Caribbean Holiday Homes
700 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Pool
- Ocean View
- Balcony/Terrace
CA $370/Night
For 7 Nights CA $2,589
430.56 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $116/Night
For 7 Nights CA $810
1100 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
CA $989/Night
For 7 Nights CA $6,921
3983 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
CA $589/Night
For 7 Nights CA $4,123
269.1 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Beach
- Pool
- Ocean View
CA $164/Night
For 7 Nights CA $1,152
990 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
CA $585/Night
For 7 Nights CA $4,096
10.76 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Parking
- Air Conditioner
- Internet
CA $135/Night
For 7 Nights CA $945
1304 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
CA $488/Night
For 7 Nights CA $3,413
261.92 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
Apartment
- Air Conditioner
- Internet
CA $74/Night
For 7 Nights CA $518
400 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Ocean View
CA $134/Night
For 7 Nights CA $937
1506.95 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Pool
CA $545/Night
For 7 Nights CA $3,813
1260 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $891/Night
For 7 Nights CA $6,238
Why Choose Rent By Owner for your Caribbean 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 Caribbean
How to Book Your Caribbean 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 Caribbean
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
Frequently Asked Questions About Caribbean Holiday Rentals
1. What are the top Holiday Homes in Caribbean?
There are a lot of options in Caribbean. If you plan on staying in the Caribbean area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Holiday Homes in Caribbean:
- Polkerris Bed & Breakfast
- Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
- Gray Door Apartments - Adults Only
- Island Time on Sapphire Beach, Beach level walkout, Bldg A, Backup Generator
- 1st Floor POOLSIDE/OCEAN VIEW Protected Cove & Beach-Most 10 Star Reviews on 7MB
- Palm Heights
- SEA GLASS at Sapphire Beach Unit E-206 - great views of STJ and BVIs!
- Gorgeous Beachfront Condo at the Elysian Beach Resort Pool, Tennis and More
- Grande Bay Luxury 3BR Spectacular Unobstructed View
- Penthouse King Suite! Fully Remodeled and booking with full amenities!
2. How many Holiday Homes are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 143106 in the Caribbean area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Caribbean.
More Rentals You May Like Near Caribbean
1184.03 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $280/Night
For 7 Nights CA $1,958
1450 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
CA $674/Night
For 7 Nights CA $4,718
1350 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Pool
- Ocean View
CA $588/Night
For 7 Nights CA $4,113
6 Guests
1 Bedroom
1 Bathroom
Pet Friendly
Boat Rental
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
CA $485/Night
For 7 Nights CA $3,392
1615 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
CA $443/Night
For 7 Nights CA $3,100
800 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $398/Night
For 7 Nights CA $2,787
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $394/Night
For 7 Nights CA $2,760
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Pool
- Ocean View
- Balcony/Terrace
CA $365/Night
For 7 Nights CA $2,552
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $332/Night
For 7 Nights CA $2,326
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
CA $288/Night
For 7 Nights CA $2,016
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
CA $216/Night
For 7 Nights CA $1,512
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Pet Friendly
- Kitchen
CA $90/Night
For 7 Nights CA $627
