Book Holiday Homes in Grand Cayman

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Featured Holiday Homes in Grand Cayman

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
With a 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!!
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
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 Cayman Kai Public Beach.
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
With a stay at this vacation home in North Side, you'll be within a 10-minute drive of Grand Cayman Beaches and North Sound.
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
Located in North Side, Ocean Paradise is by the ocean, a 1-minute drive from North Sound and 8 minutes from Starfish Beach.
Opens in a new windowOcean Paradise
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.
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
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.
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
When you stay at this vacation home in North Side, you'll be on the beach, within a 5-minute walk of Grand Cayman Beaches and North Sound.
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
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 Babylon (Dive Site).
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 AU$256 per night from 1 Jan to 2 Jan
AU$256
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at this vacation home in George Town, you'll be a 3-minute drive from Grand Cayman Beaches and 9 minutes from Port of Georgetown.
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.

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
242 Holiday Homes
Lowest Price
AU$256
Highest Price
AU$1,286
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 Grand Cayman

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
Fully refundableReserve now, pay when you stay
The price is AU$698 per night from 13 Jan to 14 Jan
AU$698
13 Jan - 14 Jan 2026
includes taxes & fees
When you stay at Hampton by Hilton Grand Cayman Seven Mile Beach in Seven Mile Beach, you'll be on the beach, within a 5-minute drive of Camana Bay and Port ...
Opens in a new windowHampton by Hilton Grand Cayman Seven Mile Beach
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$933 per night from 6 Jan to 7 Jan
AU$933
6 Jan - 7 Jan 2026
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 5-minute walk of Seven Mile Beach and Grand Cayman ...
Opens in a new windowHotel Indigo Grand Cayman by IHG
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 AU$1,286 per night from 4 Jan to 5 Jan
AU$1,286
4 Jan - 5 Jan 2026
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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The Grove

The Grove

5 out of 5
1350 W Bay Rd Seven Mile Beach West Bay
When you stay at The Grove in Seven Mile Beach, you'll be next to a golf course, just steps from Seven Mile Beach and 8 minutes by foot from Grand Cayman ...
Opens in a new windowThe Grove
Don't see what you're looking for?
See all available properties in Grand Cayman
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.