Photo by Cayman Islands Department of Tourism

Cayman Islands holiday homes

We found 1,388 holiday rentals — enter your dates for availability

Popular Cayman Islands destinations on Bookabach

Holiday rentals with weekly discounts – Cayman Islands

Showing deals for:13 Nov - 20 Nov

Interior
Exterior detail
Room
Living area
Exceptional
(113 reviews)

Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove

George Town

8% off
NZ$2,441
for 7 nights, 1 apartment
NZ$349 per night
includes taxes & fees
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
Property grounds
Living area
Pool
Relax in the screend in porch
Exceptional
(65 reviews)

Beach Front Paradise Home. Luxurious Funishings!

Tibbett's Turn

8% off
NZ$5,341
for 7 nights, 1 home
NZ$763 per night
includes taxes & fees
Beach Front Paradise Home. Luxurious Funishings!
Exterior
Interior
Property grounds
Room
Exceptional
(27 reviews)

Serenity On The Bay2 - Two Bed Cayman Brac - Airport Shops Restaurants Close!

West End

8% off
NZ$2,546
for 7 nights, 1 room
NZ$364 per night
includes taxes & fees
Serenity On The Bay2 - Two Bed Cayman Brac - Airport Shops Restaurants Close!
Dining
Room
Living area
Outdoor dining
Exceptional
(11 reviews)

Beachside Boutique Villa Steps to Seven Mile Beach

West Bay

8% off
NZ$3,632
for 7 nights, 1 villa
NZ$519 per night
includes taxes & fees
Beachside Boutique Villa Steps to Seven Mile Beach
Interior
patio view
Room
Private kitchen
Exceptional
(31 reviews)

Beachfront Kaibo Condo

North Side

5% off
NZ$5,178
for 7 nights, 1 apartment
NZ$740 per night
includes taxes & fees
Beachfront Kaibo Condo
Living area
Property grounds
Pool
Beach
Exceptional
(8 reviews)

BEACHFRONT RELAXATION IN LITTLE CAYMAN

Little Cayman

8% off
NZ$7,489
for 7 nights, 1 apartment
NZ$1,070 per night
includes taxes & fees
BEACHFRONT RELAXATION IN LITTLE CAYMAN
Screen Lanai
View From Condo
View from Bedroom
Great Snorkeling
Exceptional
(94 reviews)

Paradise Found Oceanfront Condo - Flexible Cancellation

North Side

8% off
NZ$2,928
for 7 nights, 1 apartment
NZ$418 per night
includes taxes & fees
Paradise Found Oceanfront Condo - Flexible Cancellation
Private kitchen
SC 104 Deck Oceanview
SC 104 Master BR
Pool
Exceptional
(68 reviews)

Cayman Famous Seven Mile Beach Sunset Cove corner unit-RIGHT ON BEACH STEPS AWAY

Seven Mile Beach

8% off
NZ$8,359
for 7 nights, 1 apartment
NZ$1,194 per night
includes taxes & fees
Cayman Famous Seven Mile Beach Sunset Cove corner unit-RIGHT ON BEACH STEPS AWAY
Comfortable queen bedroom with vanity area — practical for couples, solo travellers, or getting ready with ease.
SEVEN MILE BEACH. Lots of eateries and bars along the length.
Property grounds
CEMETERY BEACH near us. Pristine, Quiet, One of the Safest Beach Spots.
Exceptional
(18 reviews)

S1 BP | Steps to Beach | New A/C

West Bay

11% off
NZ$3,347
for 7 nights, 1 apartment
NZ$478 per night
includes taxes & fees
S1 BP | Steps to Beach | New A/C
Expansive Kitchen Island
Beach
Terrace/patio
Dining
Exceptional
(5 reviews)

7 Mile Beach Condo with Pool View and Rooftop

West Bay

5% off
NZ$19,792
for 7 nights, 1 apartment
NZ$2,827 per night
includes taxes & fees
7 Mile Beach Condo with Pool View and Rooftop
Dining
Interior
Private kitchen
Room
Exceptional
(35 reviews)

Ocean/Beachfront - stunning views! Seabreeze Villas

Bodden Town

8% off
NZ$5,018
for 7 nights, 1 apartment
NZ$717 per night
includes taxes & fees
Ocean/Beachfront - stunning views! Seabreeze Villas
Kaibo restaurant/beach bar/coffee shop/water taxi/boat marina located amile away
Starfish Point  2 miles away from condo
Pool at The Retreat for guests
Master Bedroom King bed, nightstands with storage/ceiling fan/blackout curtains
Exceptional
(37 reviews)

