Book Holiday Homes in Little Cayman

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Featured Holiday Homes in Little Cayman

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 Bamboo Bay and Cio's Craig (Wilderness Wall).
Opens in a new windowBeach Front Paradise Home. Luxurious Funishings!
Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

Cayman Brac
When you stay at this vacation home in West End, you'll be on the beach, within a 5-minute drive of Cio's Craig (Wilderness Wall) and Bat Cave.
Opens in a new windowSouthern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!
Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

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

Stake Bay
With a stay at this vacation home in West End, you'll be on the beach, just steps from Bamboo Bay and a 3-minute drive from Cayman Brac Museum.
Opens in a new windowLuxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool
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Featherstone - The Estate

Featherstone - The Estate

Tibbett's Turn
Located in Tibbett's Turn, this vacation home is on the waterfront, within a 5-minute drive of Bamboo Bay and Cio's Craig (Wilderness Wall).
Opens in a new windowFeatherstone - The Estate
PLEASE COME AND RELAX ON OUR PRIVATE BEACH!

PLEASE COME AND RELAX ON OUR PRIVATE BEACH!

Cayman Brac
With a stay at this vacation home in Spot Bay, you'll be on the beach, just a 4-minute walk from Lighthouse Footpath and 8 minutes by foot from Long Beach.
Opens in a new windowPLEASE COME AND RELAX ON OUR PRIVATE BEACH!
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 5-minute drive of Cio's Craig (Wilderness Wall) and Bat Cave.
Opens in a new windowLuxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
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
Located in West End, this vacation home is by the sea, within a 15-minute walk of Bamboo Bay and Charlie's Reef.
Opens in a new windowNature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5
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
With a stay at this vacation home in West End, you'll be on the beach, just a 4-minute walk from Westerly Ponds and 8 minutes by foot from MV Captain Keith Tibbetts ...
Opens in a new windowPrivate 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!
Awesome Sea Views! Secluded Beach

Awesome Sea Views! Secluded Beach

Little Cayman Island
This beach vacation home is 1.2 mi (1.9 km) from National Trust Visitors Centre and 1.9 mi (3 km) from Booby Pond Nature Reserve.
Opens in a new windowAwesome Sea Views! Secluded Beach
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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
Beach Front Paradise Home. Luxurious Funishings!, Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!, Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool , Featherstone - The Estate, PLEASE COME AND RELAX ON OUR PRIVATE BEACH!, Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!, Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5, Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!, Awesome Sea Views! Secluded Beach

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 beach, just steps from Little Cayman Beach and Booby Pond Nature Reserve.
Opens in a new windowConch Club Cottage
Beachfront Villa with amazing views- Private pool/Wifi.

Beachfront Villa with amazing views- Private pool/Wifi.

Head o Bay
When you a stay at this vacation home in Little Cayman, you'll be on the beach, just steps from Owen Island Beach and South Hold Sound.
Opens in a new windowBeachfront Villa with amazing views- Private pool/Wifi.
Little Cayman Escape - Stunning  Views and Privacy - Call Cayman Villas!

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

Little Cayman
Located in Little Cayman, this villa is by the ocean, within a 15-minute drive of Point of Sand Beach and National Trust Visitors Centre.
Opens in a new windowLittle Cayman Escape - Stunning Views and Privacy - Call Cayman Villas!
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Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.

Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.

Little Cayman
With a stay at this villa in Little Cayman, you'll be on the beach, just a 1-minute walk from Owen Island Beach and 6 minutes by foot from Booby Pond Nature ...
Opens in a new windowBlossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.
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.