Caribbean Vacation Rentals with Pools
New
Condo
9.8(16 Reviews)
2 Bedrooms
2 Baths
4 Guests
Pool
Ocean View
Balcony/Terrace
View
US $342/Night
7 Nights - US $2,397
Apartment
10.0(43 Reviews)
3 Bedrooms
2 Baths
6 Guests
1076.39 ft²
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
US $249/Night
7 Nights - US $1,740
Bed & Breakfast
1 Bedroom
1 Bath
4 Guests
2153 ft²
- Pool
Kitchen
Parking
Internet
US $217/Night
7 Nights - US $1,516
New
Villa
2 Bedrooms
3 Baths
4 Guests
Private Pool- Oceanfront
- Pool
- Ocean View
US $1,913/Night
7 Nights - US $13,388
Apartment
10.0(40 Reviews)
1 Bedroom
1 Bath
2 Guests
484.38 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $73/Night
7 Nights - US $511
Apartment
2 Bedrooms
2 Baths
8 Guests
1335 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,041/Night
7 Nights - US $7,286
Apartment
10.0(33 Reviews)
1 Bedroom
1 Bath
4 Guests
269.1 ft²
Private Beach- Pool
- Ocean View
- Balcony/Terrace
US $119/Night
7 Nights - US $836
New
House
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $853/Night
7 Nights - US $5,970
Apartment
10.0(29 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
Hot Tub- Pool
- Ocean View
US $395/Night
7 Nights - US $2,767
New
Condo
2 Bedrooms
2 Baths
6 Guests
1324 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $845/Night
7 Nights - US $5,912
Apartment
10.0(23 Reviews)
1 Bedroom
1 Bath
4 Guests
602.78 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
US $186/Night
7 Nights - US $1,302
Villa
2 Bedrooms
3 Baths
4 Guests
5000 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $799/Night
7 Nights - US $5,590
Why Choose Rent By Owner for your Caribbean Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools 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 Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. 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 Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools 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 Rentals with Pools
1. What are the top Rentals With Pools 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 Rentals With Pools in Caribbean:
- Polkerris Bed & Breakfast
- Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
- Island Time 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
- Luxurious & Spacious Eagle Beach 2 Story Penthouse on 1st class Divi Resort
- Penthouse King Suite! Fully Remodeled and booking with full amenities!
2. How many Rentals With Pools are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 82454 in the Caribbean area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Caribbean.
More Rentals You May Like Near Caribbean
Apartment
1 Bedroom
1 Bath
4 Guests
883 ft²
- Pool
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- Kitchen
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New
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New
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1 Bedroom
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4 Guests
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US $413/Night
7 Nights - US $2,892
New
House
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Private Pool
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US $391/Night
7 Nights - US $2,739
New
House
2 Bedrooms
2 Baths
4 Guests
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- Private Pool
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Fireplace/Heating- Pool
US $376/Night
7 Nights - US $2,629
New
Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
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- Ocean View
US $372/Night
7 Nights - US $2,607
New
House
2 Bedrooms
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- View
US $370/Night
7 Nights - US $2,593
