Top Vacation Homes in Caribbean in 2026

Check prices for these dates

In two weeks

20 Nov - 22 Nov

In two months

1 Jan - 3 Jan

In three months

29 Jan - 31 Jan

In four months

26 Feb - 28 Feb

Top Cities in Caribbean

A marina with a white boat named 'Achina' docked, surrounded by palm trees and a building with a green roof.

Our top choices for Caribbean holiday homes

A modern bedroom with a large bed, bedside tables with lamps, a wardrobe, and an air conditioning unit.

1. 1120 Vieques by Stay with Bear

Santurce

Paulina

HK$1,389 total

includes taxes & fees

17 Nov - 18 Nov

A spacious dining area with a long wooden table and four black chairs, a large green plant, and a view of a white building with arches.

2. 150 Sol by Stay with Bear

Old San Juan

Jose

HK$1,403 total

includes taxes & fees

3 Nov - 4 Nov

A modern interior with a large window, a potted plant, and a door leading outside.

3. Miramar by PMI Puerto Rico

Santurce

Anthony

HK$1,825 total

includes taxes & fees

10 Nov - 11 Nov

A compact kitchen with a microwave, sink, and washing machine. There is a small dining area with stools and a table.

4. Residence Nokoshima

Fort-de-France

Karen

A modern living room with a sofa, chairs, and a coffee table. There is a view of a swimming pool through the glass door.

5. 5BR Private Pool Sleeps 10 Walk to Ocean Park Beach

Santurce

Carl C.

HK$6,767 total

includes taxes & fees

3 Nov - 4 Nov

A clear blue pool with lounge chairs and umbrellas, surrounded by tropical vegetation and a view of the ocean.

6. Escape to Exhale at a modern style villa with breathtaking views of chalk sound

Providenciales

Vivian T.

A swimming pool with lounge chairs and palm trees, surrounded by buildings and a clear sky.

7. NÔA curacao

Saliña

Stephanie

An outdoor patio with a wooden roof, wicker furniture, and a bar area.

8. New pool and generator

Boquerón

Celso A

A room with a sofa, a chair, a small table, and a view of the outside.

9. Villa mares.

Sabana Abajo

Daisy

HK$1,791 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with a central island, stainless steel appliances, and two bar stools.

10. Home away II

Cangrejo Arriba

Damian

HK$1,639 total

includes taxes & fees

3 Nov - 4 Nov

A poolside area with a clear pool, white lounge chairs, and a covered patio with steps leading to the pool.

11. 2bedroom beach front house in soothing Río Grande with AC and salt swimming pool

Zarzal

Carly M.

A spacious living area with a dining table, sofas, and a chandelier.

12. Bright, big, pool, 5 min 2 beach

Isla Verde

Chris L.

HK$6,215 total

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a bed, a hanging plant, a shelf with jars, and a unique light fixture.

13. Detached lodge on the property with a swimming pool (shared) located 5 minutes from the beach

Les Trois-Îlets

"We stayed at this property for seven nights, and it was absolutely magical. The sunsets and sounds of the tropical forest were amazing. Phillips and his wife were so very welcoming and showed us a map of what to do and where we should visit on the island. The kitchen area has everything you’d need to prepare small meals and enjoy them from your private deck. The location is perfect for setting out to explore the island and its stunning beaches. I would absolutely recommend staying here, and hope...

Samantha G.