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

Holiday Homes in Cayman Islands

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Cayman Islands holiday homes

A poolside area with lounge chairs, palm trees, and a view of the ocean.

1. 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 balcony with a view of the ocean and beach.

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

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
North Side
10.0 out of 10, Exceptional, (64 reviews)
"Our family thoroughly enjoyed our stay, I hope we can return again, sometime."
United States
Suzanne D.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
A pool area with lounge chairs and a wooden deck overlooking a clear blue ocean with 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, (199 reviews)
"The property was clean and Karen was quick to respond to any and all questions. It was such a great stay. Would recommend and would stay again!"
United States
Brandon K.
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
A pool area with lounge chairs and a view of the ocean.

4. 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, (107 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 resort with a white building, outdoor seating, and palm trees.

5. 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)
"The house was beautiful and the host was very responsive. We enjoyed our stay. "
United States
Patricia S.
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
A bedroom with a wooden ceiling, a bed with a blue bench, a rocking chair, and a wall with seashell decorations.

6. 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.

7. 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 covered patio with a table and chairs, a ceiling fan, and a view of the ocean.

8. 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, (66 reviews)
"Great location for a peaceful stay !"
United States
Mitchell B.
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
A covered outdoor seating area with a view of the ocean, white chairs, and a table with a blue top.

9. 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 covered outdoor dining area with a table set for two, surrounded by lush greenery and palm trees, overlooking a beach.

10. 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)
"Top rate!! A clean, quiet, well stocked property. We will definitely be returning in the future."
United States
Katrinaa W.
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
A beachfront property with a pathway leading to a covered area with chairs and umbrellas, overlooking the ocean.

11. Scuba & Family Home - Sleeps 9 in CoconutBay - DreamCayman

Scuba & Family Home - Sleeps 9 in CoconutBay - DreamCayman
Northwest Point
Scuba & Family Home - Sleeps 9 in CoconutBay - DreamCayman
A beach with white sand, a row of sun loungers, and a clear blue sky.

12. Coral Kai: Rum Point Villa on Sandy Shores with Fabulous Backyard Snorkeling

Coral Kai: Rum Point Villa on Sandy Shores with Fabulous Backyard Snorkeling
Grand Cayman
9.4 out of 10, Exceptional, (32 reviews)
"Very nice, would stay again"
United States
Charles B.
Coral Kai: Rum Point Villa on Sandy Shores with Fabulous Backyard Snorkeling
A modern living room with a large window offering a view of the ocean, a black leather sofa, a flat-screen TV, and a ceiling fan.

13. 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, (42 reviews)
"We had a wonderful stay! The house was the perfect size for our group of two couples and our kids. We loved all the amenities, especially the kayaks, cornhole boards, and beach chairs—they made exploring the island so much easier.The only downside was the seaweed on the beach directly in front of the house, which made snorkeling there difficult. However, we know that's common in the Caribbean during the summer and not something the owners can control.Overall, we loved the house, the location,...
United States
Katie M.
3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.
A spacious living area with a view of the ocean, furnished with sofas, chairs, and a wooden table.

14. Timeless Paradise: Ultra-Luxe Ocean Estate w/ Elevated Pool, Arcade Room, and Home Cinema

Timeless Paradise: Ultra-Luxe Ocean Estate w/ Elevated Pool, Arcade Room, and Home Cinema
Rum Point
10.0 out of 10, Exceptional, (2 reviews)
"We couldn’t have picked a better place to stay for our family trip that included our 9 grandchildren. The house, management & staff were all exceptional! Located on the northern side, it was peaceful & quiet, but minutes away from all the major attractions. I would highly recommend this beautiful home. "
United States
Jennifer C.
Timeless Paradise: Ultra-Luxe Ocean Estate w/ Elevated Pool, Arcade Room, and Home Cinema
A sunlit room with a glass-top table surrounded by wicker chairs, large windows offering a view of palm trees and a pool.

15. KAIBOSH the 9 to 5 2BR/2BA at Rum Point Bioluminescent Bay w/ Kayaks & Bikes

KAIBOSH the 9 to 5 2BR/2BA at Rum Point Bioluminescent Bay w/ Kayaks & Bikes
Rum Point
9.8 out of 10, Exceptional, (78 reviews)
"We really enjoyed our stay! "
United States
Melissa J.
KAIBOSH the 9 to 5 2BR/2BA at Rum Point Bioluminescent Bay w/ Kayaks & Bikes
A pool area with lounge chairs, a covered seating area, and a view of the ocean.

16. Dive, Relax & Explore 3BR Condo Near Cayman’s Best Dive Sites

Dive, Relax & Explore 3BR Condo Near Cayman’s Best Dive Sites
Northwest Point
9.8 out of 10, Exceptional, (9 reviews)
"My family and I had a great time loved the condo great place to stay- owner was responsive- "
United States
Doreen P.
Dive, Relax & Explore 3BR Condo Near Cayman’s Best Dive Sites
A beach view with a building surrounded by palm trees.

17. Pease Bay Manor is a private, secluded beachfront villa - call Cayman Villas

Pease Bay Manor is a private, secluded beachfront villa - call Cayman Villas
Bodden Town
10.0 out of 10, Exceptional, (17 reviews)
"We had a beautiful stay and property manager Sue was on it! Probably the best Property manager I have ever had!"
United States
Lisa C.
Pease Bay Manor is a private, secluded beachfront villa - call Cayman Villas
A beachfront property with a pool, palm trees, and a view of the ocean.

18. 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, (64 reviews)
"Had a great stay everything was amazing!"
United States
cheyenne z.
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!
A poolside area with lounge chairs and umbrellas, overlooking the ocean.

19. 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, (9 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 swimming pool, a covered deck, and a view of the ocean.

20. 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, (58 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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cayman Islands Hotel Reviews

Grand Cayman Marriott Beach Resort

Grand Cayman Marriott Beach Resort

8/10 Good
"Great hotel"
cecilia 3-night trip
Posted 1 hour ago
Grand Cayman Marriott Beach Resort

Find out more about Cayman Islands

Cayman Islands Holiday Homes information

Number of reviews
763
Accommodation
258 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia