
Caribbean Islands Vacations from ¥76,903
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Caribbean Islands Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort
Save 100% on your flight
per person
Sep 15 - Sep 19
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9.2/10 Wonderful! (1,220 reviews)
This was my 3rd stay there. It was as marvelous as my 1st and 2nd. The beach was wonderful and breakfast was great.
Reviewed on Aug 13, 2025

Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
per person
Sep 15 - Sep 19
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9.2/10 Wonderful! (949 reviews)
The thing that stands out the most was this is not a place for anyone with mobility issues. There can be a lot of stairs to climb depending on where in the complex you’re going. The buildings themselves make you feel like you have transported to Europe. The pool was perfect and our daughter loved the diving board and slide. The furnishings/appliances are kinda at the point of needing replaced but they met our needs. The air worked well which was a huge plus. We had a few minor issues at first but management sent immediate staff to investigate and address. If we had a real negative is I wish the balcony had nicer furniture such as chaise lounge chairs and a smaller table so you could really sit out and relax and enjoy the quiet. Other than that we would definitely consider staying here again. It is in an area with less activity but that is why we chose it but you definitely want a car.
Reviewed on Aug 13, 2025

The Morgan Resort Spa Village
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
9/10 Wonderful! (1,793 reviews)
The receptionist (morning shift) had a terrible mood, unpleasant and not kind at all. However, the ladies from the SALT RESTAURANT were extremely kind and lovely. Ravi was fantastic too, great member staff, super happy and kind.
Reviewed on Aug 14, 2025


Royal Islander Resort La Plage
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
8.6/10 Excellent! (302 reviews)
We have found that booking through 3rd party that we are given the most undesirable rooms. We asked for another room after waiting for an hour and a half for a manager to respond, we ended up keeping the room assigned to us with a promise of being moved first thing the next morning. I was told that if I withdraw an earlier review on our previous stay by Ms Lena the manager, the room was not available at 2:00pm, we stayed in our assigned room. This resort is a part of RCI vacation rentals.
Reviewed on Aug 9, 2025
Where to stay in Caribbean Islands
Find the best Caribbean Islands areas and neighborhoods for the activities you enjoy most. Learn more about Caribbean Islands

Palm Beach
Enjoy yourself at this white-sand Caribbean beach that combines incredible underwater sights and tangerine sunsets with a youthful nightlife.
Find the Best Caribbean Islands Vacation Packages
Caribbean Islands Hotel Deals

Grand Hyatt Baha Mar
One Baha Mar Boulevard, Nassau, New Providence
Fully refundableReserve now, pay when you stay
The price is ¥35,193 per night from Aug 27 to Aug 28
¥35,193
¥57,776 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (4,358 reviews)
"I like that the property was clean. The employees were courteous and helpful"
Reviewed on Aug 13, 2025

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro, Higuey, Punta Cana, La Altagracia
Fully refundableReserve now, pay when you stay
The price is ¥49,467 per night from Sep 1 to Sep 2
¥49,467
¥63,317 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (5,521 reviews)
"The Lopesan resort was beautiful! The rooms were spacious, clean and comfortable. The staff was extremely friendly and welcoming, which made the stay even better. I wish we would have been able to try more restaurants during our stay but they fill up quickly, I highly recommend as soon as you receive ..."
Reviewed on Aug 12, 2025

Hotel Riu Republica - Adults only - All Inclusive
Playa Arena Gorda, Punta Cana
7.2/10 Good! (4,731 reviews)
"Overall pretty good."
Reviewed on Aug 14, 2025
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.
Discover the most popular places to visit in Caribbean Islands

Eagle Beach
Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.

Punta Cana Beach
Nothing says vacation like spending a lazy day at Punta Cana Beach, a popular beach in Punta Cana. Amble around this romantic area's seaside and enjoy its lively bars.

Luquillo Beach
Sample local street food or doze under a palm tree on this picturesque stretch of coast.
Frequently asked questions
Other vacations you might like
Expedia's Latest Trends
Hotels
- Asante inn - Hostel
- Cheap Hotels in Kobe
- Pet-friendly Hotels in Ibaraki Prefecture
- Pet-friendly Hotels in Shibuya
- Edsa Shangri-La, Manila
- Hotels in Montreal
- Hotels near Tenkubashi Station
- lyf Bugis Singapore
- Toyoko Inn Tokyo Seibu Ikebukuro Line Higashi Kurume Station Nishi
- Hotel Bali An Resort Shinjuku Island - Adults only
Flights
- Flights from Narita (NRT) to Shannan (LXA)
- Flights from Osaka (KIX) to Tel Aviv (TLV)
- Flights from Haneda
- Flights from Sacramento (SMF) to Narita (NRT)
- Flights from Kobe (ITM) to Winnipeg (YWG)
- Flights from Bangkok (BKK) to Fukuoka (FUK)
- Flights from Manila (MNL) to El Nido (ENI)
- Flights from Takamatsu
- Flights to Tunisia
- Flights to Puerto Rico Island
Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.