Villa vacation rentals in Old Man Bay
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Top-rated villa rentals in Old Man Bay
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Old Man Bay villa rentals
Private villa rentals
Villa in North Side
4.87 out of 5 average rating, 53 reviewsLuxury 3bd Beach Front, # 4 Green, Stunning Views
This place was lovely. Much bigger than what appeared in the photos. Quiet and peaceful just what we needed. Easy to get to activities. The beach was great for snorkeling, lots of sea life.
Villa in North Side
4.96 out of 5 average rating, 83 reviewsCoco Kai Beach Front Villa heated pool and dock
We had a large family vacation with my siblings, their families (including 1 infant), and our parents. There were 11 of us (including the baby) and the house was perfect for our size. Everyone felt comfortable in their own rooms, and there was plenty of space to spread out. The kitchen was fantastic, as were the other living spaces. However, as evidenced from the photos, the real highlight is the amazing "backyard", including the pool (which was great for our sized group. It is not large, but it is deep), and of course the beach, dock and ocean right out from the back. Definitely recommend this house.
Villa in Rum Point
4.83 out of 5 average rating, 6 reviewsGorgeous Sandy Beachfront at Azure Breeze Villas
We enjoyed our stay at Rum Point. The ocean breeze was fabulous. Beautiful and relaxing.
Villa in North Side
4.93 out of 5 average rating, 40 reviewsVilla at the Sea Front
Tetyana's home was great. Right on the beach. Very well appointed from the stocked kitchen to beach items. It's on the north side of the island which is quiet. There were several good restaurants nearby as well as the Rum Point section with a nice beach and adjacent place to eat. The island is small so nothing is that far of a drive away. Finally, Tetyana was very responsive to questions.
Villa in East End
4.93 out of 5 average rating, 43 reviewsOCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas
Kab was a great host and her local contacts were also great to interact with. The condo is great, plenty of bedroom and bathroom space. Kitchen had everything needed for cooking meals. The pools were fun to hang out at and swim in (though not heated, so the little ones could only enjoy for a short time), but they were refreshing for adults in the hot Cayman sun. The beach across the street has some nice places to relax and play in the sand with the kids, can also walk up/down (shoes/sandals recommended) for different sights and finding and place to snorkel. Overall we enjoyed our stay at Kab's place on the quiet and relaxing, East End of Grand Cayman.
Villa in Bodden Town
4.86 out of 5 average rating, 22 reviewsA Beach Villa in Paradise
Ann was great to work with. She was helpful and very responsive when I reached out with questions. The condo is in a perfect area- right in the middle of the hustle and bustle and located where it didn’t take long to get to all the spots. We are looking forward to our next trip. We will definitely be reaching out to Ann to book again. Thank you!!
Villa in Rum Point
5 out of 5 average rating, 10 reviewsTarasand
What a beautiful house and amazing private beach. We loved our time out under the umbrella’ tree!!!
Villa in West Bay
4.86 out of 5 average rating, 7 reviewsCayman Breezes at Villas Pappagalo
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!
Luxury villa rentals
Villa in North Side
4.96 out of 5 average rating, 83 reviewsCoco Kai Beach Front Villa heated pool and dock
We had a large family vacation with my siblings, their families (including 1 infant), and our parents. There were 11 of us (including the baby) and the house was perfect for our size. Everyone felt comfortable in their own rooms, and there was plenty of space to spread out. The kitchen was fantastic, as were the other living spaces. However, as evidenced from the photos, the real highlight is the amazing "backyard", including the pool (which was great for our sized group. It is not large, but it is deep), and of course the beach, dock and ocean right out from the back. Definitely recommend this house.
Villa in Rum Point
5 out of 5 average rating, 10 reviewsTarasand
What a beautiful house and amazing private beach. We loved our time out under the umbrella’ tree!!!
Villa in West Bay
4.86 out of 5 average rating, 7 reviewsCayman Breezes at Villas Pappagalo
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 in George Town
4.88 out of 5 average rating, 17 reviewsAmazing Serviced 4500 sqf villa in the ♥ of 7MB
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 .
