Vacation Rentals & Condos in Grand Cayman

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89 condos

Jamaican Styles Villa

Saint James Parish villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Boat available Pets allowed

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Price per night from

$81

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Sunset at Seawind Bay

Montego Bay studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$155

Linga-Awile - Discovery Bay 3 Bedrooms

Discovery Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$614

Siesta - Runaway Bay 5 Bedroom Beachfront - Ask about our 3 and 4 Bdrm rates

Runaway Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 1

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,070

Idleawile - Rio Bueno 6 Bedrooms - ask about our 3, 4 and 5 Bdrm rates

Discovery Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,000

Selah - Runaway Bay 4 Bedroom Beachfront

Runaway Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$2,000

Drambuie - Montego Bay 5 Bedroom

Montego Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,157

Fairway Manor - 7 Bedrooms - Montego Bay

Montego Bay house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$2,890

Fortlands Point - Discovery Bay 7 - 9 Bdrms

Discovery Bay house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$4,000

Keela Wee - Discovery Bay 6 Bedrooms beachfront

Discovery Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$2,857

Sea Grapes - Discovery Bay 6 Bedroom Beachfront

Discovery Bay house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,807

Sugar Bay - Discovery Bay 5 Bedroom Beachfront

Discovery Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$2,347

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$2,729

Makana - Discovery Bay 7 Bdrm Beachfront - Ask about 4-6 bdrm rates

Discovery Bay house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$3,843

Whispering Waters - Discovery Bay 7 Bedroom Beach

Discovery Bay house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$3,429

Bloomsvale luxurious Cozy Home away from Home & Tour

Rose Hall house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$115

Meraki Moments Villa Jamaica

Runaway Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$345

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

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$396

Rate competative, and offers more for similar rate

West Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$345

Island House at Tryall Club

Sandy Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$854

Drax Hall - Coconut Walk

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$149

Beautiful Yellowbird Villa

Silver Sands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$481

Rest Azured

Little Cayman house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$802

Reggae Moon Guest House

Falmouth guest house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$132

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$573

The Pointe

Discovery Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$745

Anticipation Villa at The Tryall Club

Sandy Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$3,916

Sailing, Montego Bay, Pool, Beach, 876, Jamaica

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$91

Blue Heaven Villa

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,148

Villa De-luxe Paradise Vacation Home

Discovery Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,148

Effies Luxury Villa By The Sea with Pool

Duncans villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 28 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$387

Boggy Sands Club- Stingray Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Heaven on Earth in Grand Cayman” The reviews and pictures don't begin to do this Boggy Sand Road property justice! We rented the ground floor unit,which was absolutely spotless, elegant, roomy, well-equipped and only a few steps to the most beautiful beach. The area is residential, private and quiet - like we had somehow privately rented Seven Mile Beach! The grounds of the property were garden-like and the pool was lovely and clean. Our rental car was nice to have but not necessary - there is a Foster's Market within a short walk of the condo, as well as a few great little restaurants (Alfresco's, Timbuctuu and Heritage Kitchen). The bus service is great - more like hailing a cab with pick-up right at the foot of the driveway. But back to the beach...the unit is equipped with 2 kayaks and a paddle board, which we enjoyed tremendously on the calm, crystal-clear waters. Cemetery Beach is right next door for some of the best snorkeling we had ever experienced. The Kittiwake Shipwreck is directly off shore for another fantastic snorkeling experience. We even enjoyed swimming with our own resident sea turtle every day! The condo unit itself was spacious and fully equipped with everything you need - beach towels, chairs, umbrella, rafts and cooler;fully-equipped, gorgeous kitchen with granite counter tops, beautiful and spacious bathrooms, and super-comfortable beds. Although our "kids" were 15, the unit would be wonderful for families with smaller children as well. I must say, the absolute best part, however, was our gracious host Morne, who made us feel like pampered family members visiting from out of town. He picked us up from the airport, made sure we had everything we needed, made great recommendations for activities and restaurants, was never intrusive but always available for anything we needed. I would (and will) vacation here again in a heartbeat, and make the highest recommendation to anyone to enjoy the vacation of a lifetime at this property! Just please don't take the week I want! ;)

Responds fast! avg. 16 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$2,289

“Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the seven mile beach strip, since we heard that was very busy. We are so grateful that we found this wonderful townhome at Rum Point. Starboard Kai was very tastefully decorated, really clean and very well stocked. They even had a complimentary water cooler for us which were so helpful. They had three kayaks with life jackets, bikes (which we never got a chance to use), laundry in the unit (just make sure you bring your own HE laundry detergent), dvd player (I am not sure if we saw any dvds, but we hardly watched any TV since were had full days), coffee maker, spices, pool towels, beach toys. The only thing we needed was food, that’s how well stocked this place was. It was so nice to be right across from a Rum Point where our boys could play in the water, without worrying about waves. The location is superb, since you have the beach right in front of the condo and the beautiful bioluminescent bay in the back. It was so nice to lounge in the lanai and see the bay. From the living room and office you had nice views of the ocean of Rum Point. Many beautiful parrots, roosters and iguanas to see here, which was really neat! We did venture towards Seven mile beach and other areas of interest but wished we had just spent more time at our home base Starboard Kai. We checked out all the top beaches on the island and found our location to be #1. Janice the owner was a delight to work with; she really goes above and beyond to accommodate her guests. We also found Bob Wagner, the property manager very helpful as well. They truly excel in customer service and were very responsive to any issue we had. We loved going to the recommended restaurants. Loved our day at Sting Ray city, with Red Sail Sports which to sign up is right across the street and leaves from Rum Point’s pier. We really liked the blue iguana sanctuary nearby. We also have great memories of feeding the ‘Pirate’ Frigate birds at Tukka, a restaurant on the east end. Going to get sticky toffee pudding and seeing the Tarpons at Calypso Grill was fantastic as well. Would highly recommend this to others and have. When we got back we showed my friends and family and were amazed how beautiful everything was. Hoping to go back soon!

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$458

Eslyn Villa Runaway Bay - A Home Away From Home...

Runaway Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$196

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$407

VILLA MARA

Mammee Bay villa

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 19

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$3,435

Private room in home in Bodden Town, Cayman Islands

Bodden Town house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Pets allowed

1 of 2 filters match

Price per night from

$150

Interstellar Pods

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Boat available, Pets allowed

1 of 2 filters match

Price per night from

$100

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