Caribbean Islands Vacation Packages

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Your Caribbean Islands Vacation

Leave the planning up to us with a Caribbean Islands vacation package. With everything arranged before you jet off, the only thing you'll need to do is sit back, relax and enjoy this destination's countless delights. Begin your trip to Caribbean Islands by spending a few nights in Punta Cana, one of the best cities here. When you're ready to stop dreaming and start travelling, Expedia will help turn your Caribbean Islands vacation into a reality.

Top Caribbean Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,642, price is now CA $953 per person
CA $953
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (922 reviews)
The staff was excellent very attentive to your neefs

Reviewed on Aug. 20, 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $2,060, price is now CA $1,421 per person
CA $1,421
per person
Oct 17 - Oct 22
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.4/10 Exceptional! (587 reviews)
Love the area, grounds, beach and room. Food is amazing and the bartenders and waitstaff were always attentive to us and they remembered us from our last stay 2 years ago!! La Playa made our 7th wedding anniversary truly special. This is one of the best places to stay in St Martin. We can’t wait to come back!

Reviewed on Aug. 19, 2025

Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was CA $2,987, price is now CA $2,210 per person
CA $2,210
per person
Nov 1 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (464 reviews)
Nice having semi-private pool. All of the staff very friendly and helpful. Including at L'Astrolabe for breakfast and dinner.

Reviewed on Jun. 13, 2025

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $3,305, price is now CA $2,447 per person
CA $2,447
per person
Nov 1 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (1,810 reviews)
Great place ! The staff was amazing and I would stay here again !!

Reviewed on Aug. 24, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was CA $2,057, price is now CA $1,152 per person
CA $1,152
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Our stay was great. Had stayed here before almost 20 years ago and it was just as we remember it. They need to update equipment in the gym, and I thought the daily charge for the gym was a little silly. The pool and pool bar staff at the Villas were fantastic. They kept everything exceptionally clean. We would return and stay there again!

Reviewed on Aug. 25, 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 which includes a beach

Palm Beach

Enjoy yourself at this white-sand Caribbean beach that combines incredible underwater sights and tangerine sunsets with a youthful nightlife.

Find hotels in Palm Beach

Things to do in Caribbean Islands

The Caribbean Islands offer a perfect blend of culture-themed adventures and stunning beach getaways. Visitors can indulge in beach vacations, enjoy golf at scenic courses, and explore beachfront experiences. For the adventurous, there are thrilling underwater sports and excellent snorkeling spots, as well as exciting island adventures waiting to be discovered. Get ready to immerse yourself in the vibrant atmosphere and natural beauty of the Caribbean.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Best time to go to Caribbean Islands

The best time to visit Caribbean Islands depends on your weather preferences. The hottest average temperature around Caribbean Islands is in September, when weather is mostly sunny and rainfall is light rain. The coolest average temperature around Caribbean Islands is in November when weather is mostly sunny and rainfall is light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudiness
January79.3°F (26.3°C)No RainMostly Sunny
February78.8°F (26.0°C)No RainMostly Sunny
March79.2°F (26.200000000000003°C)No RainMostly Sunny
April80.1°F (26.700000000000003°C)Light RainMostly Sunny
May80.4°F (26.9°C)Light RainMostly Sunny
June81.7°F (27.6°C)Light RainMostly Sunny
July82.2°F (27.9°C)Light RainMostly Sunny
August82.8°F (28.200000000000003°C)Light RainMostly Sunny
September82.9°F (28.3°C)Light RainMostly Sunny
October82.6°F (28.1°C)Light RainMostly Sunny
November78.3°F (25.700000000000003°C)Light RainMostly Sunny
December79.5°F (26.4°C)No RainMostly Sunny

Tips to save on your trip to Caribbean Islands

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Caribbean Islands.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ready to book your vacation to Caribbean Islands?

 

Choose your dates

Caribbean Islands Hotel Deals

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
One Baha Mar Boulevard, Nassau, New Providence
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Aug 26 to Aug 27
CA $289
CA $493 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (4,375 reviews)
"Friendly staff and well kept property."

Reviewed on Aug. 21, 2025

Grand Hyatt Baha Mar
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

5 out of 5
Playas de Bavaro, Higuey, Punta Cana, La Altagracia
Fully refundableReserve now, pay when you stay
The price is CA $464 per night from Sep 1 to Sep 2
CA $464
CA $595 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (5,604 reviews)
"Amazing"

Reviewed on Aug. 24, 2025

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Hotel Riu Republica - Adults only - All Inclusive

Hotel Riu Republica - Adults only - All Inclusive

4 out of 5
Playa Arena Gorda, Punta Cana
7.2/10 Good! (4,776 reviews)
"Everything"

Reviewed on Aug. 22, 2025

Get rates
Hotel Riu Republica - Adults only - All Inclusive
See all 81,396 properties in Caribbean Islands
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Caribbean Islands

Eagle Beach showing a sandy beach

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.

Eagle Beach
Grace Bay Beach which includes a beach

Grace Bay Beach

Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.

Grace Bay Beach
Bavaro Beach

Bavaro Beach

Nothing says vacation like spending a lazy day at Bavaro Beach, a popular beach in Punta Cana. Discover the lively bars and entertainment choices in this relaxing area.

Bavaro Beach

Frequently asked questions

How much does a Caribbean Islands vacation package cost?
Perhaps much less than you think — from only CA $953, as a matter of fact! By combining hotels, flights and car rentals into your own custom-built vacation package, your getaway to Caribbean Islands is only clicks away.
How do I get a cheap travel package to Caribbean Islands?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Select a combination that best suits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotel options throughout the world, which lets you customize your Caribbean Islands adventure.
What are the top hotels in Caribbean Islands?
Check out Christopher Hotel and Le Sereno. They're top picks for lots of travelers to St. Barthelemy. If San Juan is on your itinerary, Costa Bahia Hotel Paseo Caribe and La Concha Renaissance San Juan Resort are two top-notch options.
How far in advance should I book my Caribbean Islands vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to departure dates. This is often the cheapest time to book. If circumstances have left you booking late, discount prices to Caribbean Islands sometimes become available in the weeks leading up to departure.
What does an Expedia Caribbean Islands travel package include?
Rental cars, hotels and flights, or any combination of the three — it's your pick! Whether you're exploring Caribbean Islands with the entire family or traveling by yourself, there's a bundle to suit your budget and style. Once you've made your booking, why not add on a couple of tours as well?
What should I know before booking a Caribbean Islands travel package?
So many places to venture to, so many things to see and do. With a package, you'll be able to tick more of them off your list. Combine your flights, rental cars and hotels and score big savings.
Can I choose my airline with a Caribbean Islands Expedia vacation package?
With a vacation package, you're always in charge. Whether you're looking to fly to Caribbean Islands in coach or business class, simply choose from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Caribbean Islands vacation package?
Whether it's your hotel or flight, yes, you can amend or cancel it. Locked in your Caribbean Islands vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a charge from your hotel, airline or car rental company. For more information, take a look at our Customer Service Portal. We're here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.