Cayman Islands Holiday Homes
Condo
10.0(284 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
Oceanfront
Hot Tub
Pool
Ocean View
AU $713/Night
7 Nights - AU $4,989
Resort
10.0(15 Reviews)
8 Baths
18 Guests
1078.54 ft²
- Oceanfront
- Hot Tub
Fireplace/Heating- Pool
AU $461/Night
7 Nights - AU $3,226
Villa
10.0(207 Reviews)
1 Bedroom
1 Bath
3 Guests
- Ocean View
Balcony/Terrace
View
Kitchen
AU $945/Night
7 Nights - AU $6,616
Villa
10.0(205 Reviews)
3 Bedrooms
3 Baths
8 Guests
3000 ft²
Private Pool- Hot Tub
- Pool
- Ocean View
AU $736/Night
7 Nights - AU $5,153
Apartment
10.0(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
1700.7 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
AU $1,211/Night
7 Nights - AU $8,474
Condo
10.0(202 Reviews)
2 Bedrooms
2 Baths
6 Guests
1182 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
AU $647/Night
7 Nights - AU $4,531
House
10.0(5 Reviews)
7 Bedrooms
8 Baths
17 Guests
7997.59 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $7,132/Night
7 Nights - AU $49,926
Condo
10.0(153 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
AU $909/Night
7 Nights - AU $6,366
House
10.0(5 Reviews)
1 Bedroom
2 Baths
6 Guests
1248.61 ft²
- Fireplace/Heating
- Pool
- View
Parking
AU $643/Night
7 Nights - AU $4,504
Condo
10.0(150 Reviews)
3 Bedrooms
3 Baths
8 Guests
2400 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
AU $1,369/Night
7 Nights - AU $9,580
Villa
10.0(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
1001.04 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $881/Night
7 Nights - AU $6,167
Condo
10.0(149 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
AU $349/Night
7 Nights - AU $2,441
Why Choose Rent By Owner for your Cayman Islands Holiday Homes?
What makes our Holiday Homes special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Cayman Islands
How to Book Your Cayman Islands Holiday Homes
What's our booking process?
Our platform allows you to browse a curated selection of holiday homes. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cayman Islands
Common Holiday Homes Amenities
What amenities can you expect?
Our Holiday Homes are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Cayman Islands
Grand Cayman
Seven Mile Beach
North Sound
North Side
Grand Cayman Beaches
Rum Point
West Bay
Brinkleys
George Town
East End
Northwest Point
Bodden Town
Frequently Asked Questions About Cayman Islands Holiday Rentals
1. What are the top Holiday Homes in Cayman Islands?
There are a lot of options in Cayman Islands. If you plan on staying in the Cayman Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Holiday Homes in Cayman Islands:
- Palm Heights
- 7 Mile Beach Front Cayman Condo
- Cayman Reef Resort 1 - Beach Haven
- Calypso Blue Luxury 6BR Oceanfront Villa Private Pool & Reef Grand Cayman
- Gorgeous Detached Sandy Beachfront Villa at Azure Breeze Villas.
- #14 Oceanfront Discovery Point Club -Fall Spec. Stay 6 & Get the 7th Night FREE!
- Sunset Cove Your Dream Vacation is Affordable on Seven Mile Beach Grand Cayman.
- Relax in coastal luxury - renovated oceanfront condo Kaibo phase 2 - B13
- Cayman White Sand Beach + Quiet Pool = Relaxation
- Stunning 4 Bedroom Condo located directly on 7 MILE BEACH. Location! Location!
2. How many Holiday Homes are available in Cayman Islands?
Currently, the total number of properties listed by RBO in 2026 is over 2609 in the Cayman Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Cayman Islands.
More Rentals You May Like Near Cayman Islands
Apartment
10.0(3 Reviews)
1 Bedroom
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $1,371/Night
7 Nights - AU $9,594
House
10.0(148 Reviews)
2 Bedrooms
2 Baths
6 Guests
1900 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
AU $493/Night
7 Nights - AU $3,452
Condo
10.0(147 Reviews)
1 Bedroom
1 Bath
4 Guests
754 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $598/Night
7 Nights - AU $4,189
Condo
10.0(141 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
AU $650/Night
7 Nights - AU $4,553
Condo
10.0(140 Reviews)
1 Bedroom
1 Bath
4 Guests
754 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $395/Night
7 Nights - AU $2,766
Condo
10.0(139 Reviews)
2 Bedrooms
2 Baths
5 Guests
1767 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $629/Night
7 Nights - AU $4,402
Condo
10.0(129 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $945/Night
7 Nights - AU $6,614
Condo
10.0(124 Reviews)
3 Bedrooms
2 Baths
6 Guests
1229 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $709/Night
7 Nights - AU $4,959
Condo
10.0(123 Reviews)
3 Bedrooms
3 Baths
8 Guests
2400 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
AU $1,399/Night
7 Nights - AU $9,791
Condo
10.0(122 Reviews)
4 Bedrooms
4 Baths
10 Guests
2800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $1,940/Night
7 Nights - AU $13,578
Condo
10.0(116 Reviews)
1 Bedroom
1 Bath
4 Guests
754 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $510/Night
7 Nights - AU $3,566
Apartment
10.0(116 Reviews)
1 Bedroom
1 Bath
4 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
AU $317/Night
7 Nights - AU $2,217
