Cayman Islands Vacation Rentals, Homes, & More

1-50 of 78 Cayman Islands Rentals

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1  2 
Resort Style Oceanfront Pool
1 / 32

Bodden Town Villa
4 Bedrooms / 4 Bathrooms / Sleeps 10

from

$922

/ night

Email Owner
1 / 7

North East Bay Cottage
1 Bedroom / 1 Bathroom / Sleeps 3

from

$136

/ night

Email Owner
Aerial of Villa Looking East
1 / 31

Bodden Town Villa
4 Bedrooms / 4 Bathrooms / Sleeps 10

from

$922

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Condo
1 / 23
Barefoot Lagoon - Island House
1 / 15

Cayman Kai Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$275

/ night

Email Owner
The Ritch Residence
1 / 16

West Bay Home
5 Bedrooms / 3.5 Bathrooms / Sleeps 14

from

$686

/ night

Email Owner
1 / 7

Rum Point Villa
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”3 Reviews

from

$287

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Condo
1 / 8

Seven Mile Beach Condo
3 Bedrooms / 2 Bathrooms / Sleeps 9

from

$295

/ night

Email Owner
Little Cayman Cayman Islands Vacation Rentals - Condo
1 / 6

Little Cayman Condo
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$400

/ night

Email Owner
South Side West End Cayman Islands Vacation Rentals - Townhouse
1 / 9

South Side West End Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$150

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Condo
1 / 16

Seven Mile Beach Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$250

/ night

Email Owner
Beautiful Cayman Beach!
1 / 3

East End Condo
1 Bedroom / 1 Bathroom / Sleeps 4

from

$172

/ night

Email Owner
7 Mile Beach - Chairs & Umbrella provided
1 / 13

Seven Mile Beach Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$155

/ night

Email Owner
Rum Point Cayman Islands Vacation Rentals - Home
1 / 35

Rum Point Home
5 Bedrooms / 5 Bathrooms / Sleeps 12

Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 9

Seven Mile Beach Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”9 Reviews

from

$330

/ night

Email Owner
Grand Cayman Cayman Islands Vacation Rentals - Villa
1 / 21

Grand Cayman Villa
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$710

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 12

Seven Mile Beach Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”10 Reviews

from

$339

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 10

Seven Mile Beach Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”1 Review

from

$309

/ night

Email Owner
Cayman Kai Cayman Islands Vacation Rentals - Apartment
1 / 12

Cayman Kai Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$291

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 13

Seven Mile Beach Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”14 Reviews

from

$475

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 8

Seven Mile Beach Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”10 Reviews

from

$330

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 8

Seven Mile Beach Apartment
1 Bedroom / 1 Bathroom / Sleeps 2

“ Excellent ”14 Reviews

from

$265

/ night

Email Owner
George Town Cayman Islands Vacation Rentals - Villa
1 / 10

George Town Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$426

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 15

Seven Mile Beach Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$458

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 10

Seven Mile Beach Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”6 Reviews

from

$264

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 11

Seven Mile Beach Home
2 Bedrooms / 3 Bathrooms / Sleeps 4

“ Excellent ”11 Reviews

from

$266

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 9

Seven Mile Beach Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$330

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 7

Seven Mile Beach Apartment
1 Bedroom / 1 Bathroom / Sleeps 2

“ Excellent ”15 Reviews

from

$265

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 11

Seven Mile Beach Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”11 Reviews

from

$264

/ night

Email Owner
West Bay Cayman Islands Vacation Rentals - Apartment
1 / 10

West Bay Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”15 Reviews

from

$227

/ night

Email Owner
Old Man Bay Cayman Islands Vacation Rentals - Apartment
1 / 17

Old Man Bay Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$284

/ night

Email Owner
Old Man Bay Cayman Islands Vacation Rentals - Apartment
1 / 12

Old Man Bay Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”15 Reviews

from

$213

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 25

Seven Mile Beach Apartment
4 Bedrooms / 5 Bathrooms / Sleeps 10

from

$923

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Villa
1 / 18

Seven Mile Beach Villa
5 Bedrooms / 5 Bathrooms / Sleeps 12

“ Excellent ”9 Reviews

Cayman Kai Cayman Islands Vacation Rentals - Apartment
1 / 15

Cayman Kai Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$426

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 8

Seven Mile Beach Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”10 Reviews

Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 9

Seven Mile Beach Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

Grand Cayman Cayman Islands Vacation Rentals - Home
1 / 16

Grand Cayman Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

Grand Cayman Cayman Islands Vacation Rentals - Home
1 / 11

Grand Cayman Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”4 Reviews

Grand Cayman Cayman Islands Vacation Rentals - Home
1 / 9

Grand Cayman Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

George Town Cayman Islands Vacation Rentals - Villa
1 / 21

George Town Villa
4 Bedrooms / 4 Bathrooms / Sleeps 10

from

$994

/ night

Email Owner
Little Cayman Cayman Islands Vacation Rentals - Villa
1 / 11

Little Cayman Villa
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”8 Reviews

