Beach house holiday rentals in Grand Cayman

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.

Location · Value · Nearby

Nature lovers paradise

A true tropical nature lovers dream on the North Side of the island. Relax with the whole family at this peaceful, newly renovated house surrounded by fruit trees and rock paths. If your travel is for romance, business, or family vacation, it's all covered here. Located across the street from the beach and close to restaurants, supermarketsand the famous Rum Point Club and Kaibo Yacht Club. Minutes from attractions such as the Cayman Crystal Caves, Queen Elizabeth ll Botanic park, Starfish Point

Family · Location · TV

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

Family · Location · Hospitality

Beach at your doorstep GV1111

Beautiful ocean front ground floor unit with a screened corner unit patio which offers wide angle views. Master bedroom features double French doors opening to the patio and private side porch. Fully equipped kitchen. Master bedroom with King bed and private bathroom, Guest room with 2 Twin beds (or convert to King bed). Safe and secure complex, 2 BBQ grills on site. Free parking, Tennis and pickle ball courts. Great for snorkeling. Excellent location, near shops, entertainment and services.

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.

Location · Family · Check-in

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

Location · Value · Wi-Fi

Casa Avi | An Artist-Designed Beach House

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.

Location · Family · Getting around

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 · Indoor spaces · Comfort

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 · Family · Wi-Fi

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.

Location · Family · Air conditioning

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.

Family · Location · Barbecue

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.

Value · Location · Accuracy