Villa in Grand Cayman
4.74 out of 5 average rating, 27 reviewsDeluxe Spacious Villa: Ultimate Getaway
This is a very nice place and perfect for multiple families. Each large room has it's own full bathroom. It's about a 10-15 min walk to 7 mile beach. This area of the beach does have some large rocks here and there and a rocky entrance, so swim shoes helped a lot. Plenty of towels, both for the unit and for the beach. One parking spot directly in front of the unit. When we were there, there were plenty of open visitor parking spots to use for our 2nd car (we were a group of 8 people). There was also an overflow lot at the beginning of the complex, so worst case the 2nd/3rd car had a 5 min walk back to the unit. It would be nice if the unit came with a few more amenities. Most of our beach rentals have come with things like beach chairs, coolers, umbrellas. We ended up having to pack all of these things while flying down. It's a bit light on dinnerware as well, but there is a dishwasher you can run (daily if you have a large group, which we did). Overall great place!
Villa in Old Man Bay
4.9 out of 5 average rating, 10 reviews4 Bedroom home on private nature reserve
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.
Villa rentals with a pool
Villa in North Side
4.87 out of 5 average rating, 53 reviewsLuxury 3bd Beach Front, # 4 Green, Stunning Views
This place was lovely. Much bigger than what appeared in the photos. Quiet and peaceful just what we needed. Easy to get to activities. The beach was great for snorkeling, lots of sea life.
Villa in North Side
4.96 out of 5 average rating, 83 reviewsCoco Kai Beach Front Villa heated pool and dock
We had a large family vacation with my siblings, their families (including 1 infant), and our parents. There were 11 of us (including the baby) and the house was perfect for our size. Everyone felt comfortable in their own rooms, and there was plenty of space to spread out. The kitchen was fantastic, as were the other living spaces. However, as evidenced from the photos, the real highlight is the amazing "backyard", including the pool (which was great for our sized group. It is not large, but it is deep), and of course the beach, dock and ocean right out from the back. Definitely recommend this house.
Villa in George Town
4.88 out of 5 average rating, 17 reviewsAmazing Serviced 4500 sqf villa in the ♥ of 7MB
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 .
Villa in East End
4.93 out of 5 average rating, 43 reviewsOCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas
Kab was a great host and her local contacts were also great to interact with. The condo is great, plenty of bedroom and bathroom space. Kitchen had everything needed for cooking meals. The pools were fun to hang out at and swim in (though not heated, so the little ones could only enjoy for a short time), but they were refreshing for adults in the hot Cayman sun. The beach across the street has some nice places to relax and play in the sand with the kids, can also walk up/down (shoes/sandals recommended) for different sights and finding and place to snorkel. Overall we enjoyed our stay at Kab's place on the quiet and relaxing, East End of Grand Cayman.
Villa in Grand Cayman
4.74 out of 5 average rating, 27 reviewsDeluxe Spacious Villa: Ultimate Getaway
This is a very nice place and perfect for multiple families. Each large room has it's own full bathroom. It's about a 10-15 min walk to 7 mile beach. This area of the beach does have some large rocks here and there and a rocky entrance, so swim shoes helped a lot. Plenty of towels, both for the unit and for the beach. One parking spot directly in front of the unit. When we were there, there were plenty of open visitor parking spots to use for our 2nd car (we were a group of 8 people). There was also an overflow lot at the beginning of the complex, so worst case the 2nd/3rd car had a 5 min walk back to the unit. It would be nice if the unit came with a few more amenities. Most of our beach rentals have come with things like beach chairs, coolers, umbrellas. We ended up having to pack all of these things while flying down. It's a bit light on dinnerware as well, but there is a dishwasher you can run (daily if you have a large group, which we did). Overall great place!
Villa in Old Man Bay
4.9 out of 5 average rating, 10 reviews4 Bedroom home on private nature reserve
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.
Villa in East End
5 out of 5 average rating, 8 reviewsCayman Wavelength - East End Paradise Villas
This place was awesome! Right on the water with the beach literally at your door! Plenty of space for our entire family, beautiful home, great pool just steps away. The water was calm because of the protective barrier reef, and the sunrises are the best we’ve ever seen! It was a 5 min drive to Tukka and the Parrot Sanctuary, 30 to Rum Point, 45 to the airport or SMB, and an hour out to the Turtle Centre. We lived the peace and tranquility of Larry’s home, and he was so friendly and responsive to all our questions before we arrived. Thank you!!
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