Holiday Homes in Cayman Islands

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Top Cities in Cayman Islands

Featured Holiday Homes in Cayman Islands

Beach nearby, beach towels
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar,
9.8 out of 10, Exceptional, (34)
"The house and grounds are very clean and well maintained. The kitchen is well stocked and having the extra kitchen downstairs was wonderful. We really enjoyed every minute"
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar,
Pool
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
9.8 out of 10, Exceptional, (150)
"Everything was clean, linens were soft and comfortable, there were kayaks and snorkel equipment aplenty ~ The pool was fantastic and the beach was perfect. Loved all aspects and will definitely return!"
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Beach
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
10.0 out of 10, Exceptional, (26)
"We were very impressed with the home and location. The kayaks and snorkeling gear were a nice bonus. We would definately stay again!!"
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
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Outdoor pool, a heated pool, pool loungers
Carolina Kai - NEWLY BUILT luxury villa, private beach in Rum Point / Cayman Kai
10.0 out of 10, Exceptional, (18)
"Our group had a great time at Carolina Kai. The space is wonderful with everything you need to enjoy your stay at the property!"
Carolina Kai - NEWLY BUILT luxury villa, private beach in Rum Point / Cayman Kai
Property grounds
The peace and tranquility of this cottage Works Wonders on the soul....
10.0 out of 10, Exceptional, (48)
"We thoroughly enjoyed our stay. The property is well located and affords privacy will still be close to various attractions. The pool and beach were wonderful, and we enjoyed kayaking and paddle boarding. Would definitely stay again!"
The peace and tranquility of this cottage Works Wonders on the soul....
Outdoor pool, pool loungers
Ocean Paradise
4.0 star property
9.6 out of 10, Exceptional, (37)
"This is a super cute little group of homes with a pool on the water. Here are the things you won't know from the advertisement although you're on the water you can't swim it's covered in rocks and coral. Bring aquasocks if you plan on trying to go out on the water. The furniture in unit two in the living room needs to be replaced you sit on the couch or love seat and you sink in. Beds and pillow are very good. Ac is good. Dishwasher needs updating. If you dont know grand cayman this is a 40...
Ocean Paradise
On the beach
Gardens of the Kai #6: Two-Story Beachfront Villa w/Communal Pool + Free Kayak
10.0 out of 10, Exceptional, (17)
"No words. It was perfection. The view and the beach is stunning. Super clean. So comfortable. Loved it."
Gardens of the Kai #6: Two-Story Beachfront Villa w/Communal Pool + Free Kayak
Pool
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
9.8 out of 10, Exceptional, (46)
"We all had a wonderful stay!"
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
A heated pool
Coco Kai Beach Front Villa with Heated Pool and Private Dock
10.0 out of 10, Exceptional, (76)
"Nothing can beat the beautiful ocean views right outside your back door. We enjoyed this property with our 5 kids and 3 grandchildren (ages 1-3). Everyone had the option of going from the beach to the pool, to the kitchen for snacks, to the bed for naps all right there. The house is well equipped with most everything you need. We snorkeled around the north side and decided the snorkeling right out back was some of the best! This gave those antsy people something to do and what beautiful marine...
Coco Kai Beach Front Villa with Heated Pool and Private Dock
Terrace/patio
Slice of Paradise- 2 mins from Spotts Beach!
9.0 out of 10, Wonderful, (8)
"Shawn was an excellent host, going above and beyond to help us negotiate our way in an unfamiliar place."
The price is €164
per night
21 May - 22 May
Slice of Paradise- 2 mins from Spotts Beach!
Outdoor pool
PROMO: Waterfront Villa on Private Beach at Rum Point, 3 Free Kayaks, 4 bikes
10.0 out of 10, Exceptional, (54)
"Accurately described and amazing location, could not say enough good stuff"
PROMO: Waterfront Villa on Private Beach at Rum Point, 3 Free Kayaks, 4 bikes
