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Cayman Villas & Vacation Rentals

These are the 73 most popular villa rentals in Cayman. Narrow your search above.

This villa has an amazing private beach that's perfectly set up for parties and al fresco feasts. The bedrooms are spread out throughout the two levels, which gives everyone plenty ...
Kai Zen is located in the private Cayman Kai resort neighborhood within Rum Point

Kai Zen

3 3+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Rip Kai is a magnificent, oceanfront estate perfect for your next Grand Cayman vacation. It's prepared to handle families celebrating milestone events with luxury and privacy, or your next unforgettable ...
Rip Kai Villa in Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
If you want your own private beachfront home with plenty of room for all 20 of your guests, Seascape is for you. A large wall of windows on every floor allows ...
Seascape is located on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Perched on the coast, Sun Salutations Villa has spacious, modern interiors and stunning views that make it an ideal spot for your next vacation getaway. This villa's large Great Room ...
The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Turtle Beach has one feature that you'd be hard-pressed to find at most other villas - swimming with sea turtles! The water is clear, shallow, and offers barefront entry in ...
Turtle Beach Villa is located on the oceanfront in Spotts

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed for fun and relaxation. The beach is steps away, and ...
Kempa Kai villa is located on a nature preserve near Rum Point

Kempa Kai

7 7

Grand Cayman, Cayman

Beachfront | AC

Details
Lone Palm gives guests an up close and personal view of the ocean. In fact, the sea is a few steps away! Jump into waves that are all your own, ...
Lone Palm Villa is located on a beautiful white sand beach
Specials.

Lone Palm

3 3

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, from the kitchen gadgets to the complimentary cribs to the ...
Seafire Resort

Grand Cayman, Cayman

Beachfront | AC

Details
From the inviting front exterior to the contemporary furnishings, from the large pool to the quiet beach, Kaiku Villa is deluxe in every way. It has the feel of a ...
Kaiku Villa is located in Rum Point on the ocean with its own beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
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

Details
This villa has a great open floor plan and sits on picturesque Cayman Kai. The high ceilings, minimal design, and walls of glass windows bring the sea in, and the ...
Ocean Kai sits directly on the beach near Rum Point

Ocean Kai

6 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Babylon Reef feels like a classic beach house, with every amenity you could ask for. It's oceanfront, with a great view of the Caribbean framed by palm fronds. A hammock ...
The private pool at Babylon Reef has a man made -beach- surrounding it

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This rental property combines two villas into a supersized vacation home. Casa Luna is great for travelers who want the privacy of a villa without losing resort amenities and vacationers ...
Casa Luna

Casa Luna

6 6+

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
Point of View is a great villa rental for large groups of travelers who want to be near the beach without sacrificing comfort. There's too many notable features to list, ...
Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This is a fantastic property for large families or groups that are working within a budget. There is plenty of space in this six/seven bedroom home for all to ...
Twin Palms is located near Rum Point on a beautiful stretch of ocean

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, and a guest cottage with kitchenette. The pool terrace is ...
Cayman Sands is located in Old Man Bay along a beautiful stretch of white sandy beach
Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Casa Luna 16 has next-level benefits for anyone seeking privacy, resort amenities, and luxury. The exterior is tricked out for entertaining and dining, and the resort's pool and barefoot beach are ...
Casa Luna 16 is located in the exclusive resort at the very end of Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
Clear aquamarine water packed with beautiful marine animals. A secluded beach with calm water just waiting for you. It is not just your Monday morning fantasy. It is a reality ...
Aerial view of Coral Kai Villa on Rum Point Grand Cayman
Specials.

Coral Kai

5 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
If you love the sea, Cayman Castle and Guesthouse is the place to be. This expansive villa enjoys an oceanfront location on Gun Bay near snorkeling reefs, the Wreck of ...
Cayman Castle is located on incredible beach frontage on Gun Bay

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
Villa Mora balances luxury, access, and spaciousness. With 8,000 square feet and beachfront access, everyone in your party will have plenty of room to spread out and relax. In addition to ...
Villa Mora is located beachfront in South Sound

Villa Mora

7 7+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
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

Details
Finding the perfect mix of oceanfront and privacy for a larger family can be difficult at times, but Coconut Villa makes it easier. The villa's freshwater pool, al fresco dining ...
Coconut Beach villa is right on the Beach near Rum Point
Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, between the guest cottage and three bedrooms on opposite sides ...
Great Escape Villa is located on the Rum Point end of the island with a beautiful stretch of beach
Specials.

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
Our Cayman Cottage is pretty impressive. This villa was made for family reunions, with ample space for kids and adults to spread out and let loose. I love how the ...
Our Cayman Cottage sits along a beautiful stretch of beach on the north side of Grand Cayman
Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
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

Details
Abita Kai is a great choice for a multi-generational family vacation. With three bedrooms spread across two levels of the main house and two bedrooms in the guest cottage, there's ...
Abita Kai is located on a beautiful stretch of white sand beach in Cayman Kai

Abita Kai

5 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms that have their own ensuite bathrooms and then a huge ...
Reef Romance Villa has an ideal oceanfront location on Rum Point
Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This two-story villa has great sunsets over the water, and is near popular Rum Point. There’s floor to ceiling windows throughout the rental that face the ocean view, so ...
Cos Kai is located on a beautiful beach near Rum Point
Specials.

