Old Man Bay Rentals

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85 Houses

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

Old Man Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$441

Great rentals within 20 miles that match your search

First Floor Oceanfront Condo in Top Location!

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$345

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$683

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

Match: Shared outdoor pool (unheated)

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Price per night from

$201

Ocean front Villa Grand Cayman

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 44 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$459

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!!

Match: Shared outdoor pool (unheated)

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Price per night from

$660

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

Rum Point villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$688

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

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$688

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

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$527

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

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$527

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

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$527

CaymanOnTheBeach

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 8 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$373

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$458

Sea Jewel, 2BR, 2BA, oceanview villa

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$517

Boggy Sands Club on Seven Mile Beach Club - Coconut 1

West Bay apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 16 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$2,295

The Grove Apt # 23 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$458

The Grove Apt # 44 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

The Grove Apt # 42 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

The Grove Apt # 46 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

The Grove Apt # 47 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

The Grove Apt # 15 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

The Grove Apt # 40 2BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$688

The Grove Apt # 45 1BR Apt /w Rooftop Pool+Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

Stunning 3 bd 2 bth Oceanfrnt Condo w/pool Sleeps8

Seven Mile Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$630

Penthouse 2BR/2BTH Apt /w Rooftop Pool Near Beach

Camana Bay apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$630

Penthouse 1BR/1BTH Apt /w Rooftop Pool Near Beach

Camana Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

Modern 1BR Apt /w Rooftop Pool + Onsite Amenities

Camana Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

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

Camana Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

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

Camana Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

Penthouse 1BR/1BTH Apt /w Rooftop Pool Near Beach

Camana Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

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

Camana Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

Perfect 4 bed 2.5 Bth Family Vacation Home w/ Pool

Grand Harbour house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$13

Luxury Canal Front 3 bedroom Townhouse w/ Pool

Camana Bay townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$919

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

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

Modern 1BR Apt /w Rooftop Pool + Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$378

Spacious 1BR/1BTH Apt /w Rooftop Pool Near Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

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

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$439

A Beach Villa Latitude Adjustment

Bodden Town villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$230

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