Property grounds
Sea Orchard Retreat: Gated Micro-Resort Near Seven Mile Beach w/Private Pool & Heated Spa
9.8 out of 10, Exceptional, (12)
"We booked this property for a family reunion and we were all blown away. Coming from Canada, we knew we had booked something special, but the location, the units, the grounds and the staff were all above and beyond our expectstions! We all fell in love with Cayman because of our special stay. I would not hestitate to book The Sea Orchard Retreat again in the future!"
Sea Orchard Retreat: Gated Micro-Resort Near Seven Mile Beach w/Private Pool & Heated Spa
Pool
Beach Front Paradise Home. Luxurious Funishings!
10.0 out of 10, Exceptional, (51)
"We've been to several islands in the Caribbean, but keep coming back to Cayman Brac. As busy Americans always with a to do list that's longer than we can complete, we like coming to a place where there's not much to do and it forces us to relax. No beaches means no crowds, there's no traffic, the snorkeling is great (including right from the house, once we found a path free of urchins), and the pool and shaded screened porch make lounging all day so comfortable. LaRonda's place was everything we...
Beach Front Paradise Home. Luxurious Funishings!
On the beach, sun-loungers, beach towels
SPACIOUS OCEAN FRONT PROPERTY-RUM POINT DRIVE w/Private Beach. Pet Friendly....
10.0 out of 10, Exceptional, (57)
"We had a wonderful and quiet time on this property. Having the grocery store a few steps away was handy. We enjoyed the water and the snorkeling."
SPACIOUS OCEAN FRONT PROPERTY-RUM POINT DRIVE w/Private Beach. Pet Friendly....
Outdoor dining
Skai Blue: Pool, Free Kayaks, and Dock on Bio Bay.
10.0 out of 10, Exceptional, (1)
"Great"
Skai Blue: Pool, Free Kayaks, and Dock on Bio Bay.
Pool
Coral Kai: Rum Point Villa on Sandy Shores with Fabulous Backyard Snorkeling
9.2 out of 10, Wonderful, (24)
"Beautiful house, clean, great entertaining set up, plenty of room for our group of 10. Lots of things to do and see just a short distance from the house. Definitely a great relaxing experience."
Coral Kai: Rum Point Villa on Sandy Shores with Fabulous Backyard Snorkeling
On the beach, beach towels
Pools of the Kai 3 - Beautiful Island House with Indoor Pool
9.8 out of 10, Exceptional, (8)
"The property was amazing! It was well laid out and so gorgeous. We had a great time."
Pools of the Kai 3 - Beautiful Island House with Indoor Pool
Pool
Fun Family Home! *Private pool, Walk to the Beach *
10.0 out of 10, Exceptional, (21)
"We rented this property with 2 families (6 people) with kids ranging from 8-12 for a week. We rented a car to get around which is a must for this property. Close to 7 mile beach but far enough away from the crowd. There was more than enough space for everyone to come together to watch tv, hang out at the pool, and cook in the kitchen. When we wanted to wind down after being out and about, we could retreat back to our own rooms while the kids played on the xbox, watched tv in their own rooms,...
Fun Family Home! *Private pool, Walk to the Beach *
Property grounds
Ritz-Carlton Deckhouse #1: Seven Mile Beach Villa w/Pool, Boathouse, + Resort Privileges
8.0 out of 10, Very good, (1)
"Property is well furnished and quite comfortable for large groups with all the necessary amenities. Great views and close to tennis/pickleball courts. It is located some distance from resort and the golf cart commute (5 minutes) is not the most scenic. Just wish the pool would have been heated as it was too cold to utilize."
Ritz-Carlton Deckhouse #1: Seven Mile Beach Villa w/Pool, Boathouse, + Resort Privileges
Outdoor pool
White Dahlia: Modern Villa on Bio Bay w/ Pool, Spa + Kiddie Splash Pool.
10.0 out of 10, Exceptional, (4)
"This was a perfect house for small, multi-gen family with young child. Very clean, neat, with recent updated everything. Great big pool, kiddie pool and hot-tub. Everyone loved it. Nice, well tended area on Rum point, walk to beaches. The dock made boating convenient and easy. Definitely get the kayaks to paddle around, especially at night on the luminescent waters!"
White Dahlia: Modern Villa on Bio Bay w/ Pool, Spa + Kiddie Splash Pool.
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