Cayman Islands Holiday Homes
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $509/Night
For 7 Nights US $3,560
1078.54 ft²
18 Guests
8 Bathrooms
Ocean View
Resort
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $329/Night
For 7 Nights US $2,302
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Ocean View
- Balcony/Terrace
- View
US $674/Night
For 7 Nights US $4,721
3000 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Pool
US $506/Night
For 7 Nights US $3,541
1700.7 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Pool
US $864/Night
For 7 Nights US $6,047
1182 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $669/Night
For 7 Nights US $4,685
7997.59 ft²
17 Guests
7 Bedrooms
8 Bathrooms
Free Cancellation
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $5,090/Night
For 7 Nights US $35,627
1039 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Hot Tub
- Pool
- Ocean View
US $280/Night
For 7 Nights US $1,960
1248.61 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $459/Night
For 7 Nights US $3,214
1300 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $875/Night
For 7 Nights US $6,123
1001.04 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Pool
- Ocean View
US $629/Night
For 7 Nights US $4,401
2400 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $977/Night
For 7 Nights US $6,836
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
- Turtle Nest Inn, Ocean View Apt, Rental Car Included, 1199/week!
- 7 Mile Beach Front Cayman Condo
- Gorgeous Detached Sandy Beachfront Villa at Azure Breeze Villas.
- Cayman Reef Resort 1 - Beach Haven
- Calypso Blue Luxury 6BR Oceanfront Villa Private Pool & Reef Grand Cayman
- #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
- 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 2598 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
1001.04 ft²
6 Guests
1 Bedroom
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $978/Night
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754 ft²
4 Guests
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1900 ft²
6 Guests
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2 Bathrooms
Ocean View
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950 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $253/Night
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1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $452/Night
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754 ft²
4 Guests
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Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $304/Night
For 7 Nights US $2,126
1767 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Hot Tub
- Fireplace/Heating
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1200 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $844/Night
For 7 Nights US $5,907
2400 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $1,065/Night
For 7 Nights US $7,455
1229 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $506/Night
For 7 Nights US $3,539
2800 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
US $1,520/Night
For 7 Nights US $10,639
754 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $408/Night
For 7 Nights US $2,857
