Cayman Family Villas

Cayman Family Villas


The Caribbean is a great destination choice for families or multiple families traveling together. With a private kitchen and enough space for everyone, a Caribbean villa rental can be the most economical accommodation choice. Whether you are seeking a beachfront villa, a private island or a hillside villa with an amazing view, our favorite family villas section provides some of the best villas in the Caribbean for your family vacation.


Coconut Walk was designed to maximize views and luxury. You can see the ocean from almost everywhere in the house, ... Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4450/Nt
Villa Del Mare is the ideal oceanfront villa. It's near Rum Point, which is one of Grand Cayman's most elegant ... Villa Del Mare is in an ideal oceanfront location near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2950/Nt
If you're looking for luxury, Castillo Caribe is the place to be. Not only is this villa on a massive ... Castillo Caribe is located on the southern coast of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $15000/Nt
Coconut Walk is a gorgeous choice for a group vacation. The villa is modern, elegant, and well-designed for large parties. ... Coconut Walk is an oceanfront estate on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4450/Nt
Villa Del Mare has plenty of space for your next large group vacation. Whether you’re bringing your family, friends, ... Villa Del Mare is located on Rum Point Drive and has a great beach area

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2950/Nt
Fischer’s Reef is a great beachfront villa for large groups. There are four king suites, three queen suites, and ... Fischer's Reef Villa is located in Rum Point right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2950/Nt
Kaiku is a fun choice for your next luxury beachfront vacation. The house sits right on the beach and has ... 7 BR rate available. Kaiku is located on the Rum Point end of the island directly on Bio-luminescent Bay

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1850/Nt
From the inviting front exterior to the contemporary furnishings, from the large pool to the quiet beach, Kaiku Villa is ... 7 BR rate available.
Has specials.
Kaiku is located on the Rum Point end of the island directly on Bio-luminescent Bay

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1850/Nt
You'll never lack entertainment here at Fischer's Reef. Have a cornhole tournament by the pool, read in the gazebo, or ... Has specials. Fischer's Reef Villa is located right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2950/Nt
Our Cayman Cottage is pretty impressive. This villa was made for family reunions, with ample space for kids and adults ... Has specials. Our Cayman Cottage sits along a beautiful stretch of  beach on the north side of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1195/Nt
Evolution is going to revolutionize your next family vacation. Not only is there a specific children's bedroom, but there's also ... Has specials. Evolution Vill offers it all - right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Tatenda is a great family villa because its far enough from cruise traffic and tourist spots to actually relax, but ... Has specials. Tatenda Villa is a beautiful beach front home just along South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
This luxury villa is absolutely beautiful and has plenty of room for any group. The outdoor space is amazing, with ... Has specials. The pool and beautiful beach at Kaia Kamina

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
If you love the sea, Cayman Castle and Guesthouse is the place to be. This expansive villa enjoys an oceanfront ... Cayman Castle and Guesthouse are located on Gun Bay in Grand Cayman

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
Twin Palms really stands out, and not just for its unique ocean view. The beach is silky soft, has great ... Twin Palms is located near Rum Point on a beautiful stretch of ocean

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
If you want a beachfront villa with private bedrooms, a generous lap pool, and amazing snorkeling, Mora is a great ... Villa Mora is located on a beautiful beachfront in South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1650/Nt
Our Cayman Cottage is a massive, oceanfront escape perfect for your next Grand Cayman vacation. It’s secluded on the ... Our Cayman cottage is located on the island's East End

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1195/Nt
This is a fantastic property for large families or groups that are working within a budget. There is plenty of ... Has specials. Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
Villa Mora balances luxury, access, and spaciousness. With 8,000 square feet and beachfront access, everyone in your party will have plenty ... Has specials. Villa Mora is located beachfront in South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1650/Nt
Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take ... Has specials. Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
If you want your own private beachfront home with plenty of room for all 17 of your guests, Seascape is for ... Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

from $3000/Nt
If you want a private, oceanfront villa with a secluded beach, On The Rocks is a great choice. This villa ... Has specials. On the Rocks Villa is located in the Beach Bay community

Grand Cayman, Cayman

Near Beach | Pool

from $950/Nt
Oceanus is the perfect place to host your next family reunion, corporate retreat, or special event. This villa rental is ... Has specials. Beachfront pool at Oceanus Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed ... Kempa Kai villa is located on a nature preserve near Rum Point

