Vacation Homes in Caribbean

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In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Caribbean vacation homes

Apartment, 2 Bedrooms, Corner | Private spa tub

1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.2 out of 10, Wonderful, (134 reviews)
"This was a great place to stay at."
United States
Jocelyn
The price is ￥14,679
￥16,000 total
includes taxes & fees
Jun 24 - Jun 25
1120 Vieques by Stay with Bear
Exterior

Sugar Apple Bed & Breakfast

Sugar Apple Bed & Breakfast
3.5 star property
Christiansted Historic District
9.2 out of 10, Wonderful, (79 reviews)
"Clean room, nice bathroom, comfortable bed"
United States
DEBORAH
Sugar Apple Bed & Breakfast
Front of property

The Suite Life

The Suite Life
4.0 star property
Rokers Point
7.6 out of 10, Good, (14 reviews)
"The view and easy access to the beach was the highlight. The property manager was very accomodating. "
United States
Antonia
The price is ￥46,771
￥72,583 total
includes taxes & fees
Jun 5 - Jun 6
The Suite Life
Smart TV

Villa mares.

Villa mares.
Sabana Abajo
10.0 out of 10, Exceptional, (3 reviews)
"My kids loved the house. We are in our home town and they are asking when are we gonna go back to our new house."
United States
Alice H.
The price is ￥15,830
￥35,638 total
includes taxes & fees
Jun 13 - Jun 14
Villa mares.
Beach

3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.

3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.
Grand Cayman
10.0 out of 10, Exceptional, (37 reviews)
"Really nice place, the pictures are great but really don’t do the property justice, it was an amazing week for us. Everything about the property was excellent. Owner checked in on us via email and was an excellent host. All I can say is if you are wanting to stay in the Rum Point area you have to consider this place, it is amazing. "
United States
Dwight K.
3 Bedroom Oceanfront Villa, Private Pool, Sandy Beach, Near Famous Rum Point.
Premium Apartment, 2 Bedrooms | Terrace/patio

Playa Nueva Romana

Playa Nueva Romana
3.5 star property
Ramón Santana
9.0 out of 10, Wonderful, (47 reviews)
"Amazing stay! Clean, staff was so nice and helpful"
United States
Antonio
Playa Nueva Romana
Interior

Luxury House in Old San Juan

Luxury House in Old San Juan
Old San Juan
9.4 out of 10, Exceptional, (40 reviews)
"Yes the host was very friendly and it was a very nice place to stay."
United States
sean m.
The price is ￥78,863
￥119,841 total
includes taxes & fees
Jun 9 - Jun 10
Luxury House in Old San Juan
Outdoor pool

Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End

Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End
St. John
9.6 out of 10, Exceptional, (119 reviews)
"Had everything we needed for a relaxing vacation! Pool was a great bonus & the views were unbelievable! Definitely off the beaten path…if you’re looking for a laid back, quiet place to stay, this is it!"
United States
Eric N.
Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End
Comfort House, 2 Bedrooms | Terrace/patio

Villa Serenity by the water

Villa Serenity by the water
3.5 star property
Cooper Jack Bay Settlement
8.6 out of 10, Excellent, (33 reviews)
"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 ￥32,380
￥52,434 total
includes taxes & fees
Jun 5 - Jun 6
Villa Serenity by the water
On the beach, sun loungers, beach towels

2BR Private Pool Villa • 3-Minute Walk to Grace Bay • Sleeps 4

2BR Private Pool Villa • 3-Minute Walk to Grace Bay • Sleeps 4
Grace Bay
10.0 out of 10, Exceptional, (63 reviews)
"Very easy check in and parking was great. Very close to the beach and the house itself was very clean. Really enjoyed the pool."
United States
Leslie L.
2BR Private Pool Villa • 3-Minute Walk to Grace Bay • Sleeps 4
Fridge, oven, stovetop, coffee/tea maker

Casita Chiquita #1

Casita Chiquita #1
Aguadilla
9.0 out of 10, Wonderful, (42 reviews)
"Great stay for the value. "
United States
Dariya
The price is ￥15,670
￥19,965 total
includes taxes & fees
Jun 18 - Jun 19
Casita Chiquita #1
Balcony view

The Beach Pad

The Beach Pad
3.0 star property
Rincon
9.8 out of 10, Exceptional, (70 reviews)
"Perfectly situated near beach and restaurants."
United States
Craig
The Beach Pad
On the beach, sun loungers, beach towels

OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!

OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
Yabucoa
10.0 out of 10, Exceptional, (166 reviews)
"Wonderful location and views. The place was very clean. Amenities such as pool toys, chairs etc. were great. Elizabeth got back to me on my questions very quickly."
United States
DennisTheDog100
OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
Outdoor dining

150 Sol by Stay with Bear

150 Sol by Stay with Bear
3.0 star property
Old San Juan
8.4 out of 10, Very Good, (52 reviews)
"Staff was friendly"
Canada
Jair Mario
The price is ￥23,985
￥30,848 total
includes taxes & fees
Jun 7 - Jun 8
150 Sol by Stay with Bear
A heated pool

Salt Box: an Enchanting Historical Property with a Pool

Salt Box: an Enchanting Historical Property with a Pool
Dunmore
10.0 out of 10, Exceptional, (97 reviews)
"Host was very welcoming and the home was just so full of character and the yard was spectacular. "
United States
Sarah S.
Salt Box: an Enchanting Historical Property with a Pool
Property grounds

Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise
4.0 star property
North Side
9.6 out of 10, Exceptional, (40 reviews)
"Beautiful property!! Nice and clean and quiet! House was huge! Definitely will stay again!"
United States
Kimberly G
The price is ￥51,290
￥107,179 total
includes taxes & fees
Jun 15 - Jun 16
Cayman Luxury Rentals at Ocean Paradise
Fridge, oven, stovetop, coffee/tea maker

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, (45 reviews)
"The host and how kind and generous he was to us. "
United States
Brooklynn D.
The price is ￥15,670
￥19,965 total
includes taxes & fees
Jun 18 - Jun 19
Comfy and cozy mini house sitting on a beautiful 1500 meter lot. Great location!
Outdoor pool

Bamboo House: Charming Private Tropical Oasis in the Heart of the Village.

Bamboo House: Charming Private Tropical Oasis in the Heart of the Village.
Harbour Island
10.0 out of 10, Exceptional, (82 reviews)
"The house was perfect for a group of our size and conveniently located in town "
United States
Clark H.
Bamboo House: Charming Private Tropical Oasis in the Heart of the Village.
Living area

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
10.0 out of 10, Exceptional, (1 review)
"With a breathtaking view of Coco Bay, this home is very comfortable, newly renovated and furnished with everything you’ll need to enjoy your time on Green Turtle. The host went above and beyond to make sure all the logistics were coordinated and that everything flowed smoothly upon arrival. The best part, ten steps to the beautiful blue waters of Coco Bay! Looking forward to a return visit soon."
United States
B S.
Coco Palms - private beach Oasis on Coco Bay just steps from Sea Turtle preserve
Outdoor dining

Ocean Front-Great Location

Ocean Front-Great Location
Playa Fortuna
9.8 out of 10, Exceptional, (54 reviews)
"This unit was very nicely laid out and updated. The kitchen and bathrooms were well stocked with lots of essentials. The view from the big balcony was amazing."
United States
Joni
The price is ￥17,909
￥39,894 total
includes taxes & fees
Jun 20 - Jun 21
Ocean Front-Great Location
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

Hotel Rumbao, a Tribute Portfolio Hotel

10/10 Excellent
"Location of this property is excellent. Wouldn’t stay anywhere else. Shopping, food everything you need. There is even a Walgreens next to the hotel."
Sherryann 1-night trip
Posted 1 hour ago
Hotel Rumbao, a Tribute Portfolio Hotel

Find out more about Caribbean

Caribbean Vacation Homes information

Number of reviews
903
Accommodation
14020 Vacation Homes
Lowest Price
￥16,000
Highest Price
￥119,841