A sailboat on calm waters during sunset with a dramatic sky.

Holiday Homes in Cayman Islands

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Top Cities in Cayman Islands

A coastal city with a beach, clear blue waters, and a distant ship.
Holiday HomesHoliday Homes

Seven Mile Beach

Seven Mile Beach
An aerial view of a coastal town with a large body of water, green hills, and a highway.
Holiday HomesHoliday Homes

West Bay

West Bay

Our top choices for Cayman Islands holiday homes

A poolside area with lounge chairs and umbrellas, overlooking the ocean.

1. 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, (8 reviews)
"The host was very welcoming! The property itself was amazing. The outdoor area was beautiful! "
United States
Jennifer M.
Cayman Bliss - Beachfront house private Pool & Beach Sleeps 8 Family-Friendly
A beachfront property with a pool, palm trees, and a view of the ocean.

2. 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, (58 reviews)
"This was an unforgettably pleasant experience! We couldn't have chosen a better place to unwind, relax and enjoy what was a truly splendid vacation! Would recommend this spot anyone interested in a relaxing getaway."
United States
Mark M.
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
A beachfront hotel with outdoor seating and palm trees.

3. 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, (196 reviews)
"Perfect little beach house and great pool!"
United States
Carrie R.
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
A swimming pool with a tiled edge, a beach with lounge chairs, and palm trees.

4. 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, (42 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
A pool area with two pools, lounge chairs, and a view of the beach and ocean.

5. Beach House ~ Beachfront Retreat with Kayaks, Pool & Hot Tub

Beach House ~ Beachfront Retreat with Kayaks, Pool & Hot Tub
Grand Cayman
8.0 out of 10, Very good, (1 review)
"The house was great and very well maintained. The beach, views, and kayaks were amazing. Our only suggestion would be to run the hot tub for a longer part of the day/night."
United States
Eric S.
Beach House ~ Beachfront Retreat with Kayaks, Pool & Hot Tub
A beachfront property with multiple buildings, a sandy pathway, and lush greenery.

6. Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise
4.0 star property
North Side
9.8 out of 10, Exceptional, (43 reviews)
"Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place."
Canada
Mustapha
Cayman Luxury Rentals at Ocean Paradise
A balcony with a view of the ocean and beach.

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

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
North Side
10.0 out of 10, Exceptional, (63 reviews)
"Was the most fantastic vacation, house was amazing."
United States
Laurie S.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
A poolside area with lounge chairs, palm trees, and a view of the ocean.

8. SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Grand Cayman
9.8 out of 10, Exceptional, (87 reviews)
"We had a great stay and really enjoyed the house! "
United States
Vickie R.
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
A pool with clear blue water, a dock, and a view of the water and palm trees.

9. 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, (51 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
A balcony with a view of the beach and ocean.

10. RazorBrac SeaEsta - Private Beachfront Home

RazorBrac SeaEsta - Private Beachfront Home
Cayman Brac
10.0 out of 10, Exceptional, (33 reviews)
"My wife and I were very happy with our decision to visit Cayman Brac and stay at RazorBrac SeaEsta. The home sits right at the water’s edge with unobstructed views, and the accommodations were exactly what we were hoping for—comfortable, well-appointed, and relaxing. Highly recommended."
United States
Kevin T.
RazorBrac SeaEsta - Private Beachfront Home

11. 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)
"Quiet and convenient, was exactly what we needed for a nights stay!!!!"
United States
Matt D.
The price is AU$239
includes taxes & fees
30 Aug - 31 Aug
Slice of Paradise- 2 mins from Spotts Beach!
An outdoor seating area with a view of the ocean, white and blue chairs, and a white table with a hanging light fixture.

12. 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, (83 reviews)
"Property was lovely Nicely furnished clean beautiful location on the beach Pool was nice"
United States
Kim F.
The peace and tranquility of this cottage Works Wonders on the soul....
A beachfront hotel with outdoor seating and palm trees.

13. Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
North Side
10.0 out of 10, Exceptional, (12 reviews)
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
A beach with palm trees, a clear blue sky, and a sandy shore.

14. 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, (65 reviews)
"Great location for a peaceful stay !"
United States
Mitchell B.
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
A pool area with lounge chairs and a view of the ocean.

15. Coco Kai Beach Front Villa with Heated Pool and Private Dock

Coco Kai Beach Front Villa with Heated Pool and Private Dock
North Side
9.8 out of 10, Exceptional, (106 reviews)
"Very clean and perfect for a large group"
United States
Jason F.
Coco Kai Beach Front Villa with Heated Pool and Private Dock
A covered outdoor dining area with a table set for two, surrounded by lush greenery and palm trees, overlooking a beach.

16. 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, (40 reviews)
"I cannot say enough great things about this property. The management team worked with us on changing dates when our flights were cancelled and made it so seamless and stress free. The house was beautiful. 10/10 would stay again!"
United States
Jordan C.
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
A beachfront property with a swimming pool, a covered deck, and a view of the ocean.

17. Parrot ise 4BR Oceanfront Villa - Pool, Tiki Bar & Secluded Beach

Parrot ise 4BR Oceanfront Villa - Pool, Tiki Bar & Secluded Beach
Rum Point
9.8 out of 10, Exceptional, (57 reviews)
"We loved the house and the quiet area. It was perfect"
United States
Tessa P.
Parrot ise 4BR Oceanfront Villa - Pool, Tiki Bar & Secluded Beach
A beach with clear turquoise water, a sandy shore, and a few trees.

18. 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, (41 reviews)
"Everything about our stay was fantastic. The property manager even came and jumpstarted our rental car for us within 10 minutes as we were trying to make it to the airport. "
United States
Colleen b.
3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.

19. 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
A pool with a wooden deck, lounge chairs, and a view of the ocean.

20. Turtle Breeze: Micro-Resort w/ Swim-Up Pool Bar + Jacuzzi & Chipping Green

Turtle Breeze: Micro-Resort w/ Swim-Up Pool Bar + Jacuzzi & Chipping Green
Barkers
Turtle Breeze: Micro-Resort w/ Swim-Up Pool Bar + Jacuzzi & Chipping Green
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

The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

10/10 Excellent
"Pool had a swim up bar, beautiful beach front property. Nice rooms, helpful staff."
Jennifer 5-night trip
Posted 6 hours ago
The Westin Grand Cayman Seven Mile Beach Resort & Spa

Find out more about Cayman Islands

Cayman Islands Holiday Homes information

Number of reviews
732
Accommodation
259 Holiday Homes
Lowest Price
AU$239
Highest Price
AU$239

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