Top Vacation Homes in Caribbean in 2026

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A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

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Top Cities in Caribbean

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

Punta Cana

A beach with clear turquoise water, a sandy shore, and a city skyline with tall buildings including a Marriott hotel.

San Juan

A cruise ship docked at a port with a clear blue sea and a small island in the background.

Nassau

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.

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a microwave.

A modern kitchen with stainless steel appliances, a microwave, and a coffee maker.

1. 1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear

3.5 star property

Santurce

9.2 out of 10, Wonderful, (195 reviews)

9.2/10

Wonderful

(195 reviews)

"Amazing stay"

Stanley

The price is HK$790

HK$790

HK$1,016 total

includes taxes & fees

2 Nov - 3 Nov

1120 Vieques by Stay with Bear

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.

A hotel room with a large bed, two wall-mounted lamps, a framed artwork, and a view of greenery through a sliding door.

A narrow pathway leading to a building entrance, flanked by white walls and greenery.

A spacious lobby with a checkered floor, a grey sofa, a black chair, and a wooden coffee table.

2. 150 Sol by Stay with Bear

150 Sol by Stay with Bear

3.0 star property

Old San Juan

8.6 out of 10, Excellent, (66 reviews)

8.6/10

Excellent

(66 reviews)

"Great location, easy access to property."

Jose

The price is HK$1,042

HK$1,042

HK$1,341 total

includes taxes & fees

25 Oct - 26 Oct

150 Sol by Stay with Bear

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

A modern kitchen with a dining area, a living room with a TV, and a large window.

A modern kitchen with a built-in oven and microwave, a dining area with a table and chairs, and a seating area with a sofa and armchairs.

A modern building with a blue exterior, a door labeled 'LAUNDRY,' and a small garden area with plants.

3. Miramar by PMI Puerto Rico

Miramar by PMI Puerto Rico

3.0 star property

Santurce

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"J"

Elisaul

The price is HK$666

HK$666

HK$1,823 total

includes taxes & fees

24 Oct - 25 Oct

Miramar by PMI Puerto Rico

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

A compact living space with a kitchenette, a dining area, and a sofa.

A modern living room with a grey sofa, a small wooden table, and a painting on the wall.

4. Residence Nokoshima

Residence Nokoshima

Fort-de-France

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"The apartment was very clean, a good price, but much smaller than the pictures make it look."

Karen

Residence Nokoshima

A modern living room with a sofa, a coffee table, and wicker chairs.

A hotel room with a bed, a washing machine, and a small plant.

A bedroom with a bed, a desk, a chair, a wardrobe, and a window with a view.

A swimming pool with a stone wall and a black fence.

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

5BR Private Pool Sleeps 10 Walk to Ocean Park Beach

Santurce

The price is HK$3,722

HK$3,722

HK$7,196 total

includes taxes & fees

26 Oct - 27 Oct

5BR Private Pool Sleeps 10 Walk to Ocean Park Beach

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

A modern kitchen with white cabinetry, a central island, and a staircase leading to an upper level.

A living room with a sofa, coffee table, and a view of the kitchen.

A two-story house with a central entrance and a small porch, surrounded by palm trees and a view of the ocean.

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

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

Providenciales

9.4 out of 10, Exceptional, (39 reviews)

9.4/10

Exceptional

(39 reviews)

"Beautiful view, comfortable breezy patio, great pool."

Vivian T.

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

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

A modern kitchen with white cabinets, a built-in oven, and a large island with seating. There is a dining area with a table and chairs, and a large mirror on the wall.

A modern bedroom with a large bed, bedside lamps, and a view through a sliding glass door.

A modern kitchen with white cabinets, a dining area with a round table and patterned chairs, and a large window with a view of the outdoors.

7. NÔA curacao

NÔA curacao

4.0 star property

Saliña

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"Beds were comfortable, a lot of kitchen utensils so cooking was easy there. Great location. Nice outdoor sitting area. You don't have a lot of privacy though."

