Villa vacation rentals in Old Man Bay

Find and book unique villas on Airbnb

Top-rated villa rentals in Old Man Bay

Guests agree: these villas are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A bright dining area features a large white table set for guests, with colorful plates and glasses filled with orange juice. Floor-to-ceiling windows offer a panoramic view of the ocean and palm trees, enhancing the open and airy ambiance.

Villa in Rum Point

5 out of 5 average rating, 25 reviews

Beachfront Villa w King Suites in Rum Point

Take advantage of an exclusive discount when booked through Airbnb! Discover a new way of life at So Serene; a peaceful northern coast villa with breathtaking views of the ocean. Experience Grand Cayman's premier community. Every day is an adventure. Enjoy unlimited kayaking, exploring crystal waters in our back yard, and adventures like snorkeling, hiking, or fishing charters! Amidst swaying palms, enjoy exceptional amenities such as a private chef for nights in or private yoga and massage.

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, 115 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.

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

4.87 out of 5 average rating, 55 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 resort-style pool area is surrounded by lush palm trees and vibrant flowers. Comfortable lounge chairs are positioned around the pool, which features a curved design and a waterfall accent. The sky is clear with scattered clouds, contributing to a serene atmosphere.

Villa in Grand Cayman

4.77 out of 5 average rating, 30 reviews

Luxury Villa – Steps to Beach & Poolside Bliss!

The Village of Britannia is a peaceful “community” of villas and is a terrific place to stay with the family. The Villas are more economical and more fun than hotel rooms, but still have similar amenities of resorts in Cayman Islands. There is plenty of space for the family to spread out and the children can have their own bedrooms. With unobstructed views of the expansive garden, from its own private patio, you can relax and enjoy outside dining.

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

4.84 out of 5 average rating, 25 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

4.95 out of 5 average rating, 88 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.

Superhost

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

New place to stay

Laguna | Relaxing Family Oasis

Welcome to your spacious tropical retreat for the whole family all in a lush, flower-filled complex. Enjoy pond views, swaying palms, and vibrant greenery from two private patios—where turtles often visit. Stroll past the pool, hot tub, and BBQ area to your own slice of paradise: a private beach on the crystal-clear Caribbean Sea. Top-rated restaurants are just a stone’s throw away. The perfect island escape for sun, sea, and serenity.

Guest favorite

A serene beach scene showcases an expansive stretch of soft sand meeting a calm turquoise sea. The horizon displays a mix of blues under a cloudy sky. Lush greenery is visible in the distance along the coastline, enhancing the tranquil setting.

Villa in Old Man Bay

4.9 out of 5 average rating, 63 reviews

Affordable Old Man Bay Villa #1

Old Man Bay is a quaint little cluster of homes and a church on the north side of the island. This idyllic setting, with no crowds and no noise, allows for an authentic island experience and what you've come to Cayman for: Peace, quiet and tranquility. Please Note: OUR PRICES INCLUDE THE 13% ACCOMMODATION TAX. ALSO NOTE: 7 day minimum night booking at Christmas.

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, 47 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!