Villa vacation rentals in Old Man Bay

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Top-rated villa rentals in Old Man Bay

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A bright living room features comfortable seating with ocean views through large windows. Light-colored furniture is arranged around a decorative rug, with tropical plants adding vibrant touches. The space invites relaxation while showcasing the beauty of the ocean just beyond.

Villa in Rum Point

Dreamy Oceanfront Villa Prime Location

Enjoy sweeping ocean views from this charming two-bedroom villa on the scenic north coast near Rum Point. With bright, cozy interiors and an oceanfront sun deck, Moon Glow is ideal for families, couples, and friends. Located in a protected marine park, Moon Glow offers incredible snorkeling—just bring pool shoes or fins! Wander the shore for seashells, swim, kayak, or simply unwind as you soak in breathtaking sunrises and magical moonlit nights. Every moment here is a slice of paradise.

Guest favorite

A modern living area features a sectional sofa and a comfortable armchair, complemented by a stylish coffee table. The kitchen, visible in the background, includes stainless steel appliances and white cabinetry. Soft blue walls add a serene touch, while natural light brightens the space.

Villa in West Bay

4.93 out of 5 average rating, 122 reviews

Luxury villa right across 7mile Beach + Bed Swing

1 bedroom with King size bed and Queen size sofa bed to comfortably sleep up to 4 guests. Adorable small boutique community of 7 villas a few short steps from the white sand and crystal clear water of Seven Mile Beach. Includes all the comforts of home, 50” Smart TV, FREE high-speed WiFi, Keurig Coffee Machine, AppleTV, Apple HomePod, New AC in all rooms and Walk-in closet. Condo is recently remodeled w/ new furniture. There is also custom made outdoor swing bed on the patio to relax on.

The image captures a well-maintained outdoor area surrounded by palm trees and lush greenery. A gazebo is visible, along with patio furniture arranged on a stone surface. Two colorful buildings, one peach and one yellow, are located in the background, enhancing the inviting atmosphere.

Villa in North Side

4.4 out of 5 average rating, 35 reviews

Ocean Front Private Villa, Northside Grand Cayman

Amazing Oceanfront 3 bedroom/3 bath Villa on the Northside of Grand Cayman's, excellent snorkeling in shallow waters along the beautiful protective coral reef 15 from shore, the ocean is only a few steps outside your backdoor. Mahogany Point is secluded beach front Complex on the Northside of the island, Enjoy fabulous views of the Caribbean Ocean from the family room & the master bedroom balcony. Extra amenities onsite : community pool, gazebo, lounge chairs and free parking

Luxe

An expansive balcony features modern outdoor seating with stylish cushions and wooden tables. Clear ocean views stretch to the horizon, complemented by a bright blue sky with scattered clouds. The tranquil turquoise waters create a serene backdrop for relaxation.

Villa in George Town

Fin #20 - Ocean Front Corner Penthouse

Featuring modern, contemporary designs, this serviced condominium is perfect for families or groups wanting to be on the oceanfront but away from the crowds. Guests will enjoy beautiful interiors, hotel-style amenities and in-house concierge services, so you don't have to lift a finger on vacation. The FIN concierge team will handle all your needs, including car hire via our TESLA rental program, speed boat rentals, airport pick up and drop off and maid and babysitting services.

A serene beach scene is presented with white sand and lush greenery framing the view. Palm trees sway gently in the foreground, while calm, crystal clear waters and a blue sky are visible in the background. A two-person kayak is positioned on the sand to the side.

Villa in North Side

5 out of 5 average rating, 5 reviews

Beautiful beachfront, romantic get away!

Gorgeous crystal clear waters right out the back door! Eighty feet from the sliding doors is the best snorkeling on the island, between the shore and a beautiful coral reef, in shallow water that is easy to navigate. Azure Breeze is a very quiet, cozy and private place, where you may not see more than a handful of people pass by in a day! With only six two-story units, our villa offers privacy and serenity. Many nearby restaurants and endless activities are readily available.

Superhost

A resort-style home is set amidst lush greenery and swaying palm trees, with light-colored exteriors reflecting the Caribbean sun. Lounge chairs are arranged around a pool, and the serene coastline is visible in the background, offering a relaxing beachfront escape.

Villa in North Side

4.88 out of 5 average rating, 56 reviews

Luxury 3bd Beach Front, # 4 Green, Stunning Views

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day.