Stephanie

NÔA curacao

A beach with clear turquoise waters, a sandy shore, and dense tropical vegetation.

A hotel hallway with a dark wooden door, a glass door, and a tiled floor.

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

A nighttime outdoor area with a swimming pool, potted plants, and a fenced area.

8. New pool and generator

New pool and generator

Boquerón

9.2 out of 10, Wonderful, (91 reviews)

9.2/10

Wonderful

(91 reviews)

"Excellent place! Very clean, close to the beach and quiet. We really enjoyed our stay!"

Celso A

New pool and generator

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

A bedroom with a tufted headboard, patterned bedding, a bedside table with a lamp, and a large mirror.

A living room with a beige sofa, a side table with a vase, and a colorful abstract painting on the wall.

A room with a sofa, chairs, a small table, and a decorative railing.

9. Villa mares.

Villa mares.

Sabana Abajo

9.2 out of 10, Wonderful, (16 reviews)

9.2/10

Wonderful

(16 reviews)

"Comfort, clean, good location"

Daisy

The price is HK$987

HK$987

HK$1,997 total

includes taxes & fees

30 Oct - 31 Oct

Villa mares.

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

A modern kitchen with stainless steel appliances, a built-in microwave, and a coffee maker.

A bathroom with a glass shower enclosure, a black toilet, a white sink with a black cabinet, and a marble-patterned wall.

A living room with a dark blue sofa, two round tables, and a decorative sign on the wall.

10. Home away II

Home away II

Cangrejo Arriba

9.2 out of 10, Wonderful, (35 reviews)

9.2/10

Wonderful

(35 reviews)

"Clean"

Damian

The price is HK$776

HK$776

HK$1,739 total

includes taxes & fees

29 Oct - 30 Oct

Home away II

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

A covered outdoor dining area with a ceiling fan, a table with chairs, and a view of palm trees.

A spacious dining area with a high ceiling and natural light, featuring a long table with chairs and a view of greenery outside.

A beach scene with palm trees and a rainbow over the ocean.

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

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

Zarzal

9.6 out of 10, Exceptional, (16 reviews)

9.6/10

Exceptional

(16 reviews)

"Wonderful property, great host. Our family truly enjoyed our stay."

Carly M.

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

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

A rectangular pool with clear blue water, surrounded by a brick wall and a metal fence.

A bedroom with a bed, a 'WELCOME' sign, a potted plant, and a view through a door with curtains.

A spacious kitchen with wooden cabinets, a large island, and a stone-patterned floor.

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

Bright, big, pool, 5 min 2 beach

Isla Verde

9.8 out of 10, Exceptional, (19 reviews)

9.8/10

Exceptional

(19 reviews)

"Perfect location and stay"

Chris L.

Bright, big, pool, 5 min 2 beach

A beach with palm trees, boats, and a distant cityscape.

A wooden table with plates and cutlery, a black chair, and lush greenery in the background.

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

A swimming pool with a wooden deck and surrounding tropical plants.

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

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

Les Trois-Îlets

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"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.

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

A modern living room with a glass coffee table, a potted plant, a black sofa, and a small side table.

A living room with a sofa, a dining table, and a TV.

A dining area with a table, chairs, a hanging light fixture, a door, and a wall-mounted air conditioner.

A round wooden table with a potted plant, a white picket fence, and a white door in the background.

14. Your retreat—close to the airport and everything you need, with a jacuzzi

Your retreat—close to the airport and everything you need, with a jacuzzi

Sabana Abajo

The price is HK$1,097

HK$1,097

HK$2,214 total

includes taxes & fees

23 Nov - 24 Nov

Your retreat—close to the airport and everything you need, with a jacuzzi

A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

A room with large windows, a stone wall, and a seating area with a sofa and chairs.

A building entrance with a black door, a set of stone steps, and a blue wheelchair.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a marble countertop.

15. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

Sunset Hideaway Suite - Oceanview/central to Cruz Bay

St John

9.8 out of 10, Exceptional, (20 reviews)

9.8/10

Exceptional

(20 reviews)

"Clean and spacious! Great location, proximity to Cruz Bay!"

Laina M.

The price is HK$1,873

HK$1,873

HK$3,244 total

includes taxes & fees

28 Oct - 29 Oct

Sunset Hideaway Suite - Oceanview/central to Cruz Bay

A covered outdoor seating area with a view of the ocean, a pool, and lounge chairs.

A barbecue grill with a view of a pool and ocean.

A modern kitchen with a black countertop and white cabinets, a dining area with chairs, and a view of the ocean through large windows.

A coastal property with a house, a swimming pool, and a beach.

16. Ocean Front Property With Pool. - George Town

Ocean Front Property With Pool. - George Town

Exuma

9.4 out of 10, Exceptional, (50 reviews)

9.4/10

Exceptional

(50 reviews)

"This house was perfect for us! The AC was cool, the beds were comfy, there was a washer and dryer, and the water jug connecting to the fridge was so convenient and provided ICE! The property manager was quick to respond and everything was exactly as pictured. Had a great stay and would highly recommend!"

Amber R.

Ocean Front Property With Pool. - George Town

A beach view with palm trees and a white fence leading to the sand.

A beachfront property with a swimming pool, a tennis court, and a view of the ocean.

A bedroom with a bed, curtains, and a view of the outdoors.

A coastal scene with palm trees and a view of the sea.

17. On the beach, a private pool, a house all to yourself.

On the beach, a private pool, a house all to yourself.

Bravos de Boston

9.8 out of 10, Exceptional, (210 reviews)

9.8/10

Exceptional

(210 reviews)

"Our extended family stayed here the 2nd week and enjoyed this Cottage even more than we did if that is possible!!!! What a slice of island heavenSweet lifetime memories made."

Susan R.

On the beach, a private pool, a house all to yourself.

A modern outdoor seating area with two blue wicker chairs, a small round table, and a potted plant.

A modern kitchen with a central island, a dining area with a round table, and a living room with a sofa and a coffee table.

A modern entrance with a wooden door, a small potted plant, and a tiled floor.

A swimming pool with a palm tree planter in the center, surrounded by a white fence and various plants.

18. Luxurious and Beautiful Isla Verde Beach house with private pool

Luxurious and Beautiful Isla Verde Beach house with private pool

Isla Verde

9.6 out of 10, Exceptional, (86 reviews)

9.6/10

Exceptional

(86 reviews)

"We loved the location and the house amenities. There are power and water struggles in San Juan, but the house had a generator and cistern."

Jeannie W.

Luxurious and Beautiful Isla Verde Beach house with private pool

A beach with clear turquoise water, a sandy shore, and wooden deck chairs under blue umbrellas.

A palm tree with coconuts, a white fence, and a gravel path.

A swimming pool with a pergola, lounge chairs, and a covered seating area.

19. Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

Grace Bay

10.0 out of 10, Exceptional, (71 reviews)

10/10

Exceptional

(71 reviews)

"It was a great place to stay. It was very clean and had all the amenities that we needed. Loved to pool. Location was great and parking was available."

Kellie C.

Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

A concrete pathway flanked by dense tropical foliage, leading through a lush garden area.

A kitchen with a central island, a dining area with a table and chairs, and a living area with a sofa and a window.

A swimming pool with lounge chairs and a canopy.

A dining area with a table set for four, a ceiling fan, and a view of the kitchen and outdoor area.

20. Private PoolFull SolarSecluded Rainforest Setting1 Mile from PR320 From SJU

Private Pool*Full Solar*Secluded Rainforest Setting*1 Mile from PR3*20 From SJU

Rio Grande

10.0 out of 10, Exceptional, (171 reviews)

10/10

Exceptional

(171 reviews)

"Our stay was remarkable and enjoyed it so much we are looking forward to coming back, the host is friendly, the house clean and cool, and the dogs are missed. We will definitely book another stay here"

Cheryl W.