from

$710

/ night

Email Owner
Little Cayman Cayman Islands Vacation Rentals - Cottage
1 / 14

Little Cayman Cottage
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”3 Reviews

from

$109

/ night

Email Owner
Little Cayman Cayman Islands Vacation Rentals - Cottage
1 / 12

Little Cayman Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$109

/ night

Email Owner
West Bay Cayman Islands Vacation Rentals - Villa
1 / 13

West Bay Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$333

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 12

Seven Mile Beach Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”12 Reviews

from

$339

/ night

Email Owner
East End Cayman Islands Vacation Rentals - Villa
1 / 16

East End Villa
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”7 Reviews

from

$538

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Home
1 / 7

Seven Mile Beach Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$330

/ night

Email Owner
Seven Mile Beach Cayman Islands Vacation Rentals - Apartment
1 / 12

Seven Mile Beach Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$379

/ night

Email Owner
1  2 

Visiting the Cayman Islands

Calm blue waters, white sand, and waving palm trees are the hallmarks of the Cayman Islands. Located south of Cuba and west of Jamaica, the Caymans are becoming the place to vacation in the Caribbean. Cayman Islands rentals are perfect for families who want the comforts of home as they explore this island paradise. Plan your dream vacation online, save money by staying in one of our by-owner Cayman Islands house rentals, and see the island through the eyes of a local!
Areas within the Cayman Islands
The Caymans consist of three islands: Grand Cayman, Cayman Brac, and Little Cayman. Grand Cayman is the largest of the three islands. Historic George Town offers fine dining and duty-free shopping among traditional Caribbean-style buildings. Cayman Brac has the most spectacular landscape of the three islands. Rent houses from Vacation Home Rentals with wonderful views of the limestone outcropping, or “brac,” in the center of the island that gives Cayman Brac its name. Little Cayman is smaller and less developed than its sisters but is world famous for scuba-diving and has more than 50 unique dive sights. When it comes to vacation rentals, Cayman Islands have one to fit you, whether you’re looking for a quaint beach house or upscale condo.
Sightseeing in the Cayman Islands and Things to Do
  • Find Cayman Islands vacation rentals on Grand Cayman and enjoy the white sands and crystal waters of Seven Mile Beach, voted one of the world’s ultimate beaches.
  • Visit the imposing, three-story Pedro St. James Castle in Savannah.
  • Get up close with the local wildlife at Stingray City and interact year-round with the friendly southern stingray.
  • Scuba-dive and explore man-made reefs like the USS Kittiwake.
  • Learn about the maritime history of the Cayman Islands at East End Lighthouse Park on Grand Cayman.
  • Explore the history of the Cayman Islands at the National Museum.
  • Get away from it all and stay in one of our Cayman Islands rental homes on Little Cayman.
  • Visit the South Hole Sound Lagoon or dive at Bloody Bay Wall Marine Park.
  • Take the kids to Booby Pond Nature Reserve on Little Cayman and see red-footed boobies at the largest colony in the Western Hemisphere.
  • Enjoy Cayman Islands vacation rentals on Cayman Brac for their secluded beaches.
  • Bird-watch on Cayman Brac and catch a glimpse of the more than 200 species that call the island home.
  • Let loose your inner pirate during Pirates Week.
Regional Foods and Dining in the Cayman Islands
The cuisine of the Cayman Islands is a mix of Jamaican, British, and native culinary traditions often supplemented with international flair. Local dishes reflect the abundance of the islands and contain native fruits such as coconuts, plantains, breadfruit, and cassava. Seafood is prevalent in a variety of chowders and stews that contain conch, lobster, shrimp, and fresh fish. Browse our Cayman Islands condo rentals and step out on the town to enjoy international dining at any number of restaurants throughout the islands. For fishing enthusiasts, some restaurants have “you catch, we cook” options.
When to Visit the Cayman Islands
The Caymans enjoy a tropical marine climate. Temperatures hold steady around 80°F during the summer and hover near 70°F in winter. The summer is the wet season and lasts from May to October, with relatively dry, cool winters. The best time to visit the Cayman Islands and stay in offered rental properties is between May and June, when temperatures are at their best and the weather is calm and clear. Guests also book their Cayman Islands rentals around these festivals:
  • Mardi Gras (March)
  • Flower Sea Swim (June)
  • Constitution Day Fireworks (July)
  • Pirates Week (November)
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