2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach

North Side

8% off
NZ$4,924
for 7 nights, 1 apartment
NZ$703 per night
includes taxes & fees
2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach
Interior
Interior
Room
Beach
Exceptional
(24 reviews)

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

Seven Mile Beach

8% off
NZ$16,151
for 7 nights, 1 apartment
NZ$2,307 per night
includes taxes & fees
Luxury Designer Seven Mile Beachfront Condo Townhouse -Direct Walk-out to Beach!
Living area
Pool
Living area
Interior
Exceptional
(68 reviews)

Escape to Paradise – Beautiful & Budget-Friendly Condo!

North Side

8% off
NZ$3,823
for 7 nights, 1 apartment
NZ$546 per night
includes taxes & fees
Escape to Paradise – Beautiful & Budget-Friendly Condo!
View of the primary bedroom and balcony
The middle pool at the Wyndham Resort. Here's where you'll find the kiddies pool
A drones eye view of the Castaways' Cove buildings
Castaways' Cove Pool and hot tub
Exceptional
(24 reviews)

East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!

East End

8% off
NZ$3,810
for 7 nights, 1 apartment
NZ$544 per night
includes taxes & fees
East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!
Beach hop to nearby Rum Point
...with an infinity pool...
...or marvel at the beauty of native plants in the nearby botanical garden
Prepare your morning coffee overlooking tranquil waves
Exceptional
(94 reviews)

Beachfront 1st Floor Condo - Step off your patio and into paradise!

East End

8% off
NZ$4,808
for 7 nights, 1 apartment
NZ$687 per night
includes taxes & fees
Beachfront 1st Floor Condo - Step off your patio and into paradise!
Kitchen with huge island.
Beach
Pool
Most amazing rooftop.
Exceptional
(68 reviews)

7 Mile Luxury Beach Club. Ocean views from Roof Terrace and Pool Pavilion.

West Bay

5% off
NZ$15,898
for 7 nights, 1 apartment
NZ$2,271 per night
includes taxes & fees
7 Mile Luxury Beach Club. Ocean views from Roof Terrace and Pool Pavilion.
Front porch, with deck chairs & sun loungers. Dining table has been replaced with a 9-foot solid wood outdoor table with 6 chairs!
SEVEN MILE BEACH. Lots of eateries and bars along the length.
Living area
CAR RENTALS available! Simply book in advance on your Guest Portal.
Exceptional
(5 reviews)

S2 BP | Steps to Beach

West Bay

7% off
NZ$4,243
for 7 nights, 1 apartment
NZ$606 per night
includes taxes & fees
S2 BP | Steps to Beach

Why visit Cayman Islands

  • Pristine Beaches: Enjoy sun, surf, and sand on the stunning shores of the Cayman Islands.
  • Rich Cultural Heritage: Discover museums and historical sites that celebrate the vibrant local culture.
  • Natural Wonders: Explore fascinating caves and lush landscapes perfect for outdoor adventures.
  • Family-Friendly Atmosphere: Ideal for families with a mix of relaxation and exciting excursions.
  • Caribbean Vibe: Experience the laid-back, colourful spirit that makes the Cayman Islands unique.

Top attractions in Cayman Islands

The Cayman Islands offers a stunning array of attractions perfect for beach lovers, families, and outdoor enthusiasts. Explore beautiful beaches, fascinating caves, and rich historical museums that showcase the vibrant culture of the islands. Whether you're seeking relaxation by the shore or adventurous outings, the Cayman Islands promises unforgettable experiences that cater to every traveller's interests.

  • Seven Mile Beach: Enjoy the pristine sandy stretch with its inviting beach vibes, perfect for sunbathing, swimming, and local water sports.
  • National Gallery of the Cayman Islands: Immerse yourself in vibrant local art and culture at this renowned gallery, featuring diverse exhibits that capture the island's creative spirit.
  • East End Lighthouse: Discover a piece of Cayman Islands history with this historic lighthouse, offering cultural insights and picturesque views of the rugged coastline.

