Grand Cayman, Cayman Villas & Vacation Rentals

These are the 71 most popular villa rentals in Grand Cayman, Cayman. Narrow your search above.

This luxury villa is absolutely beautiful and has plenty of room for any group. The outdoor space is amazing, with water sports equipment, an outdoor kitchen, and beach access. There’...
The pool and beautiful beach at Kaia Kamina
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
Paradis Sur Mer is an inarguably beautiful villa, but the real advantage is its beachfront location. The beach has sugar soft sand, barefoot entry into shallow water, and a sandbar 100 ...
Paradis Sur Mer is located on a quiet residential road in Cayman Kai
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
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
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
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
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
Grand Cayman, Cayman
  • Pool
  • AC
If you're looking for luxury, Kempa Caribe is the place to be. Not only is this villa on a massive beachfront estate, it's also decked out with five-star amenities for ...
Castillo Caribe is located on the southern coast of Grand Cayman
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

Looking to rent a villa Grand Cayman, 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 Grand Cayman, 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.