Private Pool*Full Solar*Secluded Rainforest Setting*1 Mile from PR3*20 From SJU

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Caribbean Hotel Reviews

Hotel Rumbao, a Tribute Portfolio Hotel

10/10 Excellent

"2nd stay this year. Excellent location and staff is amazing!"

Peter S 1-night trip

Posted 1 hour ago

Hotel Rumbao, a Tribute Portfolio Hotel

Hilton Aruba Caribbean Resort and Casino

8/10 Good

"The beachfront is the best on the island. Stay in Tower 2 if you want to be closer to the Casino and Laguna restaurant for breakfast. Stay in Tower 1 if you want the standard of room you'd expect."

Paulette 3-night trip

Posted 6 hours ago

Hilton Aruba Caribbean Resort and Casino

The Royal at Atlantis

10/10 Excellent

"everything was perfect, I think the breakfast buffet prices are way too high compared to the rest"

Maud 5-night trip

Posted 7 hours ago

The Royal at Atlantis

Sheraton Santo Domingo Hotel

10/10 Excellent

"The room was neat and kept organized, and every single detail needed when we are away from home was provided. The staff was very professional and always willing to accommodate our needs. We had a great time while away from home and I recommend it to anybody that wants to have an easy and pleasant vacation."

Margarita 4-night trip

Posted 1 day ago

Sheraton Santo Domingo Hotel

Comfort Suites Paradise Island

10/10 Excellent

"Very helpful polite staff"

Darcy 6-night trip

Posted 1 day ago

Comfort Suites Paradise Island

The Reef at Atlantis

10/10 Excellent

"This place was wonderful. Highly recommend!"

BEATRIZ Eugenia 3-night trip

Posted 2 days ago

The Reef at Atlantis

Renaissance Wind Creek Curacao Resort

10/10 Excellent

"!"

Timothy 4-night trip

Posted 2 days ago

Renaissance Wind Creek Curacao Resort

Renaissance Wind Creek Aruba Resort

10/10 Excellent

"Loved all the details that went into the cabana on flamingo island. Everything was perfect!"

Danielle 2-night trip

Posted 2 days ago

Renaissance Wind Creek Aruba Resort

The Coral at Atlantis

10/10 Excellent

"100% recommend this trip and hotel! Everything went smoothly"

Daphne 6-night trip

Posted 3 days ago

The Coral at Atlantis

Find out more about Caribbean

Caribbean Vacation Homes information

Number of reviews	637
Accommodation	10966 Vacation Homes
Lowest Price	HK$1,016
Highest Price	HK$7,196

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Montego Bay Holidays
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Car hire San Juan

Vacation Homes in Caribbean

Check prices for these dates

Top Cities in Caribbean

Punta Cana

Our top choices for Caribbean holiday homes

1. 1120 Vieques by Stay with Bear

2. 150 Sol by Stay with Bear

3. Miramar by PMI Puerto Rico

4. Residence Nokoshima

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

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

7. NÔA curacao

8. New pool and generator

9. Villa mares.

10. Home away II

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

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

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

14. Your retreat—close to the airport and everything you need, with a jacuzzi

15. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

16. Ocean Front Property With Pool. - George Town

17. On the beach, a private pool, a house all to yourself.

18. Luxurious and Beautiful Isla Verde Beach house with private pool

19. Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

20. Private Pool*Full Solar*Secluded Rainforest Setting*1 Mile from PR3*20 From SJU

Find holiday rentals that suit your style

Top Caribbean Hotel Reviews

Hotel Rumbao, a Tribute Portfolio Hotel

Find out more about Caribbean

Caribbean Vacation Homes information

Explore a world of travel with Expedia

20. Private PoolFull SolarSecluded Rainforest Setting1 Mile from PR320 From SJU