Caribbean Holiday Homes
House
10.0(127 Reviews)
2 Bedrooms
2 Baths
5 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
CA $354/Night
7 Nights - CA $2,480
Apartment
10.0(58 Reviews)
1 Bedroom
1 Bath
2 Guests
430.56 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $118/Night
7 Nights - CA $826
Bed & Breakfast
10.0(501 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Pool- Balcony/Terrace
CA $309/Night
7 Nights - CA $2,162
Apartment
10.0(91 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $593/Night
7 Nights - CA $4,151
Apartment
10.0(43 Reviews)
3 Bedrooms
2 Baths
6 Guests
1076.39 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $349/Night
7 Nights - CA $2,443
New
Condo
10.0(82 Reviews)
2 Bedrooms
2 Baths
6 Guests
1250 ft²
Private Pool- Oceanfront
Hot Tub- Parking
CA $767/Night
7 Nights - CA $5,368
Apartment
10.0(40 Reviews)
1 Bedroom
1 Bath
2 Guests
484.38 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $102/Night
7 Nights - CA $717
Apartment
10.0(55 Reviews)
1 Bedroom
1 Bath
2 Guests
753 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $255/Night
7 Nights - CA $1,782
Apartment
10.0(33 Reviews)
1 Bedroom
1 Bath
4 Guests
269.1 ft²
Private Beach- Parking
- Pool
- Ocean View
CA $168/Night
7 Nights - CA $1,174
New
House
10.0(47 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
CA $372/Night
7 Nights - CA $2,607
Apartment
10.0(29 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $555/Night
7 Nights - CA $3,885
New
Villa
10.0(44 Reviews)
2 Bedrooms
2 Baths
4 Guests
1670 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
CA $882/Night
7 Nights - CA $6,175
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:
- Gray Door Apartments - Adults Only
- Island Time Sapphire Beach, Beach level, great views, 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
- Penthouse King Suite! Fully Remodeled and booking with full amenities!
- Luxurious & Spacious Eagle Beach 2 Story Penthouse on 1st class Divi Resort
- On The Beach, Few Steps To The Ocean unit D-204
- Immaculate Beachfront Studio great view & location, next to Condado Marriott, PR
2. How many Holiday Homes are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 144506 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
Apartment
10.0(29 Reviews)
4 Bedrooms
4 Baths
12 Guests
261.92 ft²
Air Conditioner
Internet
CA $75/Night
7 Nights - CA $528
New
Condo
10.0(40 Reviews)
2 Bedrooms
2 Baths
4 Guests
2000 ft²
- Oceanfront
- Parking
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CA $940/Night
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New
Cottage
10.0(36 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
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- View
CA $523/Night
7 Nights - CA $3,663
New
Apartment
10.0(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
646 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $349/Night
7 Nights - CA $2,443
New
House
10.0(35 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
Kitchen- Air Conditioner
- Internet
CA $139/Night
7 Nights - CA $973
New
House
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
1 ft²
Child Friendly
CA $1,421/Night
7 Nights - CA $9,949
New
House
10.0(32 Reviews)
2 Bedrooms
3 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $914/Night
7 Nights - CA $6,398
New
Condo
10.0(31 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $520/Night
7 Nights - CA $3,637
New
Villa
10.0(28 Reviews)
1 Bedroom
1 Bath
4 Guests
614 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $371/Night
7 Nights - CA $2,596
New
Condo
10.0(28 Reviews)
1 Bedroom
1 Bath
5 Guests
872 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $301/Night
7 Nights - CA $2,108
New
Cottage
10.0(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Child Friendly
CA $534/Night
7 Nights - CA $3,736
New
Villa
10.0(25 Reviews)
2 Bedrooms
3 Baths
4 Guests
1938 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,051/Night
7 Nights - CA $7,356
