Old Man Bay Rentals

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150 Houses

Spacious 3-Bedroom 3-Bathroom Beachfront Condo with Heated Pool

Old Man Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$443

Great rentals within 20 miles that match your search

Coconut Cottage

Bodden Town cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$575

Boggy Sands Club on Seven Mile Beach - CORAL 1

West Bay condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 16 minutes

Price per night from

$2,299

Ocean Paradise # 5 Yellow - Affordable Luxury Home w/ pool

Rum Point villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$689

Cayman - SKY at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$397

Cayman - SAND at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$397

SMB-Grand 32. Beachside condo with pool. Remote work from Paradise.

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$386

Luxury Condo #2 on Boggy Sand Road-Garden Level

Seven Mile Beach apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$517

Boggy Sands Club - Parrot Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 16 minutes

Price per night from

$2,299

Castaway by the Sea - Cottage

Bodden Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$241

Castaway by the Sea - Lodge

Bodden Town beach hut

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$206

Cayman Reef Resort #1 - Renovated Seven Mile Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Immaculate, Convenient, Detailed - Awesome Location!” We've been to Cayman many times and this location was super for a party of two. The walking convenience to the beach and Camana Bay areas made it super. The details of manuals provided, communication with the owner, and cleanliness were all much appreciated!

Price per night from

$569

Sea Cove: Cayman Kai Villa w/ Private Dock & Waterfront Sun Deck for

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great vacation!” There were 4 of us - 2 couples - and the house was great! There were many activities near the house and the 7 mile area is only a drive away. The beach was great, very secluded!

Price per night from

$397

First Floor Oceanfront Condo in Top Location!

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$345

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$684

Gorgeous Beachfront Villa, Azure Breeze #5

North Side villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“perfect getaway for island living” My husband & I had decided to take our 3 teenagers for their first trip abroad and their first beach/ocean vacation, and a number of factors led us to choose Grand Cayman. We absolutely did not want the "resort" experience, which tends to be largely the same no matter where the resort is located. After extensive research my husband found Frank's villa and this place is what made our vacation unforgettable. The north side of the island is much quieter than the Georgetown/Seven Mile Beach area where all the cruise ships land, and it has a more unspoiled beauty. Although there were residents in the other villas, we almost always had the beach to ourselves and some of the best snorkeling on the island was right out back. Every evening the kids researched new snorkel sites to try out, and with every new site they made the same comment: "Our" backyard has better snorkeling. The fact that they considered it "our" backyard speaks to the homeyness of this villa--Frank & Del have truly thought of everything and our stay was very comfortable. I want to also point out that our family always tries to rent a house when we travel--with 2 teen boys and a teen girl, having a house is so much more enjoyable than staying at a hotel--and this is the best experience we've ever had. Frank & Del have gone out of their way to set up the villa so that any guest can enjoy it to its fullest, and Frank was a wealth of information prior to our trip. I really kept thinking he would tire of my husband's seemingly endless questions, but Frank provided so much information about the island that we were able to plan an absolutely amazing adventure!

Price per night from

$455

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Winter Getaway” This was not our first trip to Grand Cayman and we are very familiar with the island and what is available by way of accommodation. We have always been partial to the North Side. It offers the peace and tranquillity that you cannot find on 7 Mile Beach and “A Mid-Winter Night’s Dream” has definitely offered us the best experience so far. The condo was as described, very clean and so well equipped, we wanted for nothing. Definitely the best unit in the complex. We had a direct unobstructed view of the ocean and although we had planned to eat dinner at nearby restaurants, we spent most evenings dining on the lanai listing to the sounds of the ocean. Great snorkeling, very private beach and surrounding area. My husband and I highly recommend this property. Many thanks to the Lang family for sharing and a special thanks to Dan, it was a pleasure dealing with you.

Price per night from

$282

Cayman Conch Quest Beachfront Condo in Rum Point

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“A Grand Cayman Pearl for quiet enjoyment” We contacted the owner on line and received instant reponse to our inquiries and when we arrived at our designated time for a month we found everything that we had anticipated and more. The interior is bright and tropical and the kitchen was well equipment to accommodate whatever we decided to cook in house.The beds are comfortable and located so you can see, hear and smell the tropics.The snorkling off the beach is awesome when the water is calm and there are numerous sites within a short drive.Wifi TV and stereo were all there if you wished to use them. A vehicle is a must to get to enjoy the sites and venues of the island and to taste the Cayman cuisine. The management staff were at your instant call when needed. We would recommend this location and look forward to our return with family in the near future. Wayne & Mary Jane Dennis, Canada

Price per night from

$202

Cayman Reef Resort #50 - Best Value on the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great location, Great value, Great accommodations” The best way to express my wife’s and my satisfaction with this condo is, this was our third consecutive stay here. My wife and I have been coming to the Caymans off and on since 1985 and have stayed in several other accommodations over the years, but this is by far our favorite. We have had the pleasure of meeting Marc (the owner), and I am impressed with his attention to detail, helpfulness, prompt response to any questions, and his overall commitment to making his guests visits trouble free and enjoyable. The location is excellent and the beach area is as good, or better, than any other spot you will find along Seven Mile Beach. There are fine restaurants and shopping within easy walking distance of the condo, making the need for a rental car only an option not a necessity. I feel strongly that this is the best overall vacation value on the island. My wife and I see no reason to look elsewhere for our future trips to Grand Cayman.

