Holiday Homes in Cayman Islands

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Our top choices for Cayman Islands holiday homes

3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.

3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.
Grand Cayman
10.0 out of 10, Exceptional, (37 reviews)
"Really nice place, the pictures are great but really don’t do the property justice, it was an amazing week for us. Everything about the property was excellent. Owner checked in on us via email and was an excellent host. All I can say is if you are wanting to stay in the Rum Point area you have to consider this place, it is amazing. "
United States
Dwight K.
3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.

Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise
4.0 star property
North Side
9.8 out of 10, Exceptional, (41 reviews)
"Nice property!"
United States
Jeff
The price is €590
includes taxes & fees
6 Jul - 7 Jul
Cayman Luxury Rentals at Ocean Paradise

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
10.0 out of 10, Exceptional, (31 reviews)
"All was most comfortable for our family"
United States
Lisa B.
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

The peace and tranquility of this cottage Works Wonders on the soul....

The peace and tranquility of this cottage Works Wonders on the soul....
Grand Cayman
10.0 out of 10, Exceptional, (81 reviews)
"Comfortable house for two small families. Great location if you’re looking for a quieter, less “touristy” experience. Host was very easy to work with and accomidating. Would stay again. "
United States
Colby P.
The peace and tranquility of this cottage Works Wonders on the soul....

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, (190 reviews)
"The view was amazing! And we loved our own "private" beach right off the pool deck on the quiet Northside . The communication with the property manager was excellent. We would definitely stay here again."
United States
Marla W.
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Breakers View Beach house perfect place to relax, unwind, sun, swim, snorkel

Breakers View Beach house perfect place to relax, unwind, sun, swim, snorkel
Grand Cayman
10.0 out of 10, Exceptional, (18 reviews)
"Absolutely gorgeous vacation rental. House was spotless, beds were comfy and the view can’t be beat. Would love to return in the future."
United States
Brooke C.
Breakers View Beach house perfect place to relax, unwind, sun, swim, snorkel

Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
Rum Point
10.0 out of 10, Exceptional, (57 reviews)
"A great space for a family of 4 to consider home base while exploring this side of the island. Pool was a good bonus."
United States
Jason R.
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

Newly updated luxury 4-bed, 4-bath villa with private pool and beach

Newly updated luxury 4-bed, 4-bath villa with private pool and beach
West Bay
9.8 out of 10, Exceptional, (36 reviews)
"This is a gorgeous home in a great location run by a wonderful communicative host and her great on-island staff. We’ve stayed many places, and Lisa has stocked her home with everything you could possibly need from beach toys to a complete and organized kitchen."
United States
Paula D.
Newly updated luxury 4-bed, 4-bath villa with private pool and beach

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, (31 reviews)
"Perfect stay. Great spot,"
United States
Travis G.
Private oceanfront home with wrap-around screened porch. Unique Caymanian house.

Hidden Treasure + Little Treasure by Grand Cayman Villas

Hidden Treasure + Little Treasure by Grand Cayman Villas
Cottage
10.0 out of 10, Exceptional, (1 review)
"Wonderful home and location for a family vacation for 11 adults and five children. We all had a great time and spent a lot of time in the infinity pool. Definitely would return!"
United States
Rebecca S.
Hidden Treasure + Little Treasure by Grand Cayman Villas

RazorBrac SeaEsta - Private Beachfront Home

RazorBrac SeaEsta - Private Beachfront Home
Cayman Brac
10.0 out of 10, Exceptional, (33 reviews)
"Lovely house - clean and nicely decorated. Very good amenities. Balcony is the perfect spot to gaze at the water. View from the hammock is also wonderful. "
Canada
Michelle K.
RazorBrac SeaEsta - Private Beachfront Home

Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!
Patricks Island
8.4 out of 10, Very good, (31 reviews)
"Clean room, comfortable bed, helpful and pleasant host."
United States
Maria
The price is €152
includes taxes & fees
24 Jun - 25 Jun
Slice of Paradise- 2 mins from Spotts Beach!

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

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
North Side
10.0 out of 10, Exceptional, (60 reviews)
"Our Family vacation. We had a wonderful time and it was the perfect house for our family. We had 29 people, 15 adults and 14 kids from 5 months to 12 years old. There was something for everyone. The kids always love the pool but the game rooms and movie room also hit the spot. The house was very clean and we are pretty fussy when it comes to that. The host was super accommodating throughout our booking process etc. Of course the North side is the windy side but we were able to snorkel...
United States
Lauri S.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

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

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
Grand Cayman
10.0 out of 10, Exceptional, (36 reviews)
"Great location - away from the hustle and bustle of George Town. "
United States
Michael H.
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Northside
9.8 out of 10, Exceptional, (81 reviews)
"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

Cayman Bliss - Beachfront house private Pool & Beach Sleeps 8 Family-Friendly

Cayman Bliss - Beachfront house private Pool & Beach Sleeps 8 Family-Friendly
West Bay
10.0 out of 10, Exceptional, (7 reviews)
"The host was very welcoming! The property itself was amazing. The outdoor area was beautiful! "
United States
Jennifer M.
The price is €1,469
includes taxes & fees
23 Jun - 24 Jun
Cayman Bliss - Beachfront house private Pool & Beach Sleeps 8 Family-Friendly

Carolina Kai - Beautiful LUXURY villa private beach near Rum Point & Starfish Pt

Carolina Kai - Beautiful LUXURY villa private beach near Rum Point & Starfish Pt
Rum Point
10.0 out of 10, Exceptional, (48 reviews)
"Location is perfect for Kaibo Beach (walking distance), Starfish Beach and the glorious much visited Rum Point. If you want a low key vibe this is the area to have fun without crowds and traffic. The house has everything that you wouldn't even think of. Love love the house!"
United States
Susan A.
Carolina Kai - Beautiful LUXURY villa private beach near Rum Point & Starfish Pt

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

Country Road, Take me Home- your own Island Cottage!
Savannah
9.2 out of 10, Wonderful, (15 reviews)
"Great location’"
Canada
Renee M.
The price is €161
includes taxes & fees
24 Jun - 25 Jun
Country Road, Take me Home- your own Island Cottage!

Family Townhouse Minutes to 7Mile Beach

Family Townhouse Minutes to 7Mile Beach
George Town
10.0 out of 10, Exceptional, (2 reviews)
"Great place - great location !! Perfect for our stay!!"
United States
Sean D.
The price is €287
includes taxes & fees
25 Jun - 26 Jun
Family Townhouse Minutes to 7Mile Beach

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, (9 reviews)
"Private, spacious and quiet. Easy communication with the host. Well stocked kitchen with plenty of food/spices/extras in the cupboard. We utilized the large Bluetooth speaker. Comfy beds. Thoroughly enjoyed our stay."
United States
Allison W.
Quiet, private nature retreat with pool and ocean views.
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
845
Accommodation
265 Holiday Homes
Lowest Price
€152
Highest Price
€1,469

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