Book Holiday Homes in Grand Cayman

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Featured Holiday Homes in Grand Cayman

Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
The price is AU$275 per night from 1 Apr to 2 Apr
AU$275
includes taxes & fees
1 Apr - 2 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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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
Caymanian Style Home
w/ Pool, Pickle Ball Court, Optional Private Bar

Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Rumpoint
With a stay at this vacation home in North Side, you'll be by the sea, just a 1-minute walk from North Sound and 11 minutes by foot from Grand Cayman ...
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar
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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
244 Holiday Homes
Lowest Price
AU$275
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!, 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, Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Top trending hotels in Grand Cayman

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$905 per night from 30 Apr to 1 May
AU$905
includes taxes & fees
30 Apr - 1 May
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$947 per night from 30 Apr to 1 May
AU$947
includes taxes & fees
30 Apr - 1 May
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$575 per night from 19 Apr to 20 Apr
AU$575
includes taxes & fees
19 Apr - 20 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 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.

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^Subject to availability and chosen travel dates.