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Holiday Homes in Cayman Islands

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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)
"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

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)
"Great property with a ton of supplies in the garage to support your trip. The one drawback was the seaweed on the beach though that’s just the luck of the draw with Mother Nature. Would recommend this property to anyone looking for a quiet getaway on the island."
United States
Jeff G.
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 £141
includes taxes & fees
13 Oct - 14 Oct
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. 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!

13. 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

14. 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

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 £132
includes taxes & fees
13 Oct - 14 Oct
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, (42 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 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

19. 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

20. Olympus: Luxe Villa w/ Designer Pool, Private Beach & Rooftop Lounge w/ Panoramic Views

Olympus: Luxe Villa w/ Designer Pool, Private Beach & Rooftop Lounge w/ Panoramic Views
Grand Cayman
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home and wonderful location!"
United States
Rob T.
Olympus: Luxe Villa w/ Designer Pool, Private Beach & Rooftop Lounge w/ Panoramic 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: Find the Perfect Place


What is the best time to enjoy a holiday home in Cayman Islands?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in Cayman Islands?

Choose from 259 beautiful holiday homes in Cayman Islands for your getaway.


How much is a holiday home in Cayman Islands?

You can find perfect holiday homes in Cayman Islands for as low as £132 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in Cayman Islands?

Find the best deals on Cayman Islands holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in Cayman Islands?

There’s no better way to spend your well-earned holiday than in a private, cosy Cayman Islands holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Cayman Islands.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Cayman Islands holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Cayman Islands—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Cayman Islands car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Cayman Islands Holiday Homes information

Number of reviews
767
Accommodation
259 Holiday Homes
Lowest Price
£132
Highest Price
£141

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