Cayman Villas & Vacation Rentals

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

Sea 2 Infinity is the perfect villa for your next holiday. The villa is right on the beach and features stand-up paddle boards, a private pool, and a white sandy beach ...
Sea 2 Infinity Villa is located right on the beach in Cayman Kai
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Tarasand villa is a great choice for anyone who wants to be near Rum Point and have easy access to snorkeling, water sports, and the beach. The lower level has ...
The beach set up in front of Tarasand Villa
Grand Cayman, Cayman
  • Beachfront
  • AC
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
Grand Cayman, Cayman
  • Near Beach
  • Pool
  • AC
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
Grand Cayman, Cayman
  • Pool
  • AC
Indulge in island paradise at Wight Away in Cayman Kai. This 4-bedroom villa boasts a boat dock and wrap-around porch with a pool, just a stone's throw from Rum Point ...
Wight Away in Cayman Kai

Wight Away

4 Bedrooms
3+ Bathrooms
Cayman Kai, Cayman
  • Pool
  • AC
Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax inside or out, there’s plenty of space for all ...
Olympus is located on the beach front in Rum Point
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Imagine yourself in the lap of luxury at Ritz-Carlton Deckhouse #1 - Platinum in Cayman. This stunning Balinese waterfront villa boasts a private swimming pool, exquisite decor, and sweeping views of ...
Ritz-Carlton Deckhouse #1 in Seven Mile Beach
Grand Cayman, Cayman
  • Pool
  • AC
  • Resort Villa
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
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
What is there not to love about Kai Conut Villa. This ocean front property is open and airy with five bedrooms and offers great amenities to help you relax. You ...
The pool at Kai Conut is just steps away from the beach
Specials.
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
This is a five bedroom home known by guests as the perfect find for those who want a private vacation destination. This villa is set on a gorgeous, quiet piece ...
Two Rainbows is located in the Rum Point area of Grand Cayman
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Moon Kai is a great family vacation villa on a barefoot beach in Cayman Kai. The villa is designed for comfort, from the soft sand and calm water to the ...
Moon Kai - Platinum photo
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC

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.