Grand Cayman, Cayman

Beachfront | AC

from $2395/Nt
If you’re looking for all the comforts of home with a gorgeous tropical setting, Amarone is the place to ... Amarone Villa is located on South Sound Road with a beautiful stretch of white sand beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1300/Nt
Moon Kai is a great family vacation villa on a barefoot beach in Cayman Kai. The villa is designed for ... Moon Kai is located right on a white sandy beach with in walking distance to Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
Calypso Blue feels like home as soon as you approach the circle drive. With 4 bedrooms and 3.5 bathrooms, a family or 2 ... Has specials. Enjoy endless views of the ocean from Calypso Blue Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $650/Nt
Perched on the coast, Sun Salutations Villa has spacious, modern interiors and stunning views that make it an ideal spot ... Has specials. The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2499/Nt
Finding the perfect mix of oceanfront and privacy for a larger family can be difficult at times, but Coconut Villa ... Has specials. Coconut Beach villa is right on the Beach near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
Facing the impressive coast of the Caribbean Sea in Rum Point, Moon Kai Villa has six bedrooms that provide you ... Has specials. Moon Kai has a beachfront pool where you can lounge in the Caribbean sun

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
Tranquility Cove lives up to its name. This beachfront villa sits mere feet from the South Sound, with plenty of ... Has specials. Tranquility Cove Villa has a luxurious infinity edge pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Hidden Cove is perfect if you love being on the water and want a bit of privacy. It's near great ... Has specials. An aerial view of Hidden Cove Villa - it is located just adjacent to the Bio-luminescent Bay

Grand Cayman, Cayman

Near Beach | Pool

from $600/Nt
The best thing about this villa is easily the location. It's right on South Sound Beach, which is calm and ... Has specials. Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1300/Nt
Point of View is a great villa rental for large groups of travelers who want to be near the beach ... Has specials. Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
Crystal Waters, formerly known as Mudslide, is the perfect villa for your next family vacation. Every room is oversized, and ... Has specials. Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
Hilltime is perfect for any family or couples who want to relax by the sea with minimal fuss. This villa ... Has specials. Hilltime Villa is located on the north coast of Cayman in Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $695/Nt
White Cottage is a great vacation rental for anyone who loves the ocean and privacy. It's in a quiet region ... Has specials. White Cottage is a great beachfront villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, ... Has specials. Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $995/Nt
Nirvana's bohemian design adds a homey touch to the five star amenities, and having your own private beach is the ... Has specials. Nirvana photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1469/Nt
Abita Kai is a great choice for a multi-generational family vacation. With three bedrooms spread across two levels of the ... Has specials. Abita Kai is located on a beautiful stretch of white sand beach in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
Looking for luxury? Crystal Waters has it in spades. This beachfront villa has an ideal location within walking distance of ... Has specials. Crystal Waters Villa is located just across the street from the Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
If you’re traveling with a large group, Ocean Kai is a great villa! It’s spacious, the bedrooms are ... Ocean Kai Villa is located in Cayman Kai near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $925/Nt
Blue Water is the place to be for large groups. There are five bedrooms that can all accommodate couples, although ... Blue Water Villa is located on Rum Point Drive on a beautiful stretch of white sand beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
Great Bluff Estates is a fun, gorgeous place to be on Grand Cayman’s beachfront. There are several levels to ... Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $995/Nt
Pease Bay House is a luxurious, gorgeous villa that’s totally equipped for your next beachfront vacation. A large part ... Pease Bay House sits along a secluded sandy beach in Bodden Town

