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 stars2 months ago
Such a lovely, beautiful place! The beds were very comfortable and the place was very relaxing
Guest favorite
A spacious outdoor patio is furnished with a large dining table surrounded by six white chairs. Palm trees and greenery provide shade, while a large umbrella enhances the seating area. The ocean is visible in the background, contributing to a relaxing atmosphere.
Villa in South Sound
4.9 out of 5 average rating, 30 reviews

Incredible Beach Front Villa!

KrisRating, 5 stars1 week ago
This was a last minute trip and it was beautiful. The highlight for me was sitting on the patio every morning and night with the breeze and the sound of the ocean. The main bedroom upstairs had a very comfortable bed and a great view of the water. The kitchen had everything we needed to cook and also we used the barbecue. I definitely recommend Jason’s place for your next vacation.
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, 45 reviews

Villa at the Sea Front

NicoleRating, 5 stars1 month ago
We were so happy to be back. Tetyana’s place was just as lovely as last year but with some lovely upgrades! We had an amazing week and look forward to coming back again. Thank you!!!!
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, 48 reviews

OCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas

MariaRating, 5 stars2 weeks ago
We had a great time staying at Kabs place. It’s a fantastic house, beautifully decorated. The oceans views were simply amazing. A lot of driving though, but can’t beat the island and serene feeling at the east end. Kab was a great host and communicated clearly and often. We loved staying at Kabs place and will stay there again!
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 stars22 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.
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
4.92 out of 5 average rating, 118 reviews

Luxury villa right across 7mile Beach + Bed Swing

IleyaRating, 5 stars1 month ago
Great location especially for the price! It's across the street from a quite beach and in a less touristy area.
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, 26 reviews

A Beach Villa in Paradise

PelegRating, 5 stars1 month 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.
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

GodefridaRating, 5 stars3 weeks ago
The home is situated in the second row from the beach which provides easy access to the beach and you're not bothered by a busy noisy beach (especially during high season). There are chairs/umbrellas to use on the beach specifically for the Laguna Bay community. The home is overlooking a nice pond with turtles. There are roosters in the neighbourhood. Friendly but noisy in the morning and will wake you up at the crack of dawn so bring some earplugs if you like to sleep in. The home is a townhouse in a row of around 5 and this is the corner lot. Neighbours were quiet and friendly. There is also a security guard on duty 24/7. It's a short walk to major grocery store (Fosters) which is situated in Camana Bay - an upscale area with lots of great restaurants overlooking the bay. The ice cream store just outside the compound is convenient and great products. Home also comes with pickle ball sets. Overall a great relaxing stay.

Luxury villa rentals

Guest favorite
A spacious outdoor patio is furnished with a large dining table surrounded by six white chairs. Palm trees and greenery provide shade, while a large umbrella enhances the seating area. The ocean is visible in the background, contributing to a relaxing atmosphere.
Villa in South Sound
4.9 out of 5 average rating, 30 reviews

Incredible Beach Front Villa!

KrisRating, 5 stars1 week ago
This was a last minute trip and it was beautiful. The highlight for me was sitting on the patio every morning and night with the breeze and the sound of the ocean. The main bedroom upstairs had a very comfortable bed and a great view of the water. The kitchen had everything we needed to cook and also we used the barbecue. I definitely recommend Jason’s place for your next vacation.
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 stars78 months ago
We enjoyed our stay at Rum Point. The ocean breeze was fabulous. Beautiful and relaxing.
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!

ChristinaRating, 5 stars38 months ago
This home is near a lot of tourist attractions. And includes everything you need to feel at home. It’s really visible in the details, like a sunscreen exchange box, cotton swabs, towel and water bins to wash and dry your feet from the sand before you come inside the house, an amazing kayak. You’ll have no regrets staying here. It’s absolutely amazing.
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, 45 reviews

Villa at the Sea Front

NicoleRating, 5 stars1 month ago
We were so happy to be back. Tetyana’s place was just as lovely as last year but with some lovely upgrades! We had an amazing week and look forward to coming back again. Thank you!!!!
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 stars22 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
A shaded patio area features two comfortable lounge chairs facing the water. Sand and pebbles cover the shore, with gentle waves lapping at the beach. Lush greenery frames the scene, providing a serene view of the ocean under a bright sky.
Villa in East End
5 out of 5 average rating, 11 reviews

