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Kailypso
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Cayman Kai 3 2 8 $395 4,788 Inquire
Kailypso Cayman Kai Grand Cayman

Friends and families love this 3-bedroom, 2-bath beach house tucked into a private cove in a residential area in Cayman Kai, strolling distance from Rum Point.

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Shellen
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
East End 3 2 8 $270 4,234 Inquire
Shellen Villa Prospect Point Grand Cayman

Tuck into your own private mini-resort at Shellen, a 3-bedroom (plus sleeper sofa), 2-bath villa poised at the edge of the rocky, dramatic Caribbean coastline.

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Sir Turtle Villa
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Little Cayman 4 2 10 $360 $6,965 $9,450
Sir Turtle Villa Little Cayman

Sir Turtle Beach Villa defines Caribbean paradise. It sits on an exceptional stretch of private beachfront on the small and quiet island paradise of Little Cayman, with soft white sand to sink your feet into, an endless stretch of azure water to swim, kayak and snorkel, and tilted palms to shade your beachfront nap

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Serenity Now
Location Beds Baths Sleeps Nightly Low Nightly High Weekly Peak
West Bay 4 3 10 $990 $6,965 $9,450
Serenity Now Cayman

We jumped at the chance to offer guests their own villa on the north end of Seven Mile Beach – a rare luxury at this world-famous destination – and made an offer on this Caribbean charmer on the spot

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KV Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Rum Point 4 3 10 $5,460 $6,965 $9,450
Sir Turtle Beach I Little Cayman

Luxury "KV Villa" is directly oceanfront in Rum Point on the north coast. This lovely villa sits elevated on a ridge and offers excellent snorkeling directly behind the oceanfront infinity pool and hot tub. Only 250 yards from the Rum Point Club, KV Villa couldn't have a better location. A very sandy beach offers long walks in either direction. Pool shoes/fins required for swimming or snorkeling anywhere there is a marine environment.

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Boa Vida
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Seven Mile Beach 4 3.5 12 $610 Inquire Inquire
Boa Vida Cayman

At this property in the Seven Mile beach area—which sleeps 12 in 4 bedrooms and sofa bed in the den—two kayaks wait for you to discover the gorgeous, swimmable waterways just outside. Or rent a boat and launch an exploratory trip from your private, fenced boat dock.

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In Harmony
Location Beds Baths Sleeps Nightly Low Nightly High Weekly Peak
Bodden Town 4 4 8 $1,045 6,300 Inquire
In Harmony Cayman Kai Grand Cayman

Escape the stress of your daily life, but keep the comforts of your home. In Harmony Villa is our most down-to-earth option, with bright, sea-view spaces where families can gather and private nooks for tucking away with a new novel

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Pelican Point
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Grand Cayman 4 4 8 4,788 6,300 Inquire
Pelican Point Cayman Kai Grand Cayman

This 4 bed, 4 bath beach front villa is situated on a sandy beach on the northern shore about a 40 minute drive from George Town and the airport, but only minutes away from a restaurants, beach bars, a water-sports shop and a small grocery store. Almost all rooms have a magnificent view of the natural form pool with slide, sandy beach and warm Caribbean sea.

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Blue Lagoon
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Grand Cayman 4 4.5 8 $4,840 Inquire Inquire
Blue Lagoon Cayman Kai Grand Cayman

This charming 4 bed, 4.5 bath Caymanian style home is situated on a quiet, peaceful inlet of calm water. It is within walking distance of a beach-bar, restaurant and water-sports shop. A few other restaurants, bars and grocery store within a 15 minutes drive.

 

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Villa La Playa
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Cayman Kai 4 4.5 9 $430 Inquire Inquire
Villa La Playa Grand Cayman

This authentic Caymanian gem in the quiet residential neighbourhood of Cayman Kai will charm you with its waterfront location, swimming pool, traditional island architecture, distinctive paint colours, and surprisingly spacious interior with 4 bedrooms, 4.5 baths and an open-concept floor plan. All situated on a tranquil inlet on Grand Cayman’s northern shore

 

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Sea Breeze 8
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Grand Cayman 4 4.5 8 $1,032 Inquire Inquire
Sea Breeze 8 Cayman Kai Grand Cayman

A stunning sunset show awaits you at Seabreeze 8. This 4-bedroom, 4.5-bath, 4th floor unit provides a coveted vantage point for that perfect minute when the sun slides into the Caribbean—and many other unforgettable moments, too

