Book Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

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
Book a stay at this beach vacation home in North Side. Enjoy private pools, a beach locale, and a garden. Popular attractions Grand Cayman Beaches and Cayman ...
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes

Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes

Rum Point
Book a stay at this beach vacation home in North Side. Enjoy a beach locale, a water park, and patios. Popular attractions Rum Point Beach and Cayman Kai Public ...
Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes
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
Book a stay at this beach vacation home in East End. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Colliers Public Beach and East End ...
Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock
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Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
The price is NZ$300 per night from 28 Jan to 29 Jan
NZ$300
includes taxes & fees
28 Jan - 29 Jan
Stay at this vacation home in George Town. Enjoy free WiFi, a garden, and patios. Popular attractions Port of Georgetown and Spotts Beach are located ...
Slice of Paradise- 2 mins from Spotts Beach!
Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas

Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas

North Side
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Mastic Trail North Trailhead and Grand ...
Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas
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
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Cayman Kai Public Beach and Star ...
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
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
Book a stay at this beach vacation home in East End. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Queen Elizabeth II Botanic Park ...
The peace and tranquility of this cottage Works Wonders on the soul....
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
Book a stay at this beach vacation home in North Side. Enjoy private pools, a beach locale, and a garden. Our guests praise the helpful staff in our reviews. ...
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

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

Grand Cayman
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Star Fish Point and Starfish Beach ...
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
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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
NZ$300
Highest Price
NZ$2,336
Popular accommodation
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point, Villa on Bioluminescent Bay, short walk to Rum Point beach, Free Kayaks, 4 bikes, Stepping Stone / 4 BR East End Luxury Ocean & Beach Front Pool Villa w/ Dock, Slice of Paradise- 2 mins from Spotts Beach!, Mahogany Point 3 – A Beachfront Townhouse by Cayman Villas, Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!, The peace and tranquility of this cottage Works Wonders on the soul...., SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point , Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Top trending hotels in Cayman Islands

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 NZ$1,263 per night from 9 Feb to 10 Feb
NZ$1,263
includes taxes & fees
9 Feb - 10 Feb
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and ...
Grand Cayman Marriott Resort
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

3.5 out of 5
1240 W Bay Rd, Seven Mile Beach, Grand Cayman
The price is NZ$509 per night from 28 Jan to 29 Jan
NZ$509
includes taxes & fees
28 Jan - 29 Jan
Stay at this 3.5-star business-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and a garden. Popular attractions Port of ...
Governors Village Seven Mile Beach Corridor
Hotel Indigo Grand Cayman, an IHG Hotel

Hotel Indigo Grand Cayman, an IHG Hotel

4.5 out of 5
32 Seafire Way, Seven Mile Beach, West Bay
The price is NZ$1,219 per night from 9 Feb to 10 Feb
NZ$1,219
includes taxes & fees
9 Feb - 10 Feb
Stay at this 4.5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Port of Georgetown and Seven ...
Hotel Indigo Grand Cayman, an IHG Hotel
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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 NZ$2,336 per night from 28 Jan to 29 Jan
NZ$2,336
includes taxes & fees
28 Jan - 29 Jan
Stay at this 5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
Kimpton Seafire Resort + Spa, an IHG Hotel
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.

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