Holiday Homes in Caribbean

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In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Top Cities in Caribbean

Willemstad which includes swimming, a sandy beach and rugged coastline
Holiday HomesHoliday Homes

Willemstad

Willemstad

Our top choices for Caribbean holiday homes

Outdoor dining
150 Sol by Stay with Bear

Holiday Home in Old San Juan

150 Sol by Stay with Bear
3.0 star property
8.4 out of 10, Very good, (8)
"Great experience, on point customer service, will definitely recommend!!"
United States
Efrain
The price is €135
includes taxes & fees
21 Dec - 22 Dec
150 Sol by Stay with Bear
Apartment, 1 Queen Bed, Non Smoking, Patio | Private kitchen
1120 Vieques by Stay with Bear

Holiday Home in Santurce

1120 Vieques by Stay with Bear
3.5 star property
9.6 out of 10, Exceptional, (79)
"Room was clean. Good Air condition. Easy instructions for check in . Would come back :) "
United States
Sylvie
1120 Vieques by Stay with Bear
Terrace/patio
Sugar Apple Bed & Breakfast

Holiday Home in Christiansted Historic District

Sugar Apple Bed & Breakfast
3.5 star property
9.4 out of 10, Exceptional, (65)
"Very nice cozy place. Excellent to have some rest and enjoy the island."
United States
Joann
Sugar Apple Bed & Breakfast
Private beach, white sand, free beach cabanas, sun-loungers
Playa Nueva Romana

Holiday Home in Ramón Santana

Playa Nueva Romana
3.5 star property
9.0 out of 10, Wonderful, (30)
"Room size and location. "
United States
Hipolito
Playa Nueva Romana
Exclusive Tent, River View
Casa Parcha

Holiday Home in Naguabo

Casa Parcha
3.5 star property
10.0 out of 10, Exceptional, (33)
"This retreat was exactly what I was looking for. It offered a quiet stay surrounded by nature. I gave me a chance to reconnect with myself and to enjoy the glorious sounds of the coqui. The communication was top notch. Everyone I encountered was extremely friendly and available to assists with all my needs. This is definitely a gem. "
United States
Ileana
The price is €168
includes taxes & fees
31 Dec - 1 Jan 2026
Casa Parcha
Balcony view
The Beach Pad

Holiday Home in Rincon

The Beach Pad
3.0 star property
9.8 out of 10, Exceptional, (62)
"I had the best night sleep that I haven’t had for a really long time! Owner communicated well. Would definitely recommend 🙌"
United States
Evelyn
The Beach Pad
Comfort House, 2 Bedrooms | Private kitchen
Villa Serenity by the water

Holiday Home in Discovery Bay

Villa Serenity by the water
3.5 star property
8.6 out of 10, Excellent, (32)
"The room was very clean, spacious and the staff Sherlett was amazing and helped out whenever needed and responded quickly. Even with some construction going on the room was very peaceful I will definitely stay again "
United States
alondra
The price is €210
includes taxes & fees
4 Jan - 5 Jan 2026
Villa Serenity by the water
Beach
Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.

Holiday Home in governors harbour

Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.
10.0 out of 10, Exceptional, (125)
"This was our second time staying at Sea Shanty. The home is in a great location and has everything we need for our stay. "
United States
Stephanie B.
The price is €269
includes taxes & fees
19 Dec - 20 Dec
Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.
Terrace/patio
Gordon's Island Art Loft

Holiday Home in Charlotte Amalie

Gordon's Island Art Loft
9.6 out of 10, Exceptional, (37)
"The location is a bit rough to get to with the roads, but overall, the place is beautiful with a gorgeous view."
United States
Porsha D.
Gordon's Island Art Loft
Property grounds
Charming “Poker Face” has Phenomenal Views & Dock

Holiday Home in Elbow Cay

Charming “Poker Face” has Phenomenal Views & Dock
10.0 out of 10, Exceptional, (54)
"Perfect little house! We were there for our honeymoon and everything was great! Centrally located on the island and easy golf cart ride to dinner and the beach! Beautiful sunset views from the porch! "
United States
Beth N.
Charming “Poker Face” has Phenomenal Views & Dock
Outdoor pool, a heated pool
La Posada Mountain Retreat - Exceptionally Stunning Views

