Grand Cayman, Cayman Villas & Vacation Rentals

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

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 in Rum Point

Ocean Kai

6 Bedrooms
5 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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 Bedrooms
7 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
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
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 Bedrooms
7+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
At Iggy Blue, you can take a dip in the pool with a stunning sea view, relax in the hot tub under the screened porch, and explore the beautiful beachfront ...
Iggy Blue Villa in Rum Point

Iggy Blue

4 Bedrooms
5 Bathrooms
Rum Point, Cayman
  • Beachfront
  • Pool
  • AC
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
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 Bedrooms
6+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
  • Resort Villa
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
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
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
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
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
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 Bedrooms
4+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
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 Bedrooms
3 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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

S'Kai Blue

4 Bedrooms
4+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
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 Bedrooms
3+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take in the view, and is close to some of the ...
Cayman Castle is located on incredible beach frontage on Gun Bay
Grand Cayman, Cayman
  • Near Beach
  • Pool
  • AC
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 ...
Coral Kai on Rum Point
Specials.

Coral Kai

5 Bedrooms
5 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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 Bedrooms
5 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
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 Bedrooms
4 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • 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
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
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
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
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
Indulge in the ultimate beachfront escape at the luxurious Timeless Paradise Villa. With breathtaking views, an infinity pool, and 11 bedrooms, this one-of-a-kind property is perfect for large groups and families. ...
Timeless Paradise Villa in Rum Point
Rum Point, Cayman
  • Beachfront
  • Pool
  • AC
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
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
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
Specials.
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
In Harmony is a charming beachfront villa that would be perfect for your next family vacation. It has a private beach just beyond the deck with a rocky shoreline that ...
An aerial view of in Harmony Villa located directly on the beach
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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 Bedrooms
3+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
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
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
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
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
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 Bedrooms
2+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
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
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
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
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
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
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
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
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
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
Sea Orchard Retreat is a great choice for weddings, groups, or family vacations. Located a short drive from Seven Mile Beach, and a short walk from Barkers Beach, guests will ...
Sea Orchard Retreat is a gated oceanfront boutique of cottages on the northern coast of Grand Cayman
Grand Cayman, Cayman
  • AC
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
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
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
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
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
Sun Rays Villa in Cayman Kai
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
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
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
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
Cayman Kai, Cayman
  • 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

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.