 

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Sea Spray
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Grand Cayman 4 5.5 11 $668 Inquire Inquire
Sea Spray Cayman Kai Grand Cayman

An illuminated, overflow swimming pool suspended above the rippling blue blanket of the Caribbean Sea is just the icing on the cake at 3-bedroom, 3-bath Sea Spray on Grand Cayman’s East End. Perched atop Beach Bay Ridge, Sea Spray is a beautiful, windswept villa with all-encompassing ocean views and unmatched coastal luxury inside and out

 

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Nirvana
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
South Side 5 4 10 $1,320 Inquire Inquire
Nirvana Cayman Kai

Paradise is all around you at Nirvana, a five-bedroom, four-bath villa just a ten-minute drive from Seven Mile Beach. Featuring floor-to-ceiling views of the sea, contemporary architecture, and zen-inspired art and furnishings, Nirvana will be your family’s vacation happy place

 

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Awakening
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
North Side 5 4.5 10 $1,608 Inquire Inquire
Awakening Cayman Kai

Introducing Awakening! With uncompromisingly modern lines and bold architectural angles, few homes have excited as much interest as Awakening in Grand Cayman

 

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Villa Emmanuel
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Cayman Kai 5 4 10 $600 Inquire Inquire
Villa Emmanuel Cayman Kai

Gather your favorite people and head to 5-bedroom, 4-bath Villa Emmanuel, on the quiet shores of Cayman Kai, near Rum Point

 

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Villa Bellagio
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Cayman Kai 5 5 12 $460 Inquire Inquire
Villa Bellagio Cayman Kai

Gather your favorite people and head to 5-bedroom, 4-bath Villa Emmanuel, on the quiet shores of Cayman Kai, near Rum Point

 

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Villa Blanca
Location Beds Baths Sleeps Weekly Low Nightly High Nightly Peak
Grand Cayman 5 5 10 $799 $8,255 $11,970
Ecstasea Cayman Kai Grand Cayman

Villa Blanca, Cayman Islands, with over 7,000 sq. feet offers the most stunning views from every room, with crystal blue waters and privacy beyond compare. The house sits above a private small beach which can be accessed via path, it’s a truly spectacular way, as many clients would agree, of enjoying the Caribbean and all it has to offer.

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Pease Bay House
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Grand Cayman 5 5.5 12 14,153 18,458 Inquire
Pease Bay House Prospect Point Grand Cayman

This elegant 5 bed, 5 bath residence is located 20 minutes drive from the airport and George Town, along our Island's quiet and scenic South shoreline. It is luxuriously landscaped, beautifully furnished and has a magnificent view across the infinity pool, beach and warm waters of the sparkling tropical sea.

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Treasure Cove
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Cayman Kai 6 4 15 $750 15,120 Inquire
Treasure Cove Grand Cayman, Vacation Rental

A fantastic place for reunions with friends or family at this secluded, crown-jewel property situated near land’s end beside the calm waters of Cayman Kai.

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On The Rocks
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
South Coast 6 4 12 $570 Inquire Inquire
On The Rocks Cayman Kai Grand Cayman

Proudly resting on the Beach Bay bluff over the shimmering azure Caribbean waters. This beautiful “On the Rocks” offers a rare elevation for Grand Cayman, making it a scenic paradise. Its elegantly furnished, sumptuous and spacious rooms in this deluxe villa are a delight to all.

 

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Sun Salutations
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Cayman Kai 6 5.5 12 $2,145 Inquire Inquire
Sun Salutations Cayman Kai Grand Cayman

Because morning stretches are better when they face the Caribbean Sea. Introducing Sun Salutations, an elegant, direct-oceanfront villa in Cayman Kai with five bedrooms, four baths and room for up to 12 adults (16 total if kids come along). Find minimalist style, a spacious, open floor-plan, and 36 feet of sliding glass framing your private infinity pool and the barefoot beach ahead

 

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Tranquility Cove
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
South Side 6 6.5 12 $2,145 Inquire Inquire
Tranquility Cove Cayman Kai Grand Cayman

Sweeping, clean-lined spaces meet stunning sea views at our 6-bedroom, 6.5-bathroom villa set on a large stretch of barefoot beach. Simple luxuries were carefully chosen to create breezy elegance, and walls of windows keep your gaze centered on the bright sea just steps away. We designed our outdoor living area to provide a boutique hotel experience just for your family

 

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Coco Kai
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
North Side 6 6.5 15 $400 Inquire Inquire
Coco Kai Cayman Kai Grand Cayman

Coco Kai is an upscale 6 bedroom, 6 and a half bathroom property located in the tranquil, pristine North Side of Grand Cayman, five minutes from Rum Point and Stingray City. Coco Kai is on the beautiful, white sand shore of the Caribbean Sea.

