Experience the epitome of vacationing in luxury when you stay at one of our upscale vacation rentals with pool in the Caribbean. Our vacation rentals have been carefully selected for their unique locations, amenities, and high standard of quality, making them some of the most luxury vacation rentals in the area. The perfect backdrop for any special occasion or getaway, these vacation rentals with pools offer a combination of stunning natural beauty and luxury amenities to give you the perfect Caribbean holiday.

With our vacation rentals, you’ll have access to private swimming pools, hot tubs, gourmet kitchens, home theatre systems, terrace areas, and more. Relax by the pool or take advantage of nearby attractions like world-class golf courses, shopping malls, and beaches. Whether you’re looking for a romantic getaway or a luxurious vacation with family or friends, our vacation rentals in the Caribbean have it all. Book your stay today and experience luxury vacationing at its finest!

The Top Vacation Rentals with a Pool in the Caribbean.

1. Villa Marisol, Turks and Caicos: Located on Providenciales, this five-bedroom vacation rental with a pool offers stunning views of the Caribbean Sea from its terrace area. It boasts five bedrooms, four bathrooms, a gourmet kitchen, an outdoor dining area, and a private pool with Jacuzzi. Special features include a private boat dock and chef services. The rental price starts at $1,600 per night.

2. Casa Caribe, Dominican Republic: Situated on the beautiful Samana Peninsula, this villa features five bedrooms and four bathrooms as well as a private pool with Jacuzzi and a fully-equipped kitchen. Guests will enjoy breathtaking views of the Caribbean Sea from its terrace. Special features include a home theatre system and chef services. The rental price starts at $1,800 per night.

3. Villa Sienna, Barbados: This luxurious vacation rental with a pool is located on the picturesque coast of Barbados and features six bedrooms, six bathrooms, and a private pool with Jacuzzi. A spacious terrace area offers stunning views of the ocean while the fully-equipped kitchen is perfect for entertaining. Special features include a home movie theatre system and onsite chef services. The rental price starts at $2,000 per night.

4. Casa Del Lago, Bahamas: This vacation rental with pool is located on the island of Nassau and features four bedrooms and three bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy breathtaking views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $1,600 per night.

5. Sapphire Villa, Jamaica: Located on the beautiful coast of Negril, this vacation rental with pool offers four bedrooms, three bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Guests will enjoy stunning views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $1,400 per night.

6. Villa de Sol, Puerto Rico: This vacation rental with a pool is located in Rincon and offers five bedrooms, four bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy stunning views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $2,200 per night.

7. La Casa Azul, Dominican Republic: This vacation rental with pool is located on the east coast of Hispaniola and offers four bedrooms, three bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy stunning views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $1,800 per night.

8. Casa del Mar, Mexico: Located on the Yucatan Peninsula, this vacation rental with pool offers five bedrooms and four bathrooms as well as a private pool with Jacuzzi and a fully-equipped kitchen. Enjoy breathtaking views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $2,000 per night.
9. Casa de Luz, Aruba: This vacation rental with a pool is located on the beautiful coast of Aruba and offers six bedrooms, seven bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy stunning views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $2,400 per night.

10. Villa Romana, Dominican Republic: Located on the south coast of Hispaniola, this vacation rental with pool offers four bedrooms, three bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy breathtakingly beautiful views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $1,500 per night.

11. Oceanview Villa, Jamaica: This vacation rental with pool is located on the stunning coast of Negril and offers five bedrooms, four bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Guests will enjoy breathtakingly beautiful views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. Rental price starts at $2,300 per night.

12. Villa Marbella, Puerto Rico: Located in Rincon, this vacation rental with pool offers five bedrooms, four bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy stunning views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. Rental price starts at $2,400 per night.

13. Vista del Mar, Dominican Republic: This vacation rental with pool is located on the east coast of Hispaniola and offers four bedrooms, three bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Guests will enjoy breathtakingly beautiful views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. Rental price starts at $1,800 per night.

14. Private Beach House, Bahamas: This vacation rental with pool is located on the west coast of New Providence Island and offers five bedrooms, four bathrooms, a private pool with Jacuzzi, and a fully-equipped kitchen. Enjoy stunning views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $2,500 per night.

15. Morro Castle Villa, Cuba: Located on the north coast of Havana, this vacation rental with pool offers four bedrooms, three bathrooms, a private pool with a Jacuzzi, and a fully-equipped kitchen. Guests will enjoy breathtakingly beautiful views of the Caribbean Sea from its terrace area while taking advantage of special features like a home theatre system and chef services. The rental price starts at $1,750 per night.