Book Holiday Homes in Grand Cayman

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Featured Holiday Homes in Grand Cayman

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!
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.
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

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

Rum Point
Located in North Side, this vacation home is by the sea, within a 15-minute walk of Cayman Kai Public Beach and Star Fish Point.
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
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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.
Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach)
LEMONGRASS HAVEN 
3 bedroom home

LEMONGRASS HAVEN 3 bedroom home

Georgetown
With a stay at this vacation home in West Bay, you'll be within a 10-minute drive of Seven Mile Beach and North Sound.
LEMONGRASS HAVEN 3 bedroom home
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 ...
The peace and tranquility of this cottage Works Wonders on the soul....
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!!
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

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

North Side
When you stay at this vacation home in North Side, you'll be on the beach, within a 15-minute walk of Grand Cayman Beaches and North Sound.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
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
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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.

Grand Cayman 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 Grand Cayman vacation homes are the perfect way for you to wing it.

Holiday houses in Grand Cayman 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 Grand Cayman 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 Grand Cayman adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Grand Cayman 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 Grand Cayman 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.

Grand Cayman Holiday Homes essential information

Accommodation
249 Holiday Homes
Lowest Price
AU$630
Highest Price
AU$1,241
Popular accommodation
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!, Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach), LEMONGRASS HAVEN 3 bedroom home, The peace and tranquility of this cottage Works Wonders on the soul...., Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!, CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana, Ocean Paradise

Top trending hotels in Grand Cayman

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$934 per night from 13 Sept to 14 Sept
AU$934
13 Sept - 14 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 ...
Kimpton 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$630 per night from 28 Aug to 29 Aug
AU$630
28 Aug - 29 Aug
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 ...
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
Fully refundableReserve now, pay when you stay
The price is AU$1,241 per night from 23 Aug to 24 Aug
AU$1,241
23 Aug - 24 Aug
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 ...
The 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$670 per night from 7 Sept to 8 Sept
AU$670
7 Sept - 8 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 ...
Grand 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.