Cayman Islands vacation rentals

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Latest Cayman Islands vacation rental deals

MOST POPULARGeorge Town
Vacation homes from $129
West Bay
Vacation homes from $180

Best Cayman Islands vacation rentals

Most recommended vacation rentals in the Cayman Islands

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Slice of Paradise- 2 mins from Spotts Beach! - George Town - Balcony
Slice of Paradise- 2 mins from Spotts Beach!
George Town, Cayman Islands
Free Wi-Fi
$158+
Check availability
Sanctuary Cove at the Careenage Grand Harbour. 2 Queen bed - 2 bath with pool. - George Town - Building
Sanctuary Cove at the Careenage Grand Harbour. 2 Queen bed - 2 bath with pool.
George Town, Cayman Islands
$472+
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Little Cayman 3 Bedroom Oceanfront Private Villa - Little Cayman - Beach
Little Cayman 3 Bedroom Oceanfront Private Villa
Little Cayman, Cayman Islands
Free Wi-Fi
$673+
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Lovely Sea Dreams Villa with Private Beach and Deck! - Cayman Brac - Balcony
Lovely Sea Dreams Villa with Private Beach and Deck!
Cayman Brac, Cayman Islands
9.9Wonderful(9)
Free Wi-Fi
$264+
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Timeless - Beautiful 4 bedroom home on the north coast of Little Cayman. - Little Cayman - Beach
Timeless - Beautiful 4 bedroom home on the north coast of Little Cayman.
Little Cayman, Cayman Islands
$1,270+
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Featherstone Cottage, Cayman Brac - Cayman Brac
Featherstone Cottage, Cayman Brac
Cayman Brac, Cayman Islands
9.0Wonderful(1)
Parking
Free Wi-Fi
Pool
Pet friendly
$345+
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A fantastic two bedroom condo - close to everything! - Little Cayman - Living room
A fantastic two bedroom condo - close to everything!
Little Cayman, Cayman Islands
$476+
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Southern Exposure, Secluded New Beach House On Cayman Brac! Divers Delight! - Cayman Brac - Beach
Southern Exposure, Secluded New Beach House On Cayman Brac! Divers Delight!
Cayman Brac, Cayman Islands
Free Wi-Fi
$217+
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Razorbrac Seaesta - Private Beachfront Home - Cayman Brac - Beach
Razorbrac Seaesta - Private Beachfront Home
Cayman Brac, Cayman Islands
Free Wi-Fi
$184+
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Newly Built Beach House Footsteps From The Water - Cayman Brac - Living room
Newly Built Beach House Footsteps From The Water
Cayman Brac, Cayman Islands
Free Wi-Fi
$298+
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The Sanctuary - Unforgettable 4-Bedroom Little Cayman Villa Perfect for Retreats - Little Cayman - Balcony
The Sanctuary - Unforgettable 4-Bedroom Little Cayman Villa Perfect for Retreats
Little Cayman, Cayman Islands
$2,396+
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Brac Beach House Oceanfront! Amazing Views! Dive Snorkel, Kayak, Hammocks, Relax - Cayman Brac - Balcony
Brac Beach House Oceanfront! Amazing Views! Dive Snorkel, Kayak, Hammocks, Relax
Cayman Brac, Cayman Islands
Free Wi-Fi
$302+
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It's time to take a break and escape to your own Private Paradise! - Cayman Brac - Beach
It's time to take a break and escape to your own Private Paradise!
Cayman Brac, Cayman Islands
Pool
$278+
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Northeast Bay Escape in quiet Cayman Brac - Cayman Brac - Beach
Northeast Bay Escape in quiet Cayman Brac
Cayman Brac, Cayman Islands
Pet friendly
$340+
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A Little Piece of Tropical Paradise With Inground Pool - Cayman Brac - Pool
A Little Piece of Tropical Paradise With Inground Pool
Cayman Brac, Cayman Islands
Free Wi-Fi
Pool
$341+
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Please Come And Relax On Our Private Beach! - Cayman Brac - Beach
Please Come And Relax On Our Private Beach!
Cayman Brac, Cayman Islands
$223+
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Property Types

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

October

High season

December

Average price (weeknight)

$646

Average price (weekend night)

$714
Cheapest month to stay with an average 52% drop in price.
Most expensive month to stay with an average 76% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Cayman Islands vacation rental

  • If you’re looking for a cheap vacation rental in the Cayman Islands, you should consider visiting during the low season. The cheapest vacation homes in the Cayman Islands can be found in October and September.
  • The cheapest night for renting a vacation home in the Cayman Islands is Friday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in the Cayman Islands for 5 days.
  • The cheapest the Cayman Islands vacation rental found on KAYAK in the last 2 weeks was $439, while the most expensive was $925.
  • Beachfront, pool, air-conditioned, and adults only are the most popular vacation rental property amenities in the Cayman Islands
  • Vacation rentals in the Cayman Islands are around 108% cheaper than hotels on average. Search here to compare prices for all accommodation types in the Cayman Islands.
  • Sister Islands is the region in the Cayman Islands with the most affordable vacation rental properties, with around 62 properties and an average price of $373 per night. The most popular vacation homes in Sister Islands are Little Cayman 3 Bedroom Oceanfront Private Villa, Lovely Sea Dreams Villa with Private Beach and Deck!, and Timeless - Beautiful 4 bedroom home on the north coast of Little Cayman..
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FAQs when booking a vacation home in the Cayman Islands

  • What is the most popular vacation rental destination in the Cayman Islands?

    Based on KAYAK vacation rental searches, the most popular destination is George Town (55% of total searches to the Cayman Islands). The next most popular destinations are West Bay (16%) and North Side (9%). Searches for vacation rentals in Cayman Brac (7%), East End (7%) and Little Cayman (6%) are also popular.

  • How much is a vacation rental in the Cayman Islands for tonight?

    In the last 72 hours, users have found the Cayman Islands vacation rentals for tonight for as low as $170. Search here for similar prices

  • How much is a vacation rental in the Cayman Islands for this weekend?

    In the last 72 hours, users have found the Cayman Islands vacation rentals for this weekend for as low as $221 per night. Search here for similar prices

  • How much is a vacation rental for a week in the Cayman Islands?

    The average price for a weekly the Cayman Islands vacation rental found by KAYAK users in the last 2 weeks is $2,702.

  • How much is a vacation rental for a month in the Cayman Islands?

    The average price for a monthly the Cayman Islands vacation rental found by KAYAK users in the last 2 weeks is $11,581.

  • What types of vacation rentals are available in the Cayman Islands?

    There are loads of different property types that you can make your vacation home in the Cayman Islands. You’ll find apartments, condos, houses, villas, cottages and homestays.

  • What are some of the most-loved vacation rentals available in the Cayman Islands?

    There are many types of properties available for the Cayman Islands vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Cayman Luxury Rentals at The Grove and The Grandview Condos on Seven Mile Beach.

  • Are there any pet-friendly vacation rentals in the Cayman Islands?

    There are a number of dog and pet-friendly the Cayman Islands vacation rentals, with around 4% allowing you to bring your pet along with you.

  • What are the most popular regions of the Cayman Islands for vacation rentals?

    Based on KAYAK vacation rental searches, the most popular region to stay in the Cayman Islands is George Town. Other popular choices include West Bay and East End.

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Where to stay in the Cayman Islands?

Our map will help you find the perfect place to stay in the Cayman Islands by showing you the exact location of each vacation home.

Everything you need to know for your stay in the Cayman Islands

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