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

Holiday Homes in Caribbean

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Caribbean

Our top choices for Caribbean holiday homes

1. 1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.2 out of 10, Wonderful, (158 reviews)
"Easy check in process and good location."
United States
Joshua Thomas
The price is €85
includes taxes & fees
25 Aug - 26 Aug
1120 Vieques by Stay with Bear

2. Alto Vista Hills

Alto Vista Hills
3.5 star property
Noord
8.4 out of 10, Very good, (9 reviews)
"The location was perfect. All places of interest were within reasonable distance and travel times. Quiet neighborhood. The room was comfortable. Communicating with Amir was easy, replying within minutes. Was able to meet him and speak face to face. Only few suggestions regarding place Mattress Covers AC filters ( clean more often) If possible a coin operated laundry room I would certainly stay here again!!"
United States
Ricardo
Alto Vista Hills

3. 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, (59 reviews)
"First time to Old San Juan, and the location was ideal."
Canada
George Todd
The price is €158
includes taxes & fees
4 Aug - 5 Aug
150 Sol by Stay with Bear

4. Ocean Front-Great Location

Ocean Front-Great Location
Playa Fortuna
9.8 out of 10, Exceptional, (64 reviews)
"Wonderful apartment and great beach. Close to everything. Highly recommend;"
United States
Heidi
The price is €222
includes taxes & fees
19 Aug - 20 Aug
Ocean Front-Great Location

5. Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!

Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!
Ramsey
10.0 out of 10, Exceptional, (150 reviews)
"The location on the island and the views were amazing. The house was spotless when we checked in and was fully stocked with everything you need for a Beach House!"
United States
Glen M.
Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!

6. Comfy and cozy mini house sitting on a beautiful 1500 meter lot. Great location!

Comfy and cozy mini house sitting on a beautiful 1500 meter lot. Great location!
Aguadilla
8.8 out of 10, Excellent, (51 reviews)
"Excellent experience. The host was very nice. Love the location. Relax"
United States
Rebeca
Comfy and cozy mini house sitting on a beautiful 1500 meter lot. Great location!

7. Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
St John
9.6 out of 10, Exceptional, (37 reviews)
"We had everything we needed to cook any meal. The rooms were clean and comfortable. We really loved the outdoor showers! Parking was a non-issue. The pool and view were amazing! Honestly, the perfect space and location for two couples. "
United States
Stephanie W.
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

8. One minute walk to the beach!

One minute walk to the beach!
Mata de Plátano
9.2 out of 10, Wonderful, (60 reviews)
"Parking spot included, walking distance to the beach, really nice room."
United States
Manuel
One minute walk to the beach!

9. Villa mares.

Villa mares.
Sabana Abajo
9.8 out of 10, Exceptional, (7 reviews)
"Exelente limpieza la propiedad muy acogedora no problemas área muy callada i segura"
United States
Francisco
Villa mares.

10. Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.

Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.
Zarzal
10.0 out of 10, Exceptional, (108 reviews)
"We had a fantastic stay! Princess is a wonderful host. Our entire family had a great vacation, would love to stay here again and again. "
United States
Anonymous traveller
Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.

11. Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go

Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
Isla Verde
9.0 out of 10, Wonderful, (48 reviews)
"Quiet closer to airport and restaurants are walkable distance."
United States
Naveen
The price is €116
includes taxes & fees
2 Aug - 3 Aug
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go

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

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay if you are visiting St. John! Very clean, great view from the patio and 5 min from downtown area. "
United States
Christopher
The price is €366
includes taxes & fees
8 Aug - 9 Aug
Sunset Hideaway Suite - Oceanview/central to Cruz Bay

13. The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub

The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub
Exuma
10.0 out of 10, Exceptional, (127 reviews)
"Truly an unforgettable week! The property was incredible, and Heather went above and beyond to make our stay perfect. From thoughtful recommendations to a seamless check-in—and even coordinating baby rentals and groceries—everything was handled flawlessly.I can’t say enough wonderful things about this property… though part of me wants to keep it a hidden gem!Heather, thank you again for an amazing week. We’ll see you next March!"
United States
Melissa B.
The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub

14. Blue House Joyuda

Blue House Joyuda
3.5 star property
Cabo Rojo
9.4 out of 10, Exceptional, (44 reviews)
"Host was always very polite and responsive."
United States
Myrna
The price is €120
includes taxes & fees
18 Aug - 19 Aug
Blue House Joyuda

15. luxurious home with 360 degree ocean views

luxurious home with 360 degree ocean views
Treasure Cay
10.0 out of 10, Exceptional, (111 reviews)
"Truly an excellent house and location. Misty was very responsive and excellent to work with. We were very satisfied with our stay and cannot wait to return. Highly recommend."
United States
Tim D.
luxurious home with 360 degree ocean views

16. Extra Large Two Story Oceanfront Home | 10 mins from Rincón & Aguadilla | ON THE BEACH SLEEPS 24 PLUS

Extra Large Two Story Oceanfront Home | 10 mins from Rincón & Aguadilla | ON THE BEACH SLEEPS 24 PLUS
Bo Espinar Aguada
Extra Large Two Story Oceanfront Home | 10 mins from Rincón & Aguadilla | ON THE BEACH SLEEPS 24 PLUS

17. Casita Chiquita #1

Casita Chiquita #1
Aguadilla
9.0 out of 10, Wonderful, (46 reviews)
"The house was perfect. It’s a great place to stay if you have an early flight, as it’s conveniently located close to the airport."
United States
Maria
Casita Chiquita #1

18. Coco Palms - private beach Oasis on Coco Bay just steps from Sea Turtle preserve

Coco Palms - private beach Oasis on Coco Bay just steps from Sea Turtle preserve
North Abaco
9.4 out of 10, Exceptional, (3 reviews)
"We loved our stay at Plum Crazy! We felt the hosts went above and beyond with their communication, information and recommendations, and hospitality. The option to have groceries stocked upon arrival was a game changer and allowed us to step right into vacation mode. The house itself is beautiful, has a great location and was very clean. The sunset views were spectacular. Thanks for a great stay!"
United States
Jade C.
Coco Palms - private beach Oasis on Coco Bay just steps from Sea Turtle preserve

19. The Beach Pad

The Beach Pad
3.0 star property
Rincon
9.8 out of 10, Exceptional, (79 reviews)
"Fantastic place to stay. Clean, easy check in, and the most beautiful drive to and from Rincon. Highly recommend staying here."
United States
Maria Elizabeth
The Beach Pad

20. NÔA curacao

NÔA curacao
4.0 star property
Saliña
9.8 out of 10, Exceptional, (6 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."
United States
Stephanie
NÔA curacao
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Caribbean Hotel Reviews

Find out more about Caribbean

Caribbean Holiday Homes information

Number of reviews
1,117
Accommodation
11230 Holiday Homes
Lowest Price
€85
Highest Price
€366

Explore a world of travel with Expedia