Vacation Rentals & Condos in Grand Cayman

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568 condos

Effies Luxury Villa By The Sea with Pool

Duncans villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 9 minutes

Match: Heated pool Boat available Swimming pool

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Price per night from

$387

Anticipation Villa at The Tryall Club

Sandy Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Heated pool Boat available Swimming pool

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Price per night from

$3,911

Villa De-luxe Paradise Vacation Home

Discovery Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Heated pool Boat available Swimming pool

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Price per night from

$1,144

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Pen Hall bnb Jamaica luxury Pool & Beach

Runaway Bay house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$186

Malibu Ocean View Studio

Rose Hall apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$103

NEW ONE BEDROOM PENTHOUSE OCEANFRONT CONDO WITH AMAZING VIEWS

West Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$571

Spacious Modern Condo /w Jaw Dropping Ocean Views

West Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$571

Boggy Sands Club - Parrot Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 16 minutes

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$2,286

Conched Out: Beach House w/ Backyard Snorkeling + Private Pool

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$452

Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Cayman Dream” We rented Cayman Dream in early June of 2013. We were very happy with the house. It's exactly as the pictures show. The kitchen is very well appointed and the grounds are kept very nicely. It's located in a nice quiet area with very little traffic. Our only complaint with the house was the phone/wifi. It was out for three of the six days that we were there and even after it had been fixed we had to constantly reset while we used it. With our children back in the states, we felt really out of touch. We truly enjoyed our stay and would recommend staying there.

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$486

Great Escape: Serene Cove Villa in the Quiet Neighborhood of Cayman Kai with

Rum Point house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Best. Vacation. Ever. Amazing. Beautiful. Relaxing.” Great Escape is a beautiful home in the perfect location. A truly luxurious property with an amazing pool and a short walk to Rum Point Beach, which is fantastic. I can't say enough about the house, the pool, the beach, the island. It truly was a perfect vacation. Although it is a drive to the other side of the island, we preferred the relaxing, quiet and island feel of Cayman Kai. The photos of Great Escape are very accurate except honestly I think the pool is bigger than it looks in the photos. Grand Cayman Villas handled our reservation in a professional, timely and courteous manner. They answered all of my questions promptly. They provided lots of information about the island, the property, restaurants, car rentals, etc. Upon arrival there were a couple minor issues (not worth mentioning) but the Villa Manager answered my call immediately and things were taken care of within 20 minutes. The owners of the property were a pleasure to deal with as well. We received an email from them before our stay with helpful information about the property and the island. We spoke by phone and met in person briefly on arrival. They were nothing but helpful and friendly. Highly recommend Great Escape and Grand Cayman Villas. It might be a few years but we will definitely be back.

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$910

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

Old Man Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back yard made it great for relaxing. House has everything you need and some extras. We drove most days to Rum Point Beach( 10 minute drive) to relax, great beach. Spent a few days never leaving the property as we grilled fish we bought from local fisherman at the docks. With the big group we had, the villa suited us perfectly as there was plenty of room inside and out. I liked best the privacy and location of the house, we enjoy getting away from it all and this place gave us that. Worst part about the house is saying good bye.

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$629

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$601

Fischer's Reef: Spacious, Luxury Beach Villa w/ Heated Infinity Pool & Amazing

Rum Point house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 20

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$6,690

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$401

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$401

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$1,882

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$1,310

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$401

Willows villa

St. Ann's Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$281

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$401

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$681

White diamond bed and breakfast

Runaway Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$138

Pools of the Kai 3 - Beautiful Island House with Indoor Pool

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$372

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$1,430

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$326

Serenity Get Away

Lucea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$138

Chic View 1Bedroom, 10 mins away from the Airport

Ironshore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$195

SeaDreams Luxury Ocean Front

West Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$601

Nautical Homes Paradise

Montego Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 33 minutes

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$629

Lime Tree Villa. Canal Front

Seven Mile Beach villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$1,373

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$1,596

Just For Fun: Beach Bungalow on Glowing Bio-Luminescent Bay w/ Private Pool

Rum Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Cayman Experience!!” We just finished our 1-week vacation at Just For Fun. The cute cottage certainly lived up to our expectations. Our family cooks three meals a day at home. The kitchen and new grilling area work perfectly. The kitchen has lots of extras that make cooking anything from a quick breakfast to a gourmet meal a breeze. Plus the wet bar with the wine fridge makes for a great flow of traffic. The outside area, with a pool, deck and a screened in porch is perfect. We ate every meal outside, either in the shade or by the pool. Plus there is a cute thatched hut with 4 showers in it for that quick rinse off after a swim in the ocean or a dive. This cottage would really be perfect for a locals getaway to the North Side. It has a great dock and it is very quiet. We will be back, Steve

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$566

Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront.

East End house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$681

Northern Lights #5: 2-Story Townhome w/Backyard Snorkeling, Shared Pool + Dock

Old Man Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$338

Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage

Old Man Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

“A wonderful, relaxing paradise” I recently stayed at Cayman Sands with my husband, my in-laws, and our 2 young girls, ages 4 and 6. This home is everything we could have asked for - as gorgeous as the pictures, but even fresher (the larger bedrooms have been painted since the online photos). It was very spacious and clean, and the location was great for us - quite private (even with folks staying in the neighbouring home) but a quick drive to Rum Point, which is a great beach for families with young kids with its calm water, extended shallows and sandy bottom. We had the pool heated - well worth it - as our daughters spent long hours in the pool. The beach area is nice - although it is true the water in this area is more suited to snorkelling than swimming or wading, it was fine for us with the pool right there for the girls, and snorkelling convenient for us. There is washed up plastic garbage if you walk off the property down the beach - which is not the fault of the property managers or the island, but an unfortunate consequence of garbage mismanagement elsewhere and tides/storms washing debris onto the shore. The villa is well stocked with kitchen items, pool toys, beach towels, etc... We took a great glass-bottom boat tour from Rum Point with Red Sail Sports - to Stingray City and for a bit of snorkeling. This was a nice way to go as the boat is smaller, so fewer people and plenty of time for everyone to handle the stingrays and get photos and video without feeling rushed at all. Did some nice diving off Macabuca near the Turtle Farm - can rent gear right there. I would recommend this villa without hesitation, and hope to stay here again in the future. Cayman is a beautiful, safe island, and easy to explore since it's not too big. Jim Leavitt and his staff were wonderful to deal with throughout our searching for and booking of this villa, and provided great information to us before we arrived. The cleaning lady who came mid-week (Sharon) was friendly and efficient.

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$910

Coconut Beach: Rum Point Beach House w/Pool, Beach Cabana, & Spectacular

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$944

2 of 3 match: Boat available, Heated pool, Swimming pool

2 of 3 filters match

Price per night from

$715

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