Beach house vacation rentals in Cayman Islands

North Side Grand Cayman Beachfront Villa

Spacious beachfront home on Grand Cayman’s peaceful North Side. Walk out to crystal-clear water for snorkeling and paddleboarding — we provide kayaks, paddleboards, and snorkel gear. 4 en-suite bedrooms plus two sofa beds in living room, rooftop with ocean views, fast WiFi, full kitchen, and washer/dryer. Small grocery store and Over the Edge are 1 mile away. Supermarket in Savannah (~20 min). Restaurants & bars @ Kaibo & Rum Point (~15 min). Travel crib and kids’ games available. Self check-in.

Value · Family · Amenities

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

Value · Family · Kitchen

3 Bedroom Beach House with Pools

Relax in this spacious East End house, surrounded by lush landscaping and 5 cascading pools. As seen on HGTV, Neptune’s Nest is a two-story, stand-alone home in the charming, pastel-colored, East End Paradise Villas. With only 10 homes and 300 ft beach across the road, this quiet complex is far from the crowds but close to restaurants, parks, and world-class dive sites. The natural beach (water shoes a plus) is a haven for marine life, perfect for snorkeling or kayaking out to the nearby reef.

Family · Location · Laundry

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

Family · Value · Decor

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.

Location · Sleep quality · Condition

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.

Location · Family · TV

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.

Value · Location · Nearby

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.

Location · Family · Kitchen

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.

Location · Value · Check-in

Oceanside Townhome with Watersports at Fingertips!

Discover the magic of island life in this elegant 3-bedroom home nestled in a lush, secluded garden community. Spend your days floating between two pools, exploring the private beach, or snorkeling among vibrant marine life just steps away. Your patio overlooks tropical gardens and the pool, creating the perfect spot for golden Cayman sunsets. With the island’s beloved tiki bar only minutes away, this escape blends beauty, comfort, and coastal charm.

Value · Family · Parking

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!

Family · Location · Check-in

Paradise Beach House in South Sound, George Town

Paradise Beach House in South Sound, George Town Paradise Beach House is a beautiful vacation rental property located in South Sound, George Town, Grand Cayman. The house offers a spacious and luxurious living experience with its very own paradise beach and a view of the reef and famous wreck of South Sound! Please note the "Resort Fee" is the Government Tourist Tax that is charged to all international guests staying in the Cayman Islands.

Family · Location · Outdoor spaces