Villa vacation rentals in Old Man Bay

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Popular amenities for Old Man Bay villa rentals

Private villa rentals

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

ChristyRating, 5 stars1 month ago
Such a lovely, beautiful place! The beds were very comfortable and the place was very relaxing
Guest favorite
Two Adirondack chairs in white and navy blue are positioned on a tiled patio, facing the serene sea. Lush greenery borders the sandy beach, while the sky features scattered clouds against a backdrop of blue.
Villa in North Side
4.93 out of 5 average rating, 43 reviews

Villa at the Sea Front

JenRating, 5 stars1 month ago
Great place. The location is a bit remote and quiet, we enjoyed it. There is a small grocery store very close. The house is right on the beach, with beautiful sunrises, nice sand and conch shells. There is some seaweed on the beach. The place was very clean and had everything we needed. Sunscreens, life jackets, cooking oils, laundry soap, plenty of parking. We would definitely stay again Thanks
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

DanielleRating, 5 stars1 month ago
The place was perfect for our family vacation. It looks exactly as described and shown in the pictures. We had our four grandchildren with us and the place was very well stocked with pool toys, pack and play, car seat, stroller, etc. In fact, the home was very well stocked in the kitchen as well as all of the bedrooms. The kids loved playing in the pools in the complex. We needed to add on a day at the front of our stay and Kab was very accommodating. We were very happy that we stayed in the East End Area away from the hustle and bustle of the busier areas. We enjoyed being very close to Rum Point and visiting the beach there. The beach by the home isn't very children friendly and it was a bit disappointing to see all of the litter that accumulates there. One day we visited a small public beach just a few miles north of the house and had a lovely morning there with our very own private sandy beach! I would highly recommend a stay at this home for a family vacation.
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!

KristinRating, 5 stars2 months ago
Great location and tons of space! Close to many things to do but not loud. Access to pool and grill were also a big plus. Hosts were very responsive.
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

CarrieRating, 5 stars1 week ago
Calyopso Cove was a nice little apartment for my husband and I to spend 5 nights exploring the island for the first time. It had everything we needed and we liked that the grocery store, ATM, and Heritage Kitchen as well as beach were close by and walkable.
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

PelegRating, 5 stars1 week ago
The property is perfectly positioned on the island, everything is within a 20 minute drive. The beach at the property was very quiet and convenient when you want to relax and pause the island exploration. The house is equipped with everything you may need. If you like to cook they provide everything. If you want to eat out there are plenty of options in a 5-10 minute radius. I’d highly recommend this property if you want to both explore and take advantage of a beach/pool combo. Lastly, Ann was very responsive before, during and after our stay. She was very helpful when we had questions.
Luxe
A spacious living area features high vaulted ceilings with exposed wood beams. Natural light streams through fully windowed walls, enhancing the airy feel. Cozy seating is provided by plush sofas and armchairs arranged around a wooden coffee table, with a view of the surrounding greenery.
Villa in Rum Point
5 out of 5 average rating, 12 reviews

Tarasand

AaronRating, 5 stars2 weeks ago
A perfect stay. Felt right at home. Every comfort and convenience was provided for. Amazing views. The Byrd scooters in the neighborhood made it convenient to get to Starfish Point, Kaibo, and Rum Point. Lots of great outdoor tables and seating - always something in the shade.
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

KatieRating, 5 stars1 month ago
We loved staying here! It was a great place for a quick getaway if you’re okay with being a little more secluded. We really enjoyed being further away from the crowded touristy areas, but do keep in mind that it is a little bit of a drive to the nicer beaches. Even though it was secluded, it was the safest I’ve ever felt traveling, and I would highly recommend this stay to anyone who wants a peaceful place to enjoy the gorgeous weather in Grand Cayman!

Luxury villa rentals

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

ChristyRating, 5 stars1 month ago
Such a lovely, beautiful place! The beds were very comfortable and the place was very relaxing
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

OleRating, 5 stars1 week ago
The house was great and the grandkids loved the pool and the beach. Chisholm’s grocery store made it easy to get everything we needed. Jason also arranged for one of his friends, Ben, to take us on a boat trip including snorkelling and feeding stingrays which was very reasonably priced and a big success for everybody. All in all a very good trip and we can recommend Coco Kai to anybody thinking about going to the Cayman Islands.
Sliding glass doors provide a view of the beach, where colorful chairs and palm trees frame the serene ocean scene. Sunlight reflects off the water, creating a bright and inviting atmosphere in the living space.
Villa in Rum Point
4.83 out of 5 average rating, 6 reviews

Gorgeous Sandy Beachfront at Azure Breeze Villas

ChristineRating, 5 stars76 months ago
We enjoyed our stay at Rum Point. The ocean breeze was fabulous. Beautiful and relaxing.
A serene outdoor space features a refreshing swimming pool surrounded by lush greenery and tropical plants. Two lounge chairs are positioned near the pool, inviting relaxation under the sunny sky. The expansive garden is dotted with palm trees, contributing to the tranquil atmosphere.
Villa in George Town
4.88 out of 5 average rating, 17 reviews

Amazing Serviced 4500 sqf villa in the ♥ of 7MB

HarbinderRating, 5 stars3 months ago
Beautiful home, v tastefully decorated with everything you need. Gorgeous garden and lovely pool. Katia was fantastic with recommendations and we used them all ! Great to have cleaning service also as part of rental . Much appreciated .
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!

