Guesthouses Cayman Islands

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125 guest houses

Secluded Sunsets waterfront w/pool- 1 Bdrm 1rst Fl

West End guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

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Coconut Cottage

Bodden Town cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$574

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!

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Price per night from

$396

Private room in home in Bodden Town, Cayman Islands

Bodden Town house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$150

Cayman Brac's Most Beautiful Seaside Rental

Cayman Brac apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$197

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$717

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$327

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Price per night from

$345

Oceanfront Oasis

West Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$1,262

Ocean Wave: Azure

Cayman Brac apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“The best vacation my spouse and I ever shared!!” Our first trip to the Brac was the best experience we have ever shared together. The warm hospitality of the Ryan family was boundless. Our anniversary gift from the Ryan family was spent purchasing snorkeling gear. I can't thank them enough for a vacation we will never forget.The villa was situated about 50 ft. from the ocean with spectacular snorkeling and sunsets. The villa was a beautiful 2 bedroom 2 bath and comfortable. The fishing was abundant with the native camaynians as a guide. We chose this island for the lack of tourists and the privacy for our 34th anniversary. We are hopefully returning to the Brac in February 2014.

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Price per night from

$201

Ocean Wave: Indigo

Cayman Brac apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$173

North Palm Villas

Savannah apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$270

Mediterranean Villa

West Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$286

Blue Karma - Luxury Beach Cottage on Cayman Brac! Best Beach on the Island!

Cayman Brac house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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$287

Watercolors: Luxury Living on Seven Mile Beach, Cayman Islands!

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,798

Lovely Bayview 3BR Condo with Pool in Grand Cayman

George Town apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$603

Peaceful Village with transportation and local guided tour

Bodden Town apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$345

Beach Living at Island Pine Villas (BLAW)

Seven Mile Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$322

Beach Living at Island Pine Villas 'BLJW'

Seven Mile Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$343

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$684

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.

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Price per night from

$517

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!!

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Price per night from

$660

Beautiful Sea Dreams Villa

Cayman Brac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$207

Modern 1BR Apt /w Rooftop Pool + Onsite Amenities

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$378

Unique and Luxurious Oceanfront Condo on Seven Mile Beach w/ Pool!

George Town apartment

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$2,028

Exclusive Modern Luxury Beachfront Apartment on Seven Mile Beach

George Town apartment

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,798

Breathtaking Ocean View Luxury Apartment

George Town apartment

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,798

Sir Turtle Beach Villas - 4b Blue

Little Cayman villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$574

NEW ONE-BEDROOM PENTHOUSE OCEANFRONT CONDO

West Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$504

Newly Built Modern 1 Bedroom 1 Bath Condo w/ Pool Near to Diving, Beach, etc

West Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$189

Luxury 3bd Beach View, # 2 Peach, Stunning Views

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$329

Penthouse 2Bd/2Bth Oceanfront Condo-Onsite Dining

West Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$315

Beach Living at Island Pine Villas (BLP)

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$207

Beach Living at Island Pine Villas (BLJ)

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$207

Beach Living at Calypso Cove

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$316

Dive into Sunsets at The Residences

George Town apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$339

Beach Living at Villas Pappagallo BLEV

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$454

Beach Living at Island Pine Villas (BLSE)

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$230

Viewing 38 of 125
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