Caribbean Vacation Rentals with Pools
700 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Pool
- Ocean View
- Balcony/Terrace
US $268/Night
For 7 Nights US $1,879
1076.39 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Pool
- Ocean View
US $249/Night
For 7 Nights US $1,740
3 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Condo
- Pool
- Balcony/Terrace
- Kitchen
US $217/Night
For 7 Nights US $1,521
990 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
US $372/Night
For 7 Nights US $2,602
269.1 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Beach
- Pool
- Ocean View
US $119/Night
For 7 Nights US $836
1304 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $386/Night
For 7 Nights US $2,701
1506.95 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Pool
US $395/Night
For 7 Nights US $2,767
1722 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
US $452/Night
For 7 Nights US $3,163
602.78 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Beach
- Oceanfront
- Pool
US $186/Night
For 7 Nights US $1,302
1170 ft²
2 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
US $434/Night
For 7 Nights US $3,040
1350 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Pool
- Ocean View
US $426/Night
For 7 Nights US $2,985
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
- 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 Rentals With Pools are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 81662 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.
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378.01 ft²
10 Guests
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Ocean View
House
- Private Beach
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- Hot Tub
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1100 ft²
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2 Bathrooms
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- Pool
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- Balcony/Terrace
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4 Guests
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Ocean View
House
- Private Pool
- Pool
- Ocean View
US $367/Night
For 7 Nights US $2,568
4 Guests
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Ocean View
Cottage
- Private Pool
- Oceanfront
- Fireplace/Heating
US $341/Night
For 7 Nights US $2,390
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Pool
- Ocean View
US $290/Night
For 7 Nights US $2,028
646 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $207/Night
For 7 Nights US $1,449
710 ft²
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1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
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For 7 Nights US $1,113
