Cayman Islands Vacation Rentals

29 Rentals

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3BR / 2BA - Sleeps 8 - Seven Mile Beach Condo

Our condo has 3 spacious bedrooms , accommodating 6 to 8 people , with magnificent views of the ocean...

$250 - $575 / nt

1 Review

1BR / 1BA - Sleeps 3 - North East Bay Cottage

Featherstone's House of the Rising Sun is a new two story guest cottage. Professionally decorated and...

$136 / nt

East End Cayman Islands Vacation Rentals - Condo

1BR / 1BA - Sleeps 4 - East End Condo

One Bedroom Oceanfront Condominium, 1 Bath, Sleeps 4 Morritt's Tortuga Club offers you a beachfront...

$172 / nt

Beautiful Little Cayman

3BR / 3BA - Sleeps 6 - Little Cayman Condo

When Only The Best Will Do! Nestled On Secluded South Hole Sound, The Club At Little Cayman Is The...

$400 - $550 / nt

1 Review
7 Mile Beach - Chairs & Umbrella provided

2BR / 2BA - Sleeps 6 - Seven Mile Beach Condo

Ideally located condo on the renowned 7 mile beach. This spacious condo, on the 3rd floor, has 2 bedrooms,...

$155 - $275 / nt

3BR / 2BA - Sleeps 9 - Seven Mile Beach Condo

Modern and tastefully decorated spacious 3 bed 2. 5 bath condo centrally located off seven mile beach....

$295 - $525 / nt

2BR / 2BA - Sleeps 4 - Seven Mile Beach Villa

Located on the beautiful Seven Mile Beach, South Bay Beach Club luxury condominium offers a fully equipped...

3BR / 2BA - Sleeps 7 - Seven Mile Beach Apartment

One of the few 3 bedroom condos on Seven Mile Beach that sleep up 7 people including a huge top floor...

$458 - $608 / nt

1BR / 1BA - Sleeps 4 - Seven Mile Beach Apartment

Nestled on a quiet beach on north west point is an attractive Spanish style resort called Villas Pappagallo....

$198 - $284 / nt

2BR / 2BA - Sleeps 5 - Seven Mile Beach Apartment

Prime location right on the water's edge! This recently renovated 2 bed/2bath condo with top of the...

$309 - $458 / nt

Little Cayman Cayman Islands Vacation Rentals - Villa

4BR / 3BA - Sleeps 10 - Little Cayman Villa

This spacious nautical style duplex villa is situated in a quiet setting and yet within easy walking...

$710 - $1,018 / nt

4BR / 5BA - Sleeps 10 - Seven Mile Beach Apartment

Luxury Design and Front- Row Sunset Views on Seven Mile BeachA stunning sunset show awaits you at Seabreeze...

$923 - $1,420 / nt

East End Cayman Islands Vacation Rentals - Villa

3BR / 2BA - Sleeps 8 - East End Villa

This spacious and secluded 3 bedroom plus den (with queen sleeper sofa) villa is nestled on top of a...

$538 - $611 / nt

3BR / 3BA - Sleeps 8 - Little Cayman Apartment

Walk directly from your classic beach cottage to the palm- shaded beach in one- of- a- kind Little Cayman,...

$473 - $545 / nt

2BR / 2BA - Sleeps 4 - Seven Mile Beach Apartment

As the name suggests, this convenient condo resort is near to the main town of George Town, as well...

$285 - $452 / nt

Cayman Kai Cayman Islands Vacation Rentals - Apartment

3BR / 3BA - Sleeps 6 - Cayman Kai Apartment

Experience the delight and tranquility of this charming free standing villa in a small but expansive...

$454 - $646 / nt

Cayman Kai Cayman Islands Vacation Rentals - Home

1BR / 1BA - Sleeps 4 - Cayman Kai Home

These cozy side- by- side apartments are situated in a peaceful little sandy cove right across from famous...

$213 - $284 / nt

George Town Cayman Islands Vacation Rentals - Home

4BR / 4BA - Sleeps 10 - George Town Home

For active travellers, Boa Vida is heaven on earth. At this property in the Seven Mile beach area—which...

$994 - $1,420 / nt

2BR / 2BA - Sleeps 6 - Little Cayman Villa

Walk directly from your classic beach cottage to the palm- shaded beach in one- of- a- kind Little Cayman,...

$400 - $458 / nt

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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