Cayman Wavelength - East End Paradise Villas

EmilyRating, 5 stars1 month ago
Larry was a wonderful host. Always responsive to our questions and respectful. We loved the quiet location and the proximity to some great local restaurants. The pool area was quiet our entire trip. The views from all angle of the house were incredible of the ocean. Keep in mind, water shoes are a must if you're desiring to swim in the ocean from this property. Overall, we would happily book Larry's house again for a future trip!
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

GodefridaRating, 5 stars3 weeks ago
The home is situated in the second row from the beach which provides easy access to the beach and you're not bothered by a busy noisy beach (especially during high season). There are chairs/umbrellas to use on the beach specifically for the Laguna Bay community. The home is overlooking a nice pond with turtles. There are roosters in the neighbourhood. Friendly but noisy in the morning and will wake you up at the crack of dawn so bring some earplugs if you like to sleep in. The home is a townhouse in a row of around 5 and this is the corner lot. Neighbours were quiet and friendly. There is also a security guard on duty 24/7. It's a short walk to major grocery store (Fosters) which is situated in Camana Bay - an upscale area with lots of great restaurants overlooking the bay. The ice cream store just outside the compound is convenient and great products. Home also comes with pickle ball sets. Overall a great relaxing stay.
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 stars28 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 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 stars2 months ago
Such a lovely, beautiful place! The beds were very comfortable and the place was very relaxing
Guest favorite
A sparkling pool area is framed by lush palm trees, with lounge chairs arranged alongside. The clear blue water reflects the sky, while the ocean is visible in the background past the pool, surrounded by two residential buildings.
Villa in South Sound
4.9 out of 5 average rating, 30 reviews

Incredible Beach Front Villa!

KrisRating, 5 stars1 week ago
This was a last minute trip and it was beautiful. The highlight for me was sitting on the patio every morning and night with the breeze and the sound of the ocean. The main bedroom upstairs had a very comfortable bed and a great view of the water. The kitchen had everything we needed to cook and also we used the barbecue. I definitely recommend Jason’s place for your next vacation.
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, 48 reviews

OCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas

MariaRating, 5 stars2 weeks ago
We had a great time staying at Kabs place. It’s a fantastic house, beautifully decorated. The oceans views were simply amazing. A lot of driving though, but can’t beat the island and serene feeling at the east end. Kab was a great host and communicated clearly and often. We loved staying at Kabs place and will stay there again!
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 stars22 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, 11 reviews

Cayman Wavelength - East End Paradise Villas

EmilyRating, 5 stars1 month ago
Larry was a wonderful host. Always responsive to our questions and respectful. We loved the quiet location and the proximity to some great local restaurants. The pool area was quiet our entire trip. The views from all angle of the house were incredible of the ocean. Keep in mind, water shoes are a must if you're desiring to swim in the ocean from this property. Overall, we would happily book Larry's house again for a future trip!
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, 26 reviews

A Beach Villa in Paradise

PelegRating, 5 stars1 month 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.
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

GodefridaRating, 5 stars3 weeks ago
The home is situated in the second row from the beach which provides easy access to the beach and you're not bothered by a busy noisy beach (especially during high season). There are chairs/umbrellas to use on the beach specifically for the Laguna Bay community. The home is overlooking a nice pond with turtles. There are roosters in the neighbourhood. Friendly but noisy in the morning and will wake you up at the crack of dawn so bring some earplugs if you like to sleep in. The home is a townhouse in a row of around 5 and this is the corner lot. Neighbours were quiet and friendly. There is also a security guard on duty 24/7. It's a short walk to major grocery store (Fosters) which is situated in Camana Bay - an upscale area with lots of great restaurants overlooking the bay. The ice cream store just outside the compound is convenient and great products. Home also comes with pickle ball sets. Overall a great relaxing stay.
A swimming pool with a curved shape is surrounded by a spacious deck, featuring sun loungers and tropical landscaping. Palm trees sway gently in the breeze, while the ocean and sky provide a vibrant backdrop of blue and white.
Villa in West Bay
4.86 out of 5 average rating, 7 reviews

Cayman Breezes at Villas Pappagalo

EmiliRating, 5 stars28 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!

Destinations to explore