Superhost

A refreshing pool is framed by lush palm trees, presenting unobstructed views of the ocean. The pool deck is spacious, featuring multiple lounge chairs and a smooth, inviting pool edge. The bright blue sky reflects on the water's surface, enhancing the serene atmosphere.

Villa in West Bay

4.93 out of 5 average rating, 15 reviews

Villas Pappagallo Oceanfront (Latitude Adjustment)

You will feel like you are on your own private island. There are many times when you are literally the only ones on the beach. It's all about the ocean views! We are steps away from both the beach and the pool. You can literally see the aqua sea from every room. We are surrounded by a coral reef which is great for snorkeling. We also have our own private pier to watch sunsets and access the ocean. Pool and pool deck were totally renovated summer of 2023!

Superhost

A private swimming pool is visible, with a clear blue surface reflecting the sky. Palm trees frame the scene, while the ocean stretches beyond, showcasing various shades of blue. The pool deck features lounge chairs and a safety marker indicating a depth of 5 feet.

Villa in Bodden Town

4.85 out of 5 average rating, 27 reviews

A Beach Villa in Paradise

Latitude Adjustment is located on the Ocean side in historic Boddentown 20 minutes east of Owen Roberts International Airport and away from the hustle and bustle of Georgetown and West Bay. A short drive to Rum Point, Starfish Point , Kaibo Yacht Club, grocery stores & restaurants. A perfect place to truly unwind by the sea. In walking distance you will find a few shops, local fish fry, bakery, and world famous The Cigar shop. Plenty of charm!

An exterior view of the vacation home features a well-maintained two-story structure with a tile roof. Tropical palm trees surround the front yard, while the Caribbean Sea and a sandy beach are visible in the distance, under a mostly cloudy sky.

Villa in North Side

4.93 out of 5 average rating, 90 reviews

Coco Kai Beach Front Villa heated pool and dock

This property is situated in the quiet, pristine area of Cayman Kai. Our home also has a heated pool and sits on the beautiful beaches of the Caribbean. This is a very private, exclusive part of beautiful Grand Cayman. Coco Kai, is an upscale private vacation home located in the tranquil, pristine Northside of Grand Cayman, five minutes from Rum Point and Stingray City. Coco Kai is on the beautiful, white sand shore of the Caribbean Sea.

Guest favorite

A sandy beach stretches along the edge of a tranquil Caribbean Sea, featuring soft waves lapping at the shore. Clear blue skies are dotted with fluffy clouds, while the distant outlines of boats can be seen on the horizon along with palm trees lining the coast.

Villa in seven mile beach, george town

5 out of 5 average rating, 11 reviews

Laguna | Relaxing Family Oasis on Seven Mile Beach

Welcome to your spacious Cayman retreat in a peaceful Seven Mile Beach complex, surrounded by lush gardens and lagoon views. Relax on two private patios where turtles visit, or stroll past the pool, hot tub, and BBQ area to a private Caribbean beach just steps away. Perfect for families, this tropical escape blends nature and comfort, with top restaurants within walking distance. Sun, sea, and serenity await in your island paradise.

A tranquil pool area is framed by lush greenery, featuring a sparkling blue pool surrounded by a sun terrace with white lounge chairs. The exterior of the home presents a modern design, with large windows offering views of the natural surroundings.

Villa in Old Man Bay

4.9 out of 5 average rating, 10 reviews

4 Bedroom home on private nature reserve

Take it easy at this unique and tranquil getaway. 4 bedroom, 3 bath home surrounded by nature. Birdwatch, relax in the pool or lounge in a hammock to the sounds of the ocean and native woodland birds. Nearby are caves, botanic park and the Mastic trail but also restaurants, gas station and grocery and liquor stores. Sandy beach across the street is great for snorkeling and also hosts turtle nesting April-August.

Guest favorite

Lush greenery frames a serene view of the ocean, complemented by tall palm trees swaying gently in the breeze. The shimmering water meets the horizon under a clear sky, while a sandy area provides a relaxing space for beachside enjoyment.

Villa in East End

4.94 out of 5 average rating, 51 reviews

OCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas

Our Villa is located in an intimate complex of 10 villas surrounding a gorgeous 5 tier swimming pool. It is found in the peaceful East End, the sleepy side of the island! Enjoy our ocean views! The 300' sandy beach across the street is included in our property!