Book Holiday Homes in Grand Cayman

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Grand Cayman

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
Located in East End, this vacation home is by the ocean, within a 5-minute drive of Mastic Trail South Trailhead and Grand Cayman Blow Holes.
Opens in a new windowThe peace and tranquility of this cottage Works Wonders on the soul....
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
Located in North Side, this villa is by the ocean, a 1-minute drive from North Sound and 5 minutes from Cayman Kai Public Beach.
Opens in a new windowRum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
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 steps from North Sound and a 3-minute drive from Cayman Kai Public Beach.
Opens in a new windowReef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Save an average of 15% on thousands of hotels when you're signed in
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 5-minute drive of North Sound and Mastic Trail North Trailhead.
Opens in a new windowBEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Coco Kai Beach Front Villa with Heated Pool and Private Dock

Coco Kai Beach Front Villa with Heated Pool and Private Dock

North Side
When you stay at this vacation home in North Side, you'll be on the beach, within a 5-minute drive of North Sound and Mastic Trail North Trailhead.
Opens in a new windowCoco Kai Beach Front Villa with Heated Pool and Private Dock
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
With a stay at this vacation home in North Side, you'll be on the beach, just steps from North Sound and a 5-minute drive from Cayman Kai Public Beach.
Opens in a new windowThe Pink Beach House - Private House and Pool directly on the Beach, Rum Point
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 Cayman Motor Museum.
Opens in a new windowRelax at Coconut Bay!
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

Grand Cayman
With a stay at this vacation home in North Side, you'll be on the beach, just steps from North Sound and a 2-minute drive from Cayman Kai Public Beach.
Opens in a new windowSEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
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 North Sound and Mastic Trail North Trailhead.
Opens in a new windowAzure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
Don't see what you're looking for?
See all available properties in Grand Cayman
View all properties
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$699
Highest Price
AU$1,241
Popular accommodation
The peace and tranquility of this cottage Works Wonders on the soul...., Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes., Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, BEACHFRONT w/ Private Dock-50 ft Pool-Theatre, Coco Kai Beach Front Villa with Heated Pool and Private Dock, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Relax at Coconut Bay!, SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point , Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Top trending hotels in Grand Cayman

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$699 per night from 30 Sept to 1 Oct
AU$699
30 Sept - 1 Oct
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
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$1,026 per night from 17 Oct to 18 Oct
AU$1,026
17 Oct - 18 Oct
includes taxes & fees
With a stay at Kimpton Seafire Resort + Spa by IHG in Seven Mile Beach, you'll be on the beach, just a 3-minute walk from Seven Mile Beach and a 2-minute drive ...
Opens in a new windowKimpton Seafire Resort + Spa 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 4 Oct to 5 Oct
AU$1,241
4 Oct - 5 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
Save an average of 15% on thousands of hotels when you're signed in
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$709 per night from 30 Sept to 1 Oct
AU$709
30 Sept - 1 Oct
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
Don't see what you're looking for?
See all available properties in Grand Cayman
View all properties
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.