Cayman Villas & Vacation Rentals

These are the 72 most popular villa rentals in Cayman. Narrow your search above.

If you love the ocean, you'll love Villa Caymanas. It sits on Old Man's Bay, a quiet and undeveloped region known for amazing snorkeling. I love watching the waves roll ...
Villa Caymanas is located on the North side of the island on the beach
Available!
Grand Cayman, Cayman
  • Near Beach
  • Pool
  • AC
Details
Kailypso Villa is located in gorgeous Cayman Kai. Step out the back door onto the screened patio, or walk a little further to the private pool, boat dock, sandy beach, ...
Kailypso Villa is located in gorgeous Cayman Kai
Available!
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
Gypsy is perfect for a family who wants a beachfront vacation rental with spacious rooms, a private bay, and easy access to restaurants and activities. I love that there's two ...
Gypsy Villa in Rum Point
Available!
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
Envision is ideal for any family looking to unwind by the sea. This delightful beachfront villa is modern, with ample space inside and outdoors to relax. Guests may lounge by ...
Envision Villa is located beachfront on Cayman's North Side
Available!

Envision

5 Bedrooms
3+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
Fischer’s Reef is a great beachfront villa for large groups. There are four king suites, three queen suites, and a bunk room, so families can enjoy plenty of privacy ...
Fischer's Reef Villa is located in Rum Point right on the beach
Available!
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
This open-concept villa is perfect for families or groups who want space to spread out, an unbelievably convenient location, and easy access to the beach and sea. The villa is ...
S'Kai Blue Villa is located on Finger Cay
Available!

S'Kai Blue

4 Bedrooms
4+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
Details
Wind Upon The Waves Villa is offers seclusion, technology, and a modern vibe. Guests can sit back on the loungers and admire the oceanfront views, sip a cocktail by the ...
Win Upon the Waves Villa is located on the southern coast of Grand Cayman
Available!
Grand Cayman, Cayman
  • Pool
  • AC
Details
Hilltime is perfect for any family or couples who want to relax by the sea with minimal fuss. This villa is clean and simple, with plenty of space to relax ...
Hilltime Villa is located on the north coast of Cayman in Rum Point
Available!

Hilltime

5 Bedrooms
4 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
Nestled on a picturesque ridge with a stunning ocean view, Willow Beach in Cayman is the ultimate tropical paradise. This gem is complete with a pristine sandy beach, fantastic snorkeling, ...
Willow Beach in Cayman
Available!
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
If you want a private, oceanfront villa with a secluded beach, On The Rocks is a great choice. This villa would be great for a family vacation, because there's bedrooms ...
On the Rocks Villa is located in the Beach Bay community
Available!
Specials.
Grand Cayman, Cayman
  • Near Beach
  • Pool
  • AC
Details
Kai-Yak Cove is ideal for nature lovers! Guests can enjoy the bioluminescence tour from the comfort of their own dock, relax in the pool, or launch a kayak and enjoy ...
Patio and pool area
Available!
Grand Cayman, Cayman
  • Pool
  • AC
Details
Fantasea & Guest Cottage is the ultimate island getaway in Cayman. With a 2 bedroom main villa and a charming guest cottage, there's plenty of space for everyone. The pool and dock ...
Fantasea & Guest Cottage villa in Cayman
Available!
Cayman Kai, Cayman
  • Pool
  • AC
Details

Looking to rent a villa Cayman?

There are three islands in the Cayman Island chain-Grand Cayman, Little Cayman, and Cayman Brac. You will find vacation villas available on all three when you start looking for rental properties and accommodations. The Cayman Islands villas are spacious, private, and elegant. They are designed to accommodate larger groups of people traveling together, but offer visitors the option for private moments by setting up sleeping quarters as private suites. Most have en-suite bathrooms and private verandas off the bedrooms-but beware, a villa experience will spoil you.

What's special about Cayman?

Made up of three islands (Little Cayman, Cayman Brac, and Grand Cayman), the Cayman Islands are less than 500 miles off the Florida coast. A British held entity in the Caribbean Sea; the Cayman’s are a tourist’s delight. Grand Cayman, as the name implies, is the largest of the three islands, and the most populous. There are a variety of hotels, resorts, luxury villas, and guest houses available for rent on the islands.

Grand Cayman tends to be the most expensive of the three islands because there are more amenities for tourists to enjoy here. Its famous Seven Mile Beach is a huge draw for scuba diving, snorkeling, para-sailing, and sailing. The reefs and a wide variety of exotic fish and sea creatures make the waters around the island both a tourist’s and a photographer’s dream. If you’re looking for a five-star hotel on the beach, expect to pay top dollar for a room, but if you’re willing to travel a bit, you can find very comfortable and affordable guest houses and villas off the beaten path.

To occupy your days on the island-when you’re not on the beach or swimming in the Caribbean-there are shops aplenty ready to help you with your retail therapy. Many of the shops offer tax and duty free items so there are bargains to be found. If you want to grab a bite to eat, there are plenty of options for standard fare or ethnic cuisine. You can choose from Chinese, Italian, British, Middle Eastern, and Indian cuisine among others. And for those of you that just like your meat and potatoes, there are a number of steak houses to keep you happy.

Maybe you’re interested in the night life on the Cayman Islands rather than the shopping and dining. There are nightclubs everywhere, many offering live music and entertainment. You can grab a table on the sidewalk and enjoy the island breezes while you socialize, or head to the dance floor to work off some of those carbs you’ve been enjoying while you’re here. The Cayman’s are one of the top hot spots in the Caribbean, so you can be sure you’ll have a good time.