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1495/Nt
Two Rainbows is a fantastic choice for your next family vacation if you want total relaxation. This villa is on ... Has specials. Two Rainbows is located within walking distance to the Rum Point Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
Peace Bay House is perfect for several families or a group with its ample square footage and many amenities to ... Has specials. Lounge poolside on the beach at Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1495/Nt
Clear aquamarine water packed with beautiful marine animals. A secluded beach with calm water just waiting for you. It is ... Has specials. Aerial view of Coral Kai Villa on Rum Point Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, ... Has specials. Cayman Sands is located in Old Man Bay along a beautiful stretch of white sandy beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
What is there not to love about Kai Conut Villa. This ocean front property is open and airy with five ... Has specials. The pool at Kai Conut is just steps away from the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms ... Has specials. The pool and this cabana are located right on the beach at Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
Blue Water Villa is an impressive gated property perfect for your next family vacation. As you drive through the gates, ... Has specials. Blue Water is located on Rum Point with a beautiful stretch of beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
This villa has a great open floor plan and sits on picturesque Cayman Kai. The high ceilings, minimal design, and ... Has specials. Ocean Kai sits directly on the beach near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $925/Nt
This beachfront villa in Rum Point has tons of outdoor activities, from volleyball to snorkeling to swimming. For air-conditioned activities, ... Has specials. Sea Grape Villa sits just on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $525/Nt
The Residences at Seafire 5 Bedroom is a beachfront resort villa with luxurious amenities, an ideal location, and modern interiors. Guests ... The Residences at Seafire are located directly on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $2500/Nt
Stepping Stone has unreal ocean views and a perfect, private stretch of beach. It's pretty secluded, on a quiet end ... Has specials. Stepping Stone Villa is located along a beautiful beach at the East End of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1769/Nt
Olympus is a modern, beachfront villa with full air-conditioning and an enviable location near Rum Point Beach. Rum Point is ... Has specials. An aerial view of Olympus Villa and the beautiful beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
Gypsy is the place to be for a relaxing beachfront vacation. It’s right by the water in Rum Point, ... Gypsy is located in Rum Point right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $725/Nt
Kai Vista is a charming beachfront villa for couples or families with older kids. It’s a short walk to ... Kai Vista is located in Rum Point along the north coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax ... Olympus is located on the beach front in Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
Tarasand Villa is a great choice for anyone who wants to be near Rum Point and have easy access to ... Tarasand sits on the waterfront in Cayman Kai, a short distance from Rum Point

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, ... Has specials. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Near Beach | Pool

from $645/Nt
Many people like to stay on Seven Mile beach because that's where all the action is. Then there are others ... Has specials. View from above Castaway Villa - you can see the beach and the ocean

Grand Cayman, Cayman

from $415/Nt
Kai Vista is a colorful oceanfront villa that encompasses all that an idyllic, tropical getaway destination should. After long evening ... Has specials. Kai Vista photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
In Harmony is a charming beachfront villa that would be perfect for your next family vacation. It has a private ... Has specials. An aerial view of in Harmony Villa located directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $770/Nt
If you love the ocean, you'll love vacationing at Serenity Now. The villa is a minute from Seven Mile Beach, ... Has specials. Serenity Now Villa is located in the West Bay area and is steps away from Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
I think this villa would be perfect for a family vacation-- it has three master bedrooms upstairs and a twin ... Has specials. A beachfront pool awaits you at Christmas Palms Villa

Grand Cayman, Cayman

Pool

from $525/Nt
Tarasand villa is a great choice for anyone who wants to be near Rum Point and have easy access to ... Has specials. The beach set up in front of Tarasand Villa

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
If you love the ocean, you'll love Villa Caymanas. It sits on Old Man's Bay, a quiet and undeveloped region ... Has specials. Villa Caymanas is located on the North side of the island on the beach

Grand Cayman, Cayman

Near Beach | Pool

from $525/Nt
Picture Perfect has a great location for travelers who want to be near Seven Mile Beach and George Town. Snorkeling ... Has specials. Picture Perfect Villa has many options for a fun holiday

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
This house is great for two families to share. There are two king suites that each have exterior access, and ... Has specials. Heritage House Villa is located on the very desirable Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $525/Nt
Gypsy is perfect for a family who wants a beachfront vacation rental with spacious rooms, a private bay, and easy ... Has specials. Gypsy Villa has a beautiful beach front private pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $725/Nt
The four bedroom residence at Seafire Resort is a great choice for a large family. Two queen suites, the master, ... The Residences at Seafire are located directly on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $2000/Nt
Babylon Reef feels like a classic beach house, with every amenity you could ask for. It's oceanfront, with a great ... Has specials. The private pool at Babylon Reef has a man made -beach- surrounding it

Grand Cayman, Cayman

Beachfront | Pool | AC

from $495/Nt
Infinite Horizon is a gorgeous family vacation villa. It has WiFi, SONOS, a media room, a pool, and the beach ... Has specials. Infinite Horizon Villa is located on the beach just minutes from Seven Mile Beach Corridor

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
This spacious, beachfront villa has a convenient location within walking distance of dining, attractions, and excursions. Even though Rum Point ... Has specials. Les Jalousies is located in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1207/Nt
This resort villa is the perfect choice if you want a convenient, blissful family vacation on Seven Mile Beach. You ... The Residences at Seafire are located on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $1500/Nt
This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, ... Seafire Resort

Grand Cayman, Cayman

Beachfront | AC

from $1500/Nt
This gorgeous villa is perfect if you want to be near Seven Mile Beach, but away from the crowds. There’... Has specials. Casa Luna 4 is located in the resort community along the coastline just south of Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $750/Nt

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