Caribbean Vacation Rentals with Pools
Apartment
10.0(5 Reviews)
2 Bedrooms
3 Baths
6 Guests
Oceanfront
Pool
Ocean View
View
US $202/Night
7 Nights - US $1,417
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
Condo
1 Bedroom
2 Baths
3 Guests
- Pool
- Balcony/Terrace
Kitchen
Parking
US $217/Night
7 Nights - US $1,521
New
Apartment
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
700 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $268/Night
7 Nights - US $1,879
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
Condo
10.0(9 Reviews)
1 Bedroom
1 Bath
4 Guests
990 ft²
Hot Tub- Pool
- Balcony/Terrace
- Kitchen
US $377/Night
7 Nights - US $2,637
Apartment
10.0(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $395/Night
7 Nights - US $2,767
Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
Private Pool- Pool
- Ocean View
- Balcony/Terrace
US $388/Night
7 Nights - US $2,713
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
Condo
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1304 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $386/Night
7 Nights - US $2,701
Villa
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1722 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $452/Night
7 Nights - US $3,163
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
Caribbean Vacation Rentals with Pools Frequently Asked Questions
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 81919 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
House
10.0(21 Reviews)
7 Bedrooms
5 Baths
10 Guests
378.01 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Pool
US $170/Night
7 Nights - US $1,190
Villa
10.0(3 Reviews)
2 Bedrooms
2 Baths
2 Guests
1170 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $434/Night
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Villa
10.0(3 Reviews)
2 Bedrooms
3 Baths
6 Guests
1615 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $342/Night
7 Nights - US $2,392
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
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- Ocean View
- Balcony/Terrace
US $286/Night
7 Nights - US $2,003
Cabin
10.0(3 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $277/Night
7 Nights - US $1,941
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $265/Night
7 Nights - US $1,852
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
Pet Friendly- Kitchen
- Parking
US $65/Night
7 Nights - US $455
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $454/Night
7 Nights - US $3,176
House
10.0(2 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $366/Night
7 Nights - US $2,561
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Oceanfront
Fireplace/Heating- Pool
US $341/Night
7 Nights - US $2,390
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $290/Night
7 Nights - US $2,028
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $248/Night
7 Nights - US $1,733
