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Holiday Homes in Cayman Islands

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Top Cities in Cayman Islands

Our top choices for Cayman Islands holiday homes

1. 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
9.8 out of 10, Exceptional, (68 reviews)
"Everything was perfect for our family."
United States
Nancy N.
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

2. 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)
"Really enjoyed it. Couldn’t have been happier."
United States
James L.
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

3. 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

4. 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

5. 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, (197 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

6. 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

7. 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, (52 reviews)
"Love this place. It is so peaceful and beautiful. It had everything you need and more. Thanks to Lee and Karen our time here will be cherished forever."
United States
Mike L.
Carolina Kai - Beautiful LUXURY villa private beach near Rum Point & Starfish Pt

8. 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, (16 reviews)
"Great location’"
Canada
Renee M.
The price is NZ$310
includes taxes & fees
26 Sept - 27 Sept
Country Road, Take me Home- your own Island Cottage!

9. 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

10. 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

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

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

13. Bioluminescent Bay Villa – Steps from Rum Point Beach + FREE Kayaks & 4 Bikes!

Bioluminescent Bay Villa – Steps from Rum Point Beach + FREE Kayaks & 4 Bikes!
Rum Point
9.8 out of 10, Exceptional, (82 reviews)
"The property is beautiful. "
United States
Heather S.
Bioluminescent Bay Villa – Steps from Rum Point Beach + FREE Kayaks & 4 Bikes!

14. 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, (7 reviews)
"Nice place. Would go back anytime"
Canada
Mathieu
Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

15. 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 NZ$291
includes taxes & fees
26 Sept - 27 Sept
Slice of Paradise- 2 mins from Spotts Beach!

16. 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.

17. 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

18. 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 enjoyed the north side of the island. Its slower and quieter pace made it very relaxing. The house accommodated our family of nine very well!!!! We cooked and grilled at the house easily. We used the snorkel equipment and enjoyed the reefs right at our beach!! We also used the bikes and had fun biking to rum point! Thanks for a great stay"
United States
Joy H.
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

19. Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock

Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock
North Side
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful home! The snorkeling was wonderful!"
United States
Justine A.
Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock

20. 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
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
833
Accommodation
259 Holiday Homes
Lowest Price
NZ$291
Highest Price
NZ$310

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