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
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!
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
The price is NZ$293 per night from 8 Dec to 9 Dec
NZ$293
includes taxes & fees
8 Dec - 9 Dec
Stay at this vacation home in George Town. Enjoy free WiFi, a garden, and patios. Popular attractions Port of Georgetown and Seven Mile Beach are located ...
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
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 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
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
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
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
Book a stay at this beach vacation home in North Side. Enjoy a beach locale and air conditioning. Popular attractions Mastic Trail North Trailhead and Babylon ...
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
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
Ocean Paradise

Ocean Paradise

4 out of 5
1234 Rum Point Road, North Side, Grand Cayman
Stay at this 4-star beach vacation home in North Side. Enjoy free WiFi, free parking, and a garden. Popular attractions Cayman Kai Public Beach and Star Fish ...
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
Stay at this vacation home in North Side. Enjoy free WiFi, a garden, and patios. Popular attractions Babylon (Dive Site) and Mastic Trail North Trailhead are ...
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
NZ$293
Highest Price
NZ$1,937
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 NZ$1,432 per night from 15 Dec to 16 Dec
NZ$1,432
includes taxes & fees
15 Dec - 16 Dec
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
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 NZ$1,937 per night from 14 Dec to 15 Dec
NZ$1,937
includes taxes & fees
14 Dec - 15 Dec
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
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 NZ$958 per night from 15 Dec to 16 Dec
NZ$958
includes taxes & fees
15 Dec - 16 Dec
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
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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 NZ$1,189 per night from 15 Dec to 16 Dec
NZ$1,189
includes taxes & fees
15 Dec - 16 Dec
Book a stay at this luxury resort in Seven Mile Beach. Enjoy a full-service spa, 6 restaurants, and a private beach. Our guests praise the helpful staff and ...
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.

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