Things to do recommended for couples

Ready for a romantic getaway in the Cayman Islands? Enjoy a sunset dinner on Seven Mile Beach, explore the enchanting underwater world while snorkelling together, and take a leisurely stroll through the vibrant local markets. It's the perfect destination for couples seeking unforgettable experiences.

Things to do recommended for families

Families visiting the Cayman Islands can have a fantastic time at the Cayman Turtle Centre, where kids can learn about sea turtles and even snorkel with them. The beautiful Seven Mile Beach offers safe swimming and plenty of family-friendly dining options, making it a perfect day out for everyone.

Things to do recommended for groups

Discover the vibrant local culture in the Cayman Islands with group activities such as exploring hidden beaches and sampling island cuisine, perfect for a Kiwi holiday experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Cayman Islands

Whether you’re travelling with a group, as a family, with your pets, or looking for longer stays, be sure to sort your search using the right filters. Here are some helpful tips for booking on Vrbo.

  • Traveling to Cayman Islands with a group: Consider how many bedrooms you'll require, as well as amenities like a fully equipped kitchen or an outdoor area for group gatherings. Luckily, you can filter for all these features—and many more—on Vrbo.
  • Traveling to Cayman Islands with young kids: Travelling with young children can be quite demanding. It's essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cayman Islands: For many, a family holiday isn’t complete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Cayman Islands: If you're after holiday rentals offering deals for month-long stays or more, you've come to the right spot. By applying the right filter, you can effortlessly discover and save on monthly rentals. Think about including a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Cayman Islands

Discover the charm of the Cayman Islands, where stunning sandy beaches and a laid-back Caribbean vibe await. Enjoy a family-friendly retreat with plenty of outdoor adventures, from romantic seaside strolls to exciting excursions. Whether you’re in search of a peaceful getaway or a vibrant local scene, the Cayman Islands offer a perfect blend of relaxation, recreation, and natural beauty, ensuring an unforgettable holiday experience for everyone.

  • Grand Cayman: Grand Cayman is a naturally stunning island within the Cayman Islands, celebrated for its pristine beaches and family-friendly outdoor activities. Visitors can enjoy leisurely days on the sandy shores and explore diverse shopping areas and malls, all while experiencing the island’s rich natural offerings. Notable attractions include expansive beaches, a theme park, and a film studio, creating a blend of relaxation and entertainment perfect for a memorable holiday.
  • Seven Mile Beach: Seven Mile Beach is a vibrant city on the Cayman Islands, known for its extensive sandy coastline and outdoor charm. This destination is ideal for families and beach enthusiasts, offering easy access to shopping areas, resort-style experiences, and bustling shopping mall centres. The locale is further enhanced by its famous beach, a lively marina, and a dedicated tourist precinct, ensuring a well-rounded travel experience.
  • North Side: North Side is a dynamic district in the Cayman Islands, offering a mix of beachside leisure and adventurous pursuits. It is a perfect destination for those seeking both relaxation and a touch of excitement, with plenty of shopping areas, opportunities for adventure activities, and underwater sports. The district is well-known for its scenic beach, attractive marina, and a vibrant tourist precinct, making it a versatile choice for any traveller.

Best time to go to Cayman Islands

If you're planning a trip to Cayman Islands, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January78.4°F (25.8°C)No Rain (Dry)Mostly SunnySlightly High
February78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverage
March78.4°F (25.8°C)No Rain (Dry)Mostly SunnySlightly High
April80.2°F (26.8°C)No Rain (Dry)Mostly SunnyAverage
May81.7°F (27.6°C)Light RainMostly SunnySlightly Low
June82.9°F (28.3°C)Light RainMostly SunnyAverage
July83.8°F (28.8°C)Light RainMostly SunnySlightly High
August84.4°F (29.1°C)Light RainMostly SunnyAverage
September84.2°F (29.0°C)Light RainMostly SunnyAverage
October83.1°F (28.4°C)Moderate RainMostly SunnySlightly Low
November81.3°F (27.4°C)Light RainMostly SunnySlightly Low
December79.9°F (26.6°C)No Rain (Dry)Mostly SunnyAverage

Booking with Vrbo is simple

Are you aiming to save on your next adventure? Being flexible with your travel dates can lead to significant savings, as prices can vary quite a bit. Additionally, opting for a longer stay often allows for greater discounts. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental. Happy travels.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a handy platform for planning your journeys, allowing you to create new trips, manage your existing plans, and keep track of your bookings. The properties you've saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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.

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