven Mile Beach and Port of ...
Hotel 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
The price is AU$2,116 per night from 25 Apr to 26 Apr
AU$2,116
includes taxes & fees
25 Apr - 26 Apr
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
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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 AU$572 per night from 12 Apr to 13 Apr
AU$572
includes taxes & fees
12 Apr - 13 Apr
When you stay at Hampton by Hilton Grand Cayman Seven Mile Beach in Seven Mile Beach, you'll be by the ocean, within a 5-minute drive of Camana Bay and Governor's ...
Hampton by Hilton Grand Cayman Seven Mile Beach
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.