KristinRating, 5 stars2 months ago
Great location and tons of space! Close to many things to do but not loud. Access to pool and grill were also a big plus. Hosts were very responsive.
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

RichRating, 5 stars21 months ago
Excellent place to stay if you like to be off the beaten path. Plenty of space for my family of 6. 30-40min to anything you wanted to do on the island. Frank was always responsive to the few questions we had along our stay. If you like a nice private place to gather the family after a long day of diving, snorkeling or beach time this is the place for you.
Luxe
A spacious living area features high vaulted ceilings with exposed wood beams. Natural light streams through fully windowed walls, enhancing the airy feel. Cozy seating is provided by plush sofas and armchairs arranged around a wooden coffee table, with a view of the surrounding greenery.
Villa in Rum Point
5 out of 5 average rating, 12 reviews

Tarasand

AaronRating, 5 stars2 weeks ago
A perfect stay. Felt right at home. Every comfort and convenience was provided for. Amazing views. The Byrd scooters in the neighborhood made it convenient to get to Starfish Point, Kaibo, and Rum Point. Lots of great outdoor tables and seating - always something in the shade.
A sandy beach is bordered by swaying palm trees, casting shadows on the soft white sand. The ocean glistens in the background under a blue sky, with a wooden pier extending into the water. Tropical villas are seen in the distance.
Villa in West Bay
4.86 out of 5 average rating, 7 reviews

Cayman Breezes at Villas Pappagalo

EmiliRating, 5 stars27 months ago
We loved our stay! There was lots of space for gathering as a family. The kitchen was sufficient for our cooking needs. Loved the updated bathrooms. Everyone in our group said their beds were comfortable. Each bedroom had a balcony with an ocean view which was a huge plus! The beach was just lovely. One thing we were just a bit disappointed with was the wind, which no one can control! It made the ocean almost too rough to get into and churned up things so the snorkeling was not great. We made a friend at the condo and she said the west side of the island tends to be windier, but some days they have no wind and when that happens the snorkeling is awesome!

Villa rentals with a pool

Superhost
A charming beachfront home is nestled amidst lush tropical foliage and swaying palm trees. The house's light-colored exterior complements the sandy beach, creating a peaceful setting. The bright blue sky and scattered clouds enhance the serene atmosphere surrounding the property.
Villa in North Side
4.87 out of 5 average rating, 55 reviews

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

ChristyRating, 5 stars1 month ago
Such a lovely, beautiful place! The beds were very comfortable and the place was very relaxing
Villa in North Side
4.95 out of 5 average rating, 88 reviews

Coco Kai Beach Front Villa heated pool and dock

OleRating, 5 stars1 week ago
The house was great and the grandkids loved the pool and the beach. Chisholm’s grocery store made it easy to get everything we needed. Jason also arranged for one of his friends, Ben, to take us on a boat trip including snorkelling and feeding stingrays which was very reasonably priced and a big success for everybody. All in all a very good trip and we can recommend Coco Kai to anybody thinking about going to the Cayman Islands.
A serene outdoor space features a refreshing swimming pool surrounded by lush greenery and tropical plants. Two lounge chairs are positioned near the pool, inviting relaxation under the sunny sky. The expansive garden is dotted with palm trees, contributing to the tranquil atmosphere.
Villa in George Town
4.88 out of 5 average rating, 17 reviews

Amazing Serviced 4500 sqf villa in the ♥ of 7MB

HarbinderRating, 5 stars3 months ago
Beautiful home, v tastefully decorated with everything you need. Gorgeous garden and lovely pool. Katia was fantastic with recommendations and we used them all ! Great to have cleaning service also as part of rental . Much appreciated .
Guest favorite
A vibrant pool area is surrounded by palm trees and colorful villas. Clear blue water reflects the sunny sky, with a waterfall feature adding a serene element. The poolside is bordered by a stone wall, creating a relaxing space for guests to enjoy.
Villa in East End
4.94 out of 5 average rating, 47 reviews

OCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas

DanielleRating, 5 stars1 month ago
The place was perfect for our family vacation. It looks exactly as described and shown in the pictures. We had our four grandchildren with us and the place was very well stocked with pool toys, pack and play, car seat, stroller, etc. In fact, the home was very well stocked in the kitchen as well as all of the bedrooms. The kids loved playing in the pools in the complex. We needed to add on a day at the front of our stay and Kab was very accommodating. We were very happy that we stayed in the East End Area away from the hustle and bustle of the busier areas. We enjoyed being very close to Rum Point and visiting the beach there. The beach by the home isn't very children friendly and it was a bit disappointing to see all of the litter that accumulates there. One day we visited a small public beach just a few miles north of the house and had a lovely morning there with our very own private sandy beach! I would highly recommend a stay at this home for a family vacation.
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!

KristinRating, 5 stars2 months ago
Great location and tons of space! Close to many things to do but not loud. Access to pool and grill were also a big plus. Hosts were very responsive.
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

RichRating, 5 stars21 months ago
Excellent place to stay if you like to be off the beaten path. Plenty of space for my family of 6. 30-40min to anything you wanted to do on the island. Frank was always responsive to the few questions we had along our stay. If you like a nice private place to gather the family after a long day of diving, snorkeling or beach time this is the place for you.
Top guest favorite
Villa in East End
5 out of 5 average rating, 10 reviews

Cayman Wavelength - East End Paradise Villas

KarenRating, 5 stars3 weeks ago
We had an amazing stay at Larry’s Place. We love the East End. We spent the week driving around to different areas to snorkel. The views from the home are spectacular day or night. Any questions, Larry is responsive and has fantastic recommendations.
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

PelegRating, 5 stars1 week ago
The property is perfectly positioned on the island, everything is within a 20 minute drive. The beach at the property was very quiet and convenient when you want to relax and pause the island exploration. The house is equipped with everything you may need. If you like to cook they provide everything. If you want to eat out there are plenty of options in a 5-10 minute radius. I’d highly recommend this property if you want to both explore and take advantage of a beach/pool combo. Lastly, Ann was very responsive before, during and after our stay. She was very helpful when we had questions.

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