 

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Oceanus
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Frank Sound 6 7.5 14 $1,849 Inquire Inquire
Oceanus Cayman Kai Grand Cayman

Introducing Oceanus, where luxury, elegance and seclusion converge. This modern masterpiece has a contemporary design. The ocean-front mansion boasts four levels and includes its own elevator so less mobile loved ones can easily access all of the action

 

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Morning Glory
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
South Coast 7 6 14 $900 16.063 Inquire
Morning Glory Grand Cayman

Morning Glory is truly one of the most elegant residential estates on the south coast. This state-of-the art house features 5 bedrooms and 5.5 bathrooms, with a 2 bed/1 bath apartment above the garage, that all together accommodates a total of 14 people

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Our Cayman Cottage
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
East End 7 6.5 18 $950 16.063 Inquire
Our Cayman Cottage Grand Cayman

This spacious, exquisitely designed beachfront home has 7 bedrooms and 6.5 bathroom. This wonderful home can comfortably sleeps up to 20 guests

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Mayfair Estate
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
South Side 7 7 14 $1,646 16.063 Inquire
MayfairEstate Villa Seven Mile Beach Grand Cayman

Located in the heart of the Seven Mile Beach corridor, Mayfair Estate is truly a magazine-worthy luxury residence that balances stunning architecture with professionally designed spaces that help you focus on what’s important: distraction-free moments with family and friends. Expansive windows survey the poolside lounge areas, infinity pool, lush landscaping and 80 foot dock beyond

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Tatenda
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
South Side 7 7 14 $1,925 16.063 Inquire
Tatenda  Beach Grand Cayman

Imagine a colonial estate on the sea, brushed by palm fronds and fragranced by tropical plants. Picture a sandy beach you don’t have to share and lounge chairs overlooking the Caribbean Sea (and the kids as they paddle-board, kayak and snorkel the cove’s gentle waters)

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Evolution
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bodden Town 7 7 14 $1,287 16.063 Inquire
Evolution Villa Seven Mile Beach Grand Cayman

Inhale, exhale and arrive at Evolution, a seven-bedroom, seven-bath villa on a wide stretch of natural beach in the charming village of Bodden Town

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Coral Reef
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Seven Mile Beach 7 7.5 26 $2,600 16.063 Inquire
Coral Reef Villa Seven Mile Beach Grand Cayman

On prestigious Seven Mile Beach, there are very few private villas for rent. Most offerings are condominiums, hotels, or not part of the rental pool. Coral Reef, however, is one phenomenal exception.

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About Cayman Islands

The Cayman Islands can be summated in two ways, by it’s lovely and amazing beaches and entertainment and as a Leader in the Financial Banking  System, both of which they take very seriously.  You would think these 3 Caribbean Islands that make up the Cayman Islands would need the tourism dollars, but really they rely heavily on their financial infrastructure and have for some time.  Yet people flock there year after year for the sandy white beaches and the lovely amenities one can find in the Caymans.  As well the islands hold you captive with their rich history of Pirates and dubious beginnings.  It’s a wonder they are not called the Pirate Islands as some of their ancestors most certainly were Pirates of the Caribbean. 

However fun and adventurous you may be, this is one location you won’t want to escape from.  It’s a wonderful mix of relaxation and superb living. 

How to Get to Cayman Islands

Owen Roberts International Airport is the Largest Airport in the Caymans and has easy Flights from Miami or many other US and international Hubs.

Where to Rent a Car in the Caymans

Andy’s Car Rental is one of the local Car Rental Companies and easy to find at the airport.

Budget Grand Cayman is an International Car Rental Company that is also easy to find in Grand Cayman

Where to Charter a Boat For Fishing

Just Fish’n in the Cayman Islands is a Great Place to Charter a Boat and Get some great trophy fish.

Where to Charter a Boat for Scuba and Snorkeling

Captain Asley’s Water-sports offers some great scuba and snorkeling.

Great Tours Grand Cayman

Tropicana Tours offers tours of the Island makes it easy for everyone who wants to know the island.

Start the Process here