Price per night from

$518

Cayman Reef Resort 56 - Luxury on Seven Mile Beach

Seven Mile Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“We all loved it!” We had a group of 6 women that stayed for a week in February. This was everything and more! It had everything that we needed. We were on the beach most of the time and it was awesome. The pool was nice, too, but we are beach girls and love to people watch! I would definitely recommend this to friends and families. We used the washer and dryer daily. Didn't do a lot of cooking, but there was every appliance we would need. Loved sitting on the screened in deck in the morning with coffee and just relaxing before we went out for supper. Sandy at the front desk was a great help. too.

Price per night from

$1,144

Ocean front Villa Grand Cayman

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 44 minutes

Price per night from

$460

SMB Area Private Villa From $2100/wk

West Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Really nice place” Quiet and comfy. This is the Cayman I remember from trips in the past. Lots of things within walking distance, like a grocery store, public beach and several good restaurants. Its away from the tourist area of George Town. You will need a car to get around.

Price per night from

$403

Island Gem

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Perfect Island Getaway!” My husband and I spent a week here for our honeymoon in April. We could not have asked for a more perfect getaway. Lee was responsive and resourceful right from the start. She answered all of our questions and made sure we had a thorough list of what to expect upon arrival and throughout our stay. We arrived on a Sunday afternoon and were welcomed at the Villa. We were given a tour of the Villa and had an opportunity to ask questions and get settled. The condo was better than we had expected - the photos of this property do not do it justice. The kitchen is fully equipped, living room is comfortable, bedrooms are large and the bathrooms both include a shower with great water pressure. There is a dishwasher and washer/dryer right in the unit. The entire condo is very tastefully decorated. Everything you could possibly need for a comfortable stay is here, it's just like being in your own home. The beds were comfortable with soft, clean sheets and plush pillows. There were more than enough beach and shower towels. There is a TV with cable and plenty of board games. Each room also has a large closet and has an outside balcony with seating. The balcony off the living room overlooks the pool and beach area, providing an excellent view of the property. Villas Pappagallo is secluded from the rest of the island, providing a relaxing, secluded area to refresh and rewind. There is a national park directly beside the Villas with a beautiful, natural landscape and a perfectly quiet place to walk along the beach. Seven Mile Beach is a short car ride away and Georgetown just a bit further. The entire island is accessible from Villas Pappagallo. We were so pleased to be staying in West Bay. Our two favourite restaurants were Ristorante Pappagallo and Cracked Conch, right in West Bay. Ristorante Pappagallo is just steps away from the Villa. The snorkelling and sunsets on West Bay were also highlights. We took a trip to rum point for an afternoon for snorkelling and lunch. This is an easy day trip in the car. There are so many things to see and do on the island, but we spent most of our days on the beach right out front Starfish Villa. The property was quiet and all neighbours were friendly and respectful. We cannot wait to come back to Grand Cayman. We will absolutely stay at Lee's condo at Villas Pappagallo again. I cannot think of one single disappointment or criticism. Great Vacation!!

Price per night from

$661

Cayman Reef Resort #33 - Personal Lanai Overlooking Beach & Ocean

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$569

Sea Jewel, 2BR, 2BA, oceanview villa

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$518

Ocean Paradise # 4 Green - Affordable Luxury Home w/ pool

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$689

Ocean Paradise # 3 Blue - Affordable Luxury Home w/ pool

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$528

Ocean Paradise # 2 Peach - Affordable Luxury Home w/ pool

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$528

Ocean Paradise # 1 Cream - Affordable Luxury Home w/ pool

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$528

Mediterranean Villa

West Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$287

CaymanOnTheBeach

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 8 minutes

Price per night from

$374

Right on Seven Mile Beach 3 Bed 2 Bath Condo Cayman Reef Resort #58 Grand Cayman

Seven Mile Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 18 minutes

Price per night from

$569

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$459

North Palm Villas

Savannah apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$271

Sunset Cove 2 Bed/2Bath Condo on Seven Mile Beach with Discounted Boat Charters

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$397

Boggy Sands Club - Parrot 1 - Seven Mile Beach

West Bay apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 16 minutes

Price per night from

$2,299

The Grove 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$440

Modern 1BR Apt /w Rooftop Pool + Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$379

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