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Holiday Homes in Cayman Islands

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Our top choices for Cayman Islands holiday homes

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
2.0 star property
North Side
10.0 out of 10, Exceptional, (26)
"Beautiful clean spot. Would recommend. "
United States
ame j.
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
Grand Cayman
9.8 out of 10, Exceptional, (19)
"We had a fantastic time at this gorgeous, peaceful property. Highly, highly recommend!"
United States
Amy W.
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club
Rum Point
10.0 out of 10, Exceptional, (1)
"Our host was very responsive and answered the few questions we had in a very timely manner."
United States
STEVE K.
Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Ocean Paradise

Ocean Paradise
4.0 star property
North Side
9.6 out of 10, Exceptional, (38)
"Wonderful property! We enjoyed our stay very much! "
United States
Ashley
Ocean Paradise

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
North Side
10.0 out of 10, Exceptional, (53)
"We have stayed in houses all around the world, and Coral Vista is the best house ever! The pool was tremendous, as was the arcade and movie room. The beds were comfortable, and the owner thought of everything, including air freshener in the bathrooms. Everything was perfect!"
United States
michael d.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Northside
10.0 out of 10, Exceptional, (74)
"Wonderful family vacation! The house and location were beautiful. We really enjoyed the pool and swimming and kayaking in the ocean right out the back door. The gazebo at the end of the dock was a great place to relax!"
United States
Melissa D.
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Rum Point
9.8 out of 10, Exceptional, (178)
"My husband and I stayed here to celebrate our 4th wedding anniversary and we had a fabulous time. The house had everything you could ever need for vacation. The area is absolutely beautiful. This place is a 10/10!!!! "
United States
Morgan A.
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Private oceanfront home with wrap-around screened porch. Unique Caymanian house.

Private oceanfront home with wrap-around screened porch. Unique Caymanian house.
North Side
10.0 out of 10, Exceptional, (29)
"My husband and I along with our two adult children stayed at this property for 7 nights. Our trip was centered around scuba diving. We like to stay on the North side for the quiet and access to diving. This place is perfect for that, but it’s also so comfortable and well-maintained. We really felt like we ere alone in our own little paradise."
United States
Jean and Glenn P.
Private oceanfront home with wrap-around screened porch. Unique Caymanian house.

Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!
Patricks Island
8.2 out of 10, Very good, (20)
"Excellent stay. Very peaceful and easy instructions "
Canada
raymond
The price is €148
includes taxes & fees
23 Jan - 24 Jan 2026
Slice of Paradise- 2 mins from Spotts Beach!

KAIBOSH 9 to 5 Waterfront Condo at Rum Point

KAIBOSH 9 to 5 Waterfront Condo at Rum Point
Rum Point
9.8 out of 10, Exceptional, (71)
"Great location on Bio Bay, across the street from Rum Point. Easy bike ride to Starfish Bay, and Kaibo restaurant. Clean, well equipped, comfortable beds. Great access to pool and kayaks for the bay."
United States
Sara B.
KAIBOSH 9 to 5 Waterfront Condo at Rum Point

Country Road, Take me Home- your own Island Cottage!

Country Road, Take me Home- your own Island Cottage!
2.0 star property
Savannah
9.4 out of 10, Exceptional, (11)
"The Shower and 5g internet stood out. It was a very pleasant stay "
United States
Cody
The price is €159
includes taxes & fees
21 Jan - 22 Jan 2026
Country Road, Take me Home- your own Island Cottage!

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Cayman Islands
9.6 out of 10, Exceptional, (46)
"We really enjoyed our stay at the Romantic Reef! The house was perfect to host our friends. The pool area/beach really made the trip! "
United States
Gina T.
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar
Rumpoint
9.8 out of 10, Exceptional, (53)
"We had a great time at Seaside. It worked out very well for our family and Grand Cayman did not disappoint. "
United States
Anonymous traveller
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
Grand Cayman
10.0 out of 10, Exceptional, (50)
"This property was even more beautiful than the pictures. The beach area was quiet and serene, and we loved taking the kayaks out every morning. The property comes with everything you need, including snorkel gear, bikes, and various beach floats. The home itself is beautifully decorated and welcoming. We’re looking forward to coming back soon."
United States
Jamie W.
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

You'So Breezy: New Beach House w/ Pool, & Backyard Snorkeling! Next to Ocean Frontiers

You'So Breezy: New Beach House w/ Pool, & Backyard Snorkeling! Next to Ocean Frontiers
Gun Bay
You'So Breezy: New Beach House w/ Pool, & Backyard Snorkeling! Next to Ocean Frontiers

Cayman Beach House - New Swimming Pool !

Cayman Beach House - New Swimming Pool !
East End
9.6 out of 10, Exceptional, (30)
"We loved staying at this house in the Cayman Islands. The property manager was also very kind and responsive."
United States
Jaimeson E.
Cayman Beach House - New Swimming Pool !

Relax Enjoy and Play

Relax Enjoy and Play
George Town
9.6 out of 10, Exceptional, (18)
"We stayed nine days and discovered the island from this extremely clean and well-appointed apartment with pleasant interior and covered terrace with BBQ. Good AC and ceiling fans securing nice indoor ambiance. "
Austria
Jens Nicolai P.
Relax Enjoy and Play

Quiet, private nature retreat with pool and ocean views.

Quiet, private nature retreat with pool and ocean views.
Old Man Bay
10.0 out of 10, Exceptional, (8)
"Spacious and well stocked house in a beautiful quiet area. Very comfortable for a party of 5.Great location off the beaten path. Thank you to our hosts for great communication and adaptability. "
United States
Maria V.
Quiet, private nature retreat with pool and ocean views.

Envision: Renovated Beach Villa w/ Private Pool, Jacuzzi, & Backyard Snorkeling

Envision: Renovated Beach Villa w/ Private Pool, Jacuzzi, & Backyard Snorkeling
2.0 star property
Grand Cayman
9.2 out of 10, Wonderful, (10)
"Clean, secluded, bliss"
United States
Craig W.
Envision: Renovated Beach Villa w/ Private Pool, Jacuzzi, & Backyard Snorkeling

Tarasand: Luxurious Seaside Villa w/Designer Interiors & Barefoot Beach

Tarasand: Luxurious Seaside Villa w/Designer Interiors & Barefoot Beach
Grand Cayman
10.0 out of 10, Exceptional, (22)
"Beautiful house, lovely location Enjoyed by all"
United States
David S.
Tarasand: Luxurious Seaside Villa w/Designer Interiors & Barefoot Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cayman Islands Hotel Reviews

Find out more about Cayman Islands

Cayman Islands Holiday Homes information

Number of reviews
663
Accommodation
264 Holiday Homes
Lowest Price
€148
Highest Price
€159

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