Cos Kai

5 4+

Grand Cayman, Cayman

Beachfront | AC

Details
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

Details
Sun Rays Villa in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Coconut Walk is a gorgeous choice for a group vacation. The villa is modern, elegant, and well-designed for large parties. Most of the bedrooms are on the upper level, but ...
Coconut Walk is an oceanfront estate on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Blue Serenity is perfect for quiet, relaxing vacations away from everyday activity. Give yourself a break from non stop hustle, and just relax by the pool or take a swim ...
Blue Serenity Villa is located along the central south coast of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
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

Details
Bella Rocca in Cayman is the epitome of luxury. Perfect for large groups, it's even ideal for weddings. But what I really love about this villa is the sheer beauty ...
Bella Rocca villa in Cayman

Grand Cayman, Cayman

Pool | AC

Details
White Cottage is a great vacation rental for anyone who loves the ocean and privacy. It's in a quiet region of Grand Cayman, and sits steps away from the beach. ...
White Cottage is a great beachfront villa

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Casa Luna 17 is great for families who want a bit of privacy at a great price. Kids can stay on the lower level in two suites, and the basement-level bathroom ...
There is an amazing beach cove at Casa Luna Villas

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
Peace Bay House is perfect for several families or a group with its ample square footage and many amenities to indulge in. An infinity pool and large deck that overlooks ...
Pease Bay House in Cayman

Grand Cayman, Cayman

Beachfront | Pool | 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

Grand Cayman, Cayman

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

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Evolution is going to revolutionize your next family vacation. Not only is there a specific children's bedroom, but there's also games and activities throughout the house that kids will love. ...
Evolution Vill offers it all - right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Escape to paradise at We'll Sea in Cayman! This two-bedroom beachfront villa is situated in Cayman Kai, close to the popular Rum Point Club. Make the most of your getaway ...
Terrace views of the beach

We'll Sea

2 2+

Grand Cayman, Cayman

Beachfront | AC

Details
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

Details
If you want a beachfront villa with private bedrooms, a generous lap pool, and amazing snorkeling, Mora is a great choice. There are seven bedrooms spread between the two-story main ...
Villa Mora is located on a beautiful beachfront in South Sound

Mora

7 7

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Just For Fun has amenities for any traveler and is well-designed for families and friends alike. The bioluminescent bay, tennis courts, and Rum Point beach are all a few minutes ...
Amazing waterfront pool at Just for fun Villa
Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
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

Details
If you're looking for a place to kick back and relax, you won't find anywhere better than Hidden Treasure in Cayman! With 5 bedrooms, a beachfront location, and 100 feet of sandy ...
 Hidden Treasure Villa is centrally located on the southern coast

Grand Cayman, Cayman

Beachfront | 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

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
White Dahlia is a gorgeous couples' getaway villa. It has four king suites, but the fourth suite can be made up with two twins if you're bringing kids along. The ...
White Dahlia is located right on Bioluminescent Bay

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
This spacious, beachfront villa has a convenient location within walking distance of dining, attractions, and excursions. Even though Rum Point Beach and Cayman Kai are minutes away, Les Jalousies has ...
Les Jalousies is located in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Many people like to stay on Seven Mile beach because that's where all the action is. Then there are others who still want to experience the beauty of Grand Cayman ...
View from above Castaway Villa - you can see the beach and the ocean

Grand Cayman, Cayman

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

Envision

5 3+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
I think this villa would be perfect for a family vacation-- it has three master bedrooms upstairs and a twin bedroom downstairs, and each bedroom is really well-sized. The views ...
A beachfront pool awaits you at Christmas Palms Villa
Specials.

Grand Cayman, Cayman

Pool | AC

Details
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

Details
This house is great for two families to share. There are two king suites that each have exterior access, and two queen suites with no exterior access. Plus, the villa ...
Heritage House Villa is located on the very desirable Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Hidden Cove is perfect if you love being on the water and want a bit of privacy. It's near great snorkeling reefs, the bioluminescent bay, and Rum Point Beach, so ...
Hidden Cove is located in Cayman Kai neighborhood
Specials.

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, residential East End. The beach is practically deserted, and there's ...
Great Bluff Estates sits along the beautiful northern coast of Grand cayman
Specials.

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
Specials.

Grand Cayman, Cayman

Near Beach | 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

Hilltime

5 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
If you want ultimate privacy and seclusion, this villa is for you. Far away from the hustle of Seven Mile Beach, this location can be a long drive to Georgetown. ...
Fingertip villa is located beachfront in exclusive Cayman Kai

Grand Cayman, Cayman

Beachfront | AC

Details
This gorgeous villa is perfect if you want to be near Seven Mile Beach, but away from the crowds. There’s tons to do at and around the villa, so ...
Casa Luna 4 is located in the resort community along the coastline just south of Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
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Looking to rent a villa in 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.

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