Cayman Islands holiday homes

We found 1,361 holiday rentals — enter your dates for availability

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July 2025

August 2025

Popular Cayman Islands destinations on Bookabach

Holiday rentals with weekly discounts - Cayman Islands

Showing deals for:10 Oct - 17 Oct

Exceptional

(41 reviews)

Stunning 2BR beachfront condo

West Bay, Grand Cayman

8% off

NZ$709 per night

includes taxes & fees

Exceptional

(20 reviews)

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

North Side, Cayman Islands

8% off

NZ$580 per night

includes taxes & fees

Large Deck and Pool Overlooking Caribbean Sea

Exceptional

(6 reviews)

BeachPlumVilla - Snorkeler's Paradise

North Side

7% off

NZ$1,706 per night

includes taxes & fees

Gardens, trees, pool, and the beach…. Peaceful surroundings.

Exceptional

(23 reviews)

20 Steps to the Beach -SUMMER DISCOUNT-

North Side, Cayman Islands

5% off

NZ$697 per night

includes taxes & fees

Exceptional

(8 reviews)

Andy's Inn is a delightful 3 bedroom guesthouse nestled in historic Bodden Town.

Bodden Town

8% off

NZ$828 per night

includes taxes & fees

Exceptional

(49 reviews)

Champagne Sunrise - Beachfront, Sunsets,Snorkel,Swim,Pool, walk to RumPoint

North Side, Grand Cayman

8% off

NZ$1,212 per night

includes taxes & fees

Exceptional

(50 reviews)

GOOD VIBES Botanical, Boho meet the Beach ,secluded beach with ocean views

North Side

8% off

NZ$625 per night

includes taxes & fees

Exceptional

(19 reviews)

Spacious Open Concept Large family house with 3 bedrooms. Amazing space.

Bodden Town

12% off

NZ$460 per night

includes taxes & fees

Exceptional

(59 reviews)

Savhaven - 4 Bed, 4 Bath with Pool, Sleeps 8 (2 minutes away from Spotts Beach)

Savannah, Bodden Town

8% off

NZ$959 per night

includes taxes & fees

Exceptional

(55 reviews)

Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!

West End, Cayman Brac

11% off

NZ$460 per night

includes taxes & fees

Exceptional

(16 reviews)

Luxury Designer Cayman Seven Mile Beach Townhouse Condo-Direct Walk-out to Beach

Seven Mile Beach, Grand Cayman

8% off

NZ$2,153 per night

includes taxes & fees

Exceptional

(9 reviews)

Modern Condo - Seven Mile Beach - Cayman Islands - Walk Everywhere

Seven Mile Beach, George Town

8% off

NZ$765 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Find properties near top attractions in Cayman Islands

Seven Mile Beach

Port of Georgetown

Stingray City

Governor's Beach

Grand Cayman Beaches

Find the best place to stay - Cayman Islands

Nicest views on the island. Taken from peak of roof while installing a new one

Secluded Waterfront Single Family Villa with Private Pool – 3,000 Sq of Luxury

Sleeps 8 · 3 bedrooms · 3 bathrooms

Steps to the Beach! 2bed/2.5bath condo - Seabreeze Villas

Sleeps 8 · 2 bedrooms · 2+ bathrooms

The peace and tranquility of this cottage Works Wonders on the soul....

Sleeps 10 · 4 bedrooms · 3 bathrooms

The Pink Beach House boasts an expansive deck and pool directly on the Caribbean

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Sleeps 6 · 3 bedrooms · 3+ bathrooms

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Sleeps 6 · 3 bedrooms · 2 bathrooms

Frequently asked questions

What is the best area to stay in Cayman Islands when booking a holiday home?

One of the most desired areas to get a Cayman Islands holiday home is Old Man Bay. When you lock in a Bookabach holiday home, you'll enjoy having the entire place to yourselves. That means you don't have to share it with anybody apart from your group.

What is the most popular type of holiday home accommodation in Cayman Islands?

The most in-demand types of holiday homes in Cayman Islands are condos. Want something different? Bookabach has a variety of options to match the diverse needs of our guests, so you'll see holiday homes in lots of shapes and sizes. The perfect home away from home is waiting for you --- get hold of yours today.

How much does it cost to rent a holiday home in Cayman Islands?

Season, length of stay and property type are among the factors that can determine the price of a holiday home. Simply click on your travel dates to find the ultimate escape. From quaint country cottages to plush villas, all Bookabach holiday homes provide incredible value.

How much does it cost to rent a beach house in Cayman Islands?

When you travel and the style and size of the property will determine the cost of your beachside holiday home. Type in your Cayman Islands travel dates to view your available options on Bookabach. Did someone just say "private pool"? Use the filters to choose the features and amenities you need.

What are popular home amenities in Cayman Islands?

When it comes to home amenities that people are on the lookout for in Cayman Islands, a fridge, a microwave oven and off-street parking options are at the top of the list. With Bookabach holiday homes, you'll enjoy choices to suit your style and taste, whether you're taking a trip with friends, family or even pets.

Are there large group holiday homes in Cayman Islands?

With 137 properties that can host 10 or more guests in Cayman Islands, you won't have to cross anyone off the invite list. From family holidays to special events like anniversary parties and weddings, Bookabach will help you find a large group home to suit the occasion.

What are the top attractions for families in Cayman Islands?

Keeping the kids amused during your Cayman Islands holiday is a snap with these top family-friendly attractions:

Stingray City
Seven Mile Beach
Camana Bay

Can I find two-bedroom holiday homes in Cayman Islands?

Cayman Islands has 354 two-bedroom properties to pick from. Find a holiday home with all the space and comfort you're looking for at a price that's hard to resist on Bookabach.

Are there holiday homes with WiFi in Cayman Islands?

You can pick from 421 holiday homes with WiFi in Cayman Islands. If you'd like to disconnect from daily life on your holiday, but still need to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Bookabach.

How old do you have to be to rent a holiday home in Cayman Islands?

The minimum age is usually 16, 18 or 21. It can differ across properties on Bookabach, so check the rules of your preferred Cayman Islands holiday home before booking.

How long can I rent a holiday home in Cayman Islands for?

It all depends on the Cayman Islands property. To browse available options offering extended stays, simply enter your travel dates and guest number into Bookabach. You can enjoy having the property to yourself, along with the comforts of home like air conditioning, a kitchen and an outdoor space where the little ones can play. Be on the lookout for long-term stays that offer weekly or monthly discounts.