Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

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!
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
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!
Mahogany Point 3 – A Beachfront Townhouse on the North Coast of Grand Cayman

Mahogany Point 3 – A Beachfront Townhouse on the North Coast of Grand Cayman

North Side
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.
Mahogany Point 3 – A Beachfront Townhouse on the North Coast of Grand Cayman
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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
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
Located in North Side, this vacation home is on the beach, within a 5-minute walk of North Sound and Grand Cayman Beaches.
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Beachfront, White Sand, Turquoise Water, Bikes, Kayak, Snorkel Gear, Rum Point!!

Beachfront, White Sand, Turquoise Water, 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.
Beachfront, White Sand, Turquoise Water, Bikes, Kayak, Snorkel Gear, Rum Point!!
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Grand Cayman
When you a stay at this vacation home in North Side, you'll be on the beach, just steps from North Sound and Star Fish Point.
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
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
Reduced Summer Rates! Private oceanfront home with wrap-around screened porch

Reduced Summer Rates! Private oceanfront home with wrap-around screened porch

North Side
With a stay at this vacation home in North Side, you'll be on the waterfront, just a 4-minute walk from Babylon (Dive Site) and 6 minutes by foot from Grand ...
Reduced Summer Rates! Private oceanfront home with wrap-around screened porch
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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
228 Holiday Homes
Lowest Price
AU$858
Highest Price
AU$1,395
Popular accommodation
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, Slice of Paradise- 2 mins from Spotts Beach!, Mahogany Point 3 – A Beachfront Townhouse on the North Coast of Grand Cayman, The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point , Beachfront, White Sand, Turquoise Water, Bikes, Kayak, Snorkel Gear, Rum Point!!, Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point, Ocean Paradise, Reduced Summer Rates! Private oceanfront home with wrap-around screened porch

Top trending hotels in Cayman Islands

Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
The price is AU$1,225 per night from 7 Dec to 8 Dec
AU$1,225
includes taxes & fees
7 Dec - 8 Dec
When you stay at Kimpton Seafire Resort + Spa, an IHG Hotel in Seven Mile Beach, you'll be on the beach, within a 15-minute drive of Seven Mile Beach and Port ...
Kimpton Seafire Resort + Spa, an IHG Hotel
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$1,395 per night from 7 Dec to 8 Dec
AU$1,395
includes taxes & fees
7 Dec - 8 Dec
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
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$858 per night from 15 Dec to 16 Dec
AU$858
includes taxes & fees
15 Dec - 16 Dec
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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The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Seven Mile Beach, P.O. Box 30620, Seven Mile Beach, Grand Cayman
The price is AU$1,065 per night from 15 Dec to 16 Dec
AU$1,065
includes taxes & fees
15 Dec - 16 Dec
When you stay at The Westin Grand Cayman Seven Mile Beach Resort & Spa in Seven Mile Beach, you'll be on the waterfront, within a 5-minute drive of The Strand ...
The Westin Grand Cayman Seven Mile Beach Resort & Spa
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.