Beach house holiday rentals in Cayman Islands

East End Beach House with Private Dock!

Welcome! We may be biased but we believe we have the most beautiful beach in East End and would like to share it with you. We are located down the road from Morritts and The Reef Resorts, as well as Foster's Express and Italian Kitchen. We are a short drive from Tukka restaurant as well as Taco Cantina and Eagle Rays/Ocean Frontier's Diving. Here is a quick virtual tour for our property (please remove all the"spaces"): tour.metareal .com/apps/player?asset=59549321-791c-49a1-b1cb-c8ac21ce33d8

Beachfront w/Private Dock, 50ft Pool, Theatre - Wi

Windsong is an oceanfront, 5 bedroom villa on the pristine northern coast of Grand Cayman a few miles east of the famous Rum Point Beach Club. From a private beach and dock, to expansive pool and patio space, you have everything you could want on your vacation. The renovated interior is comfortable and welcoming, with numerous essentials provided for your stay. As you pull up to the villa, you'll pass through the horseshoe driveway surrounded by the beautifully landscaped front yard. Windson

Ocean's Edge: Beachfront Home with Rooftop Views

Oceanfront property with beauty all around. Walk out your door into crystal clear water. Snorkeling, paddle boarding, kayaking, and more can be experienced steps away from your beachfront home. Nearby are grocery stores, restaurants, bars, as well as the famous attraction the Cayman Crystal Caves. The house is bright and full of space. 4 bedrooms all have attached bathrooms. YOU WILL NOT FORGET THE ROOFTOP. Plenty of outdoor furniture to sit back, relax, and enjoy the views from Ocean's Edge

Casa Avi - Calm Coastal Gem in Grand Cayman

Discover Casa-Avi an idyllic beach front oasis nestled in sea-grape trees and secluded on the edge of Bodden Town. Immerse yourself in elegant king size bedrooms, breathtaking ocean views, and art-infused living spaces curated by renowned artist Avril Ward. Savor panoramic ocean views from retractable sliding doors, enjoy direct beach access for kayaking and snorkeling adventures. Downstairs, simply unwind in the embrace of hammocks while you BBQ and refresh in the private saltwater pool.

Southern Exposure, Secluded Paradise, Cayman Brac

On the Beach! Divers paradise! Beautiful slice of heaven on the exclusive south side of Cayman Brac. Stunning views from the windows - 100 ft of beachfront to call your own. The sea on one side, and the stunning and majestic bluff across the road. Pristine with luxury features to ensure you are comfortable. Local rates available! We have a 5 night minimum but please request for shorter stays. We look forward to hosting you at our island beach home! Jen & Rick IG: southernexposurecb

Charming 2 Bdr Canal-Front Escape in Rum Point

Dragon’s Pearl is a beautifully renovated 2-bedroom, 2-bath canal-front cottage in Rum Point that blends old Cayman charm with modern comforts. Sleeping up to six adults (seven with a toddler), it offers bright open living spaces, a fully equipped kitchen, and a spacious screened patio capturing cooling trade winds. Enjoy an upper sun deck, private 40-ft dock with gazebo, kayaks, and fishing. Steps from Rum Point Beach, dining, and watersports, it’s a relaxed waterfront island retreat.

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Just a 35-minute flight from Grand Cayman, this newer oceanfront home offers stunning sea views and relaxed barefoot luxury. Large windows and an open layout showcase the pool and Caribbean, connecting the kitchen, dining, and living areas. Two king suites face the ocean with tiled baths, plus a third queen room with tropical views. Travel tip: search flights to Grand Cayman first, then book the short Cayman Brac flight separately on Cayman Airways for better fares.

Island House #16 Waterfront Condo at Rum Point

KAIBOSH the 9 to 5 (Island House #16) is a beautifully furnished two-story villa tucked along the quiet inlet cove of Rum Point. Surrounded by white sand and lush tropical landscaping, this 2-bedroom, 2-bath retreat offers private balconies, screened-in outdoor living, and direct access to the beach — perfect for families or couples looking for a relaxed island getaway. KAIBOSH your 9 to 5 schedule! Leave it all behind and escape to our beautiful island retreat.

Private, quiet oceanfront home 360 screened porch.

Breezy Bay is an oceanfront, private, single-level 3 bedroom home in North Side (Old Man Bay) perfect for your relaxing Grand Cayman vacation. Enjoy panoramic oceanfront views from this beach house with a bright, open air concept. Relax on the wraparound screened porch with two seating areas or from the oceanfront king-sized day bed, all boasting oceanfront views. Direct water access into the sea. Separate primary suite for ultimate privacy. Located on 1+ acres.

Gorgeous Beach House in Little Cayman

Situated on 160ft of private beach, this rustic beach house is the perfect place to relax and unwind in beautiful Little Cayman. Watch the sunrise from the wraparound veranda and enjoy a lazy afternoon in the hammock. This spacious beach house has everything you need for the perfect vacation, including a comfy King bed, air conditioning, Wi-Fi, Sonos speaker, BBQ grill, paddleboards, and bikes. The perfect place to enjoy the simple magic of island life.

Pools of the Kai #6 by Grand Cayman Villas

Relax under your own private, screened pool atrium at Pools of the Kai #6, a renovated 2-bedroom waterfront condo with all the island vibes. This tropical retreat offers a private pool with stunning water views, perfect for couples or families seeking a quiet getaway. Prime island experiences are just steps away: walk barefoot to The Kaibo for sunset drinks, snorkel the pier at Rum Point Club, explore Starfish Point, or take a kayak tour of the Bio-Bay.

THE ROCK HOUSE with private beach on Little Cayman

This is absolutely a get-away-from-it-all vacation! On a remote island (Little Cayman), just like Gilligan's island, you will not be disturbed by anyone. A pristine "dive" destination, plenty of fishing and lobster hunts or simply relax in the hammock at the outdoor tiki bar It will feel like you are staying on your own private island - there are a few restaurants, dive resorts and fishing tours available. You will not regret this vacation!