Holiday Homes in Cayman Islands

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cayman Islands holiday homes

Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise
4.0 star property
North Side
9.6 out of 10, Exceptional, (39 reviews)
"This is very njce place to stay. Very calm and clean property. It is just 45 minutes away from main town but great place to stay. "
United States
Mayur
The price is £501
includes taxes & fees
15 Jun - 16 Jun
Cayman Luxury Rentals at Ocean Paradise

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, (57 reviews)
"Amazing property right on the most beautiful beach - we had the best holiday !! "
United Kingdom
Adam V.
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

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, (30 reviews)
"Lovely home. Host was great, very responsive. Location is right on the water with beach. Quiet end of the island, with a few places to eat. Would recommend and stay again. "
United States
Michelle H.
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

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.

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, (80 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 Pink Beach House was everything it says in it's description and more! Karen was a very good host from the very first day I inquired to the very last hour of our stay. The communication and helpful recommendations made things go very smoothly. I have used VRBO properties for over 10 years regularly and I give the Pink Beach House a 10 out of 10. Thank you Karen!"
United States
Robert B.
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, (17 reviews)
"Awesome property right on the beach. Neighborhood was very quite and private.Will definitely book again. "
United States
Rob S.
Breakers View Beach house perfect place to relax, unwind, sun, swim, snorkel

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, (30 reviews)
"Clean room, comfortable bed, helpful and pleasant host."
United States
Maria
The price is £129
includes taxes & fees
31 May - 1 Jun
Slice of Paradise- 2 mins from Spotts Beach!

Nautilus Two – A Beachfront Condo on Seven Mile Beach - by Cayman Villas

Nautilus Two – A Beachfront Condo on Seven Mile Beach - by Cayman Villas
Seven Mile Beach
9.8 out of 10, Exceptional, (48 reviews)
"Beautiful location, clean house, easy reservation and communication!"
United States
Jennifer T.
Nautilus Two – A Beachfront Condo on Seven Mile Beach - by Cayman Villas

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, (80 reviews)
"The home is beautiful and in an ideal location, close to the beach and bay. Very comfortable accommodations!"
United States
Marcie B.
Bioluminescent Bay Villa – Steps from Rum Point Beach + FREE Kayaks & 4 Bikes!

RazorBrac SeaEsta - Private Beachfront Home

RazorBrac SeaEsta - Private Beachfront Home
Cayman Brac
10.0 out of 10, Exceptional, (33 reviews)
"We loved the location and the private beach. Both the owners and property managers were amazing! "
United States
Christine B.
RazorBrac SeaEsta - Private Beachfront Home

Hidden Treasure + Little Treasure by Grand Cayman Villas

Hidden Treasure + Little Treasure by Grand Cayman Villas
Cottage
Hidden Treasure + Little Treasure by Grand Cayman Villas

Ocean Club seaside luxury family villa

Ocean Club seaside luxury family villa
Patricks Island
Ocean Club seaside luxury family villa

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

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
North Side
10.0 out of 10, Exceptional, (59 reviews)
"Gorgeous house perfect for our family reunion"
United States
Tracy H.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

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, (81 reviews)
"We had a great stay. The house was perfect for our group of 10! We would recommend this house to others. "
United States
Kathy D.
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

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!!

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
9.6 out of 10, Exceptional, (58 reviews)
"The host was very responsive and helpful prior to our trip and during our stay. The layout of the house provided excellent group space for fun and dining as well as privacy for all at night. There was good snorkeling literally in the backyard, as well as activities and grocery within a few miles."
United States
Gabrielle S.
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

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, (99 reviews)
"Great stay! We had a family gathering with seven adults and loved the gathering space and the multiple master suites! Great ocean views! Very responsive staff and great communication! We would stay here again!!"
United States
Dan B.
Coco Kai Beach Front Villa with Heated Pool and Private Dock

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, (21 reviews)
"Great property…Great amenities…Great views… Excellent restaurants nearby… More than enough room everywhere we turned. Our family of 15 had some great experiences during Christmas Week… Far Tortuga is tops!"
United States
Joseph H.
Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock

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, (47 reviews)
"Superb property and serene location "
United Kingdom
Patrick R.
Carolina Kai - Beautiful LUXURY villa private beach near Rum Point & Starfish Pt
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.
Save an average of 15% on thousands of hotels when you're signed in

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 279 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 £129 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
1,042
Accommodation
279 Holiday Homes
Lowest Price
£129
Highest Price
£501

Explore a world of travel with Expedia