Indoor-Outdoor Living at Its Finest

Indoor-Outdoor Villas
Amoraflora, Moon Kai, Cayman Castle, and Ocean Kai (pictured above left to right) highlight the best of indoor-outdoor living.


Let’s be real, you’re likely not going to be spending all your time coop up indoors on your Cayman vacation. No matter how beautiful the villa is, you’re going to want to spend the bulk of your time out in the warm Cayman sunshine.

These 10 spectacular homes capture the best of the great outdoors, from ocean views to designer pools, and are sure to leave you breathless.


Amoraflora is a modern coastal retreat with a unique flow to its design and featuring a lap pool, wrap around sun deck, and pickle ball court. Living areas and bedrooms open out onto the oceanfront deck, allowing ocean breezes and turquoise views to take center stage. The floating gazebo over the the lap pool will have you asking, “Am I outside or in?”, with its views of both the beach and pool, plus the occasional swimmer passing underneaththat’s right, guests can swim under the gazebo! This home seeks to bring the beauty of the outdoors in, and does so flawlessly through impeccable design, unending coziness, and an openness to the island’s stunning natural surroundings.

*Rates starting as low as $795 per night.*

Great Bluff Estates

Grate Bluff Estates vacation rental in Grand Cayman
Panoramic views from the upper terrace overlooking the villa’s multi-level pool deck.


Simply put, the backyard at Great Bluff Estates is astounding! This oceanfront masterpiece features multiple decks full of dining tables, couches, and loungers. Everyone can have their own little slice of paradise here! One of the best parts of this elegant multi-level backyard is the beautifully landscaped sun lawn by the beach. It’s the perfect spot for sunbathing, reading, or an afternoon cat nap. The designer feel of this home flows into the outdoors, making this home just as gorgeous on the outside as it is on the inside.

*Rates starting as low as $1,250 per night.*

Cayman Castle & Guesthouse

This Caribbean dream home looks out onto miles of crystal-clear blue waters and comes with an adjacent private beach lot with kayaks, thatched beach palapas, and loungers. The main terrace features a custom 17-foot mosaic dining table with the most stunning dinner-side views. The Castle also offers a covered outdoor patio by the pool and a waterfront stone sundeck with loungers and Adirondack chairs, perfect for stargazing or watching the ocean tides. They say a person’s home is their castle and Cayman Castle balances outdoor and indoor living perfectly.

*Rates starting as low as $1,275 per night.  Cayman Castle (5BR) and Castle Guesthouse (2BR) available for rent separately at lower rates.* 


Lush tropical landscaping and water fun is on deck at Kaiku!


This nature lover’s paradise is the perfect Caribbean hideaway in the popular resort-neighborhood of Cayman Kai. The entryway leading to the home is full of lush tropical landscaping that doubles as a privacy hedge. Blooming tropical paths and hidden sandy shores dotted with hammocks provide the perfect seaside retreat for those seeking serenity. The nursery even features an outdoor zen garden that’s sure to soothe any baby into a tranquil sleep. Kaiku’s large pool deck features a shaded pool with multiple lounging areas, and a spa to relax your troubles away.  More adventurous guests will want to take advantage of Kaiku’s dock and rent jet skis to keep behind the villa during their stay.

*Rates starting as low as $1,660 per night.*

Moon Kai

This spectacular villa boasts stunning interior design and luxury features including: an elevator, four kayaks, and six screened porches. There won’t be any fighting over who gets the bedroom with the screened balcony, because they all have one! Everyone can gather together on the living room porch to enjoy a night of board games or to admire the gorgeous sunsets of Cayman Kai.  Oh, and let’s not forget about the views from the pool!

*Rates starting as low as $2,225 per night*

Cos Kai

Come watch the sunsets from the comfort of Cos Kai’s lovely porch.


Mesmerizing views of the Caribbean pervade every inch of this fabulous 2 story villa. Both upper-level bedroom suites open onto a shared terrace providing elevated ocean and beach views. The barefoot white sand beach at Cos Kai faces west so you’re guaranteed spectacular sunsets. The oceanfront porch is screened from floor to ceiling, taking both the ocean breeze and water views to the max. With a bar, lounge and dining area, Cos Kai’s porch is the perfect spot for entertaining as the evening sun sets into the night.

*Rates starting as low as $950 per night.*

Babylon Reef

Babylon Reef has the best backyard snorkeling on the island.


Looking for a family-friendly space with killer indoor-outdoor vibes? Well look no further than Babylon Reef. The lower level master suite offers direct access to the pool and sunroom, allowing you to rise with your morning coffee and step out into paradise. A large wooden deck rings the pool and connects to the villa’s sunroom.  Babylon Reef has a sandy patch of beach with a hammock overlooking the water, and corn hole boards for a friendly game in the sun. The real attraction at Babylon Reef, however, is its proximity to some of the island’s best shallow snorkeling sites.  If you love to snorkel, you’ll want to stay here!

*Rates starting as low as $550 per night.*

Ocean Kai

This serene villa epitomizes modern seaside living. Enjoy al fresco dining under starlit skies on Ocean Kai’s veranda, which also has a breezy lounge area perfect for sunset cocktails with friends. During the day, relax by the pool overlooking the ocean or lay out on your private stretch of beach. This villa features over 5,500-square-feet of modern living space to enjoy, but you’ll feel like every moment is spent outside by the ocean.

*Rates starting as low as $1,200 per night.*

Cayman Sands

Cayman Sands' pool atrium
Cayman Sands’ pool atrium provides shade and bug-free pool hangs.


Freshwater pool? Check. Shore scuba-diving off the famous Cayman Wall? Check. Indoor-outdoor living? Check. From the pool atrium to the oceanside gazebo, Cayman Sands won’t disappoint.  Its oceanfront living area with vaulted ceilings shows off magnificent views of the pool and Caribbean waves. Follow the deck onto soft white sand and relax with the sea breeze under the shade of the oceanfront gazebo. The star of the show is the screened atrium encasing the freshwater pool and lounge area looking out on to the ocean. The atrium provides some shade but more importantly keeps the bugs away so you can maximize your pool time!

*Rates starting as low as $750 per night*


Olympus brings the outdoor elements inside with a retractable 40 foot wall that opens to the beach!


This designer contemporary villa epitomizes indoor/outdoor living. Featuring multiple bedroom terraces, a rooftop garden with an outdoor kitchen and endless views, plus an L-shaped oceanfront pool, Olympus is sure to leave you speechless upon arrival. Watching the living room’s 40 foot, floor-to-ceiling wall open onto the pool deck is a sight to behold.  It’s like having the ocean in your living room!

*Rates starting as low as $1,500 per night.*

No matter which of these beautiful homes you choose, rest assured they all have one thing in common—the warm Cayman sunshine will find them all!