Book Holiday Homes in Little Cayman

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Featured Holiday Homes in Little Cayman

Sunsets, amazing sonkeling, seaside veranda, kayaks, bikes, fresh seafood 4U

Sunsets, amazing sonkeling, seaside veranda, kayaks, bikes, fresh seafood 4U

North Side, West End
Located in West End, this vacation home is on the beach, within a 5-minute walk of Cayman Brac Beaches and Westerly Ponds.
Sunsets, amazing sonkeling, seaside veranda, kayaks, bikes, fresh seafood 4U
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
Located in West End, this vacation home is by the ocean, within a 15-minute walk of Cio's Craig (Wilderness Wall) and Cayman Brac Beaches.
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
Beach Front Paradise Home.  Luxurious Funishings!

Beach Front Paradise Home. Luxurious Funishings!

Cayman Brac
Located in Tibbett's Turn, this vacation home is by the ocean, within a 5-minute drive of Cayman Brac Beaches and Bamboo Bay.
Beach Front Paradise Home. Luxurious Funishings!
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THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!

THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!

CAYMAND BRAC
Located in West End, this vacation home is by the ocean, within a 15-minute walk of Cio's Craig (Wilderness Wall) and Cayman Brac Beaches.
THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!
Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept

Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept

West End
With a stay at this vacation home in West End, you'll be on the beach, just a 2-minute walk from Cayman Brac Beaches and 9 minutes by foot from MV Captain Keith ...
Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept
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
With a stay at this vacation home in West End, you'll be by the sea, just a 3-minute walk from Cayman Brac Beaches and 12 minutes by foot from Bamboo Bay.
Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5
Ocean view from every room ,quiet neighborhood family friendly.Bluff view

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

Cayman Brac
Located in East End, this vacation home is a 1-minute drive from Cayman Brac Beaches and 5 minutes from Cio's Craig (Wilderness Wall).
Ocean view from every room ,quiet neighborhood family friendly.Bluff view
The ROCK HOUSE with Private Beach on Little Cayman

The ROCK HOUSE with Private Beach on Little Cayman

Blossom Village
With a stay at this vacation home in Little Cayman, you'll be a 1-minute walk from Owen Island Beach and 11 minutes by foot from National Trust Visitors ...
The ROCK HOUSE with Private Beach on Little Cayman
Featherstone - The Estate

Featherstone - The Estate

Tibbett's Turn
With a stay at this vacation home in Tibbett's Turn, you'll be on the beach, just steps from Cayman Brac Beaches and a 4-minute drive from Bamboo Bay.
Featherstone - The Estate
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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
18 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Sunsets, amazing sonkeling, seaside veranda, kayaks, bikes, fresh seafood 4U, Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!, Beach Front Paradise Home. Luxurious Funishings!, THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!, Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept, Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5, Ocean view from every room ,quiet neighborhood family friendly.Bluff view , The ROCK HOUSE with Private Beach on Little Cayman, Featherstone - The Estate

Top trending hotels in Little Cayman

Conch Club Cottage

Conch Club Cottage

3 out of 5
1200 Guy Banks Road, Little Cayman, Cayman Islands
When you a stay at Conch Club Cottage in Little Cayman, you'll be on the waterfront, just steps from Little Cayman Beach and Owen Island Beach.
Conch Club Cottage
Little Cayman Escape - Lighthouse Views of the Caribbean Sea

Little Cayman Escape - Lighthouse Views of the Caribbean Sea

Little Cayman
When you a stay at this villa in Little Cayman, you'll be on the beach, just steps from Booby Pond Nature Reserve and Cayman Brac Beaches.
Little Cayman Escape - Lighthouse Views of the Caribbean Sea
The ROCK HOUSE with Private Beach on Little Cayman

The ROCK HOUSE with Private Beach on Little Cayman

Blossom Village
With a stay at this vacation home in Little Cayman, you'll be a 1-minute walk from Owen Island Beach and 11 minutes by foot from National Trust Visitors ...
The ROCK HOUSE with Private Beach on Little Cayman
Save an average of 15% on thousands of hotels when you're signed in
Little Cayman 3 Bedroom Oceanfront  Private Villa

Little Cayman 3 Bedroom Oceanfront Private Villa

West End
With a stay at this vacation home in Little Cayman, you'll be by the ocean, just a 4-minute walk from Salt Rocks Nature Trail North Trailhead and 5 minutes by ...
Little Cayman 3 Bedroom Oceanfront Private Villa
Don't see what you're looking for?
See all available properties in Little Cayman
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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.