Book Holiday Homes in Little Cayman

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Featured Holiday Homes in Little Cayman

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

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

North Side, West End Cayman Brac
Stay at this beach holiday home in West End. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions West End Point Outlook and MV Captain Keith Tibbetts ...
Opens in a new windowPrivate 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!
PLEASE COME AND RELAX ON OUR PRIVATE BEACH!

PLEASE COME AND RELAX ON OUR PRIVATE BEACH!

Cayman Brac
Stay at this beach holiday home in Spot Bay. Enjoy a beach locale, laundry facilities and patios. Popular attractions Lighthouse Footpath and Peter's Cave are ...
Opens in a new windowPLEASE COME AND RELAX ON OUR PRIVATE BEACH!
Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5

Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5

Cayman Brac Cayman Brac
Stay at this holiday home in West End. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Popular attractions Charlie's Reef and Rebecca's Cave are located ...
Opens in a new windowNature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5
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The ROCK HOUSE with Private Beach on Little Cayman

The ROCK HOUSE with Private Beach on Little Cayman

Blossom Village Sister Islands
Stay at this holiday home in Little Cayman. Enjoy a beach locale. Popular attractions National Trust Visitors Centre and Little Cayman Beaches are located ...
Opens in a new windowThe ROCK HOUSE with Private Beach on Little Cayman
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Cayman Brac Sister Islands
Stay at this beach holiday home in West End. Enjoy free Wi-Fi, a beach locale and breakfast (surcharge). Popular attractions Cayman Brac Beaches and Cio's Craig ...
Opens in a new windowLuxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
Ocean view from every room ,quiet neighborhood family friendly.Bluff view

Ocean view from every room ,quiet neighborhood family friendly.Bluff view

Cayman Brac Sister Islands
Stay at this holiday home in East End. Enjoy laundry facilities and air conditioning. Popular attractions Conch Rock and National Trust Parrot Reserve are located ...
Opens in a new windowOcean view from every room ,quiet neighborhood family friendly.Bluff view
Beach Front Paradise Home.  Luxurious Funishings!

Beach Front Paradise Home. Luxurious Funishings!

Cayman Brac Cayman Islands
Stay at this beach holiday home in Tibbett's Turn. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Cayman Brac Beaches and Cio's Craig ...
Opens in a new windowBeach Front Paradise Home. Luxurious Funishings!
Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Stake Bay Cayman Brac
Stay at this beach holiday home in West End. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Cayman Brac Beaches and Cayman Brac Museum ...
Opens in a new windowLuxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool
Little Cayman 3 Bedroom Oceanfront  Private Villa

Little Cayman 3 Bedroom Oceanfront Private Villa

West End Little Cayman
Stay at this holiday home in Little Cayman. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Salt Rocks Nature Trail North Trailhead and ...
Opens in a new windowLittle Cayman 3 Bedroom Oceanfront Private Villa
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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.

Little Cayman 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 Little Cayman vacation homes are the perfect way for you to wing it.

Holiday houses in Little Cayman 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 Little Cayman 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 Little Cayman adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Little Cayman 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 Little Cayman 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.

Little Cayman Holiday Homes essential information

Accommodation
19 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!, PLEASE COME AND RELAX ON OUR PRIVATE BEACH!, Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5, The ROCK HOUSE with Private Beach on Little Cayman, Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!, Ocean view from every room ,quiet neighborhood family friendly.Bluff view , Beach Front Paradise Home. Luxurious Funishings!, Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool , Little Cayman 3 Bedroom Oceanfront Private Villa

Top trending hotels in Little Cayman

The ROCK HOUSE with Private Beach on Little Cayman

The ROCK HOUSE with Private Beach on Little Cayman

Blossom Village Sister Islands
Stay at this holiday home in Little Cayman. Enjoy a beach locale. Popular attractions National Trust Visitors Centre and Little Cayman Beaches are located ...
Opens in a new windowThe ROCK HOUSE with Private Beach on Little Cayman
Little Cayman Escape - Stunning  Views and Privacy - Call Cayman Villas!

Little Cayman Escape - Stunning Views and Privacy - Call Cayman Villas!

Little Cayman Little Cayman
Stay at this beach villa in Little Cayman. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Point of Sand Beach and National Trust ...
Opens in a new windowLittle Cayman Escape - Stunning Views and Privacy - Call Cayman Villas!
Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.

Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.

Little Cayman Little Cayman
Stay at this beach villa in Little Cayman. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Little Cayman Museum and Little Cayman ...
Opens in a new windowBlossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.
Save an average of 15% on thousands of hotels when you're signed in
Conch Club Cottage

Conch Club Cottage

3 out of 5
1200 Guy Banks Road Little Cayman Cayman Islands
Stay at this beach hotel in Little Cayman. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions South Hold Sound and Booby Pond Nature Reserve ...
Opens in a new windowConch Club Cottage
Don't see what you're looking for?
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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.

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^Subject to availability and chosen travel dates.