Holiday Home in Utuado

La Posada Mountain Retreat - Exceptionally Stunning Views
10.0 out of 10, Exceptional, (76)
"Jose and Christine go above and beyond for the comfort of their guests. You feel 100% at home every time. We only had 4 days this time, but we thoroughly enjoyed every second. It’s a climb to the top of the mountain, to the house, but worth it. "
United States
Kelly D.
La Posada Mountain Retreat - Exceptionally Stunning Views
Pool
Ocean Front Property With Pool. - George Town

Holiday Home in Exuma

Ocean Front Property With Pool. - George Town
9.6 out of 10, Exceptional, (32)
"Phenomenal location, beautiful view!!!!! Having paddleboards and kayaks was fantastic- such a neat location with the sand bars right off the shoreline. Highly recommended house and location! "
United States
William C.
Ocean Front Property With Pool. - George Town
On the beach, beach towels
4-bedroom House with private Pool - walking distance to Baha Mar and Beach

Holiday Home in Cable Beach

4-bedroom House with private Pool - walking distance to Baha Mar and Beach
9.4 out of 10, Exceptional, (10)
"Newly renovated, clean and comfortable. Loved the outside area as well. Walkability to some restaurants and shops. "
United States
Tracy J.
4-bedroom House with private Pool - walking distance to Baha Mar and Beach
Terrace/patio
Sophisticated Beach Condo-Ocean View-Sapphire

Holiday Home in Smith Bay

Sophisticated Beach Condo-Ocean View-Sapphire
9.0 out of 10, Wonderful, (32)
"Me and my gf’s loved staying here! Best part was having close beach access! "
United States
Maria
The price is €287
includes taxes & fees
17 Jan - 18 Jan 2026
Sophisticated Beach Condo-Ocean View-Sapphire
Property grounds
Charming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking

Holiday Home in Barranquitas

Charming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking
2.0 star property
10.0 out of 10, Exceptional, (14)
"This was a very beautiful home the view was perfect "
United States
Dominique
Charming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking
Fridge, microwave, oven, coffee/tea maker
The charming 11 minutes from the baths of Coamo. To feel at home!!!

Holiday Home in Mariano Colon

The charming 11 minutes from the baths of Coamo. To feel at home!!!
9.2 out of 10, Wonderful, (11)
"This house was beautiful and felt like a home away from home. My family and I were extremely comfortable and enjoyed staying here. "
United States
Je B.
The charming 11 minutes from the baths of Coamo. To feel at home!!!
Smart TV
PLAYA AZUL1 2ND FLOOR BEACHFRONT LUX DESIGNER CONDO.

Holiday Home in Mata de Plátano

PLAYA AZUL1 2ND FLOOR BEACHFRONT LUX DESIGNER CONDO.
9.8 out of 10, Exceptional, (42)
"Great location. Great views. Beautiful beach. Great communication with host. A for the whole vacation. "
United States
Brent R.
PLAYA AZUL1 2ND FLOOR BEACHFRONT LUX DESIGNER CONDO.
Luxury Townhome, Villa 232D
Blue Luxury Properties

Holiday Home in Jolly Harbour

Blue Luxury Properties
4.0 star property
Blue Luxury Properties
Outdoor pool, a heated pool
The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub

Holiday Home in Exuma

The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub
10.0 out of 10, Exceptional, (117)
"Incredible modern home! Will most certainly be back! Great hosts and great location! "
United States
lauren h.
The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub
On the beach, sun-loungers
Casa Del Mar Beachfront House on quiet beach, surf out front, tidepools for kids

Holiday Home in Aguada

Casa Del Mar Beachfront House on quiet beach, surf out front, tidepools for kids
10.0 out of 10, Exceptional, (68)
"We loved our stay at Casa Del Mar! Clean, super comfortable, and equipped with everything we needed. The beach was amazing and we often had it to ourselves. Since we were there I'm the July heat, we were grateful for the AC. Highly recommend! Perfect accommodations for our family vacation."
United States
Heidi W.
Casa Del Mar Beachfront House on quiet beach, surf out front, tidepools for kids
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

La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

10/10 Excellent
"Amazing resort! Staff was very accommodating and friendly. All areas of the resort were exceptionally clean and there was plenty to do! We wouldn’t even have had to leave the resort if we didn’t want to! Would definitely stay again!"
Pamela Lynn 5-night trip
Posted 15 hours ago
La Concha Resort, Puerto Rico, Autograph Collection

Find out more about Caribbean

Caribbean Holiday Homes information

Number of reviews
920
Accommodation
13574 Holiday Homes
Lowest Price
€135
Highest Price
€287