Cayman Family Friendly Villa Collection

Cayman Family Friendly Villa Collection

We want to make your family villa vacation as comfortable as possible. Our villa specialists have handpicked properties that are particularly accommodating for families with young children. They can offer detailed insights into each property, including specifics about swimming pool depth, secure fencing, and other child-friendly features like playgrounds, kid’s clubs, and babysitting services. We can help you find the perfect family-friendly property for your vacation.

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
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
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
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
Sun Rays Villa in Cayman Kai
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
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
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
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
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
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'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
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
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 Bedrooms
7 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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