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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
Oct 19 - Oct 26
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,192 reviews)
Beautiful location, rooms are spacious and food was AMAZING!

Reviewed on Jul. 31, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,192 reviews)
Food option need to be upgraded. But the restaurant the food was delious.

Reviewed on Jul. 30, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
8.6/10 Excellent! (891 reviews)
Parking not much parking and very tight spaces

Reviewed on Jul. 29, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (938 reviews)
Loved it! Highly recommend!

Reviewed on Jul. 30, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
10’s across the board.

Reviewed on Aug. 1, 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?

 

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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 $331 per night from Sep 1 to Sep 2
CA $331
CA $543 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (4,299 reviews)
"Amazing property- great vibe, good and attentive staff and lots to do for kids and adults alike!"

Reviewed on Jul. 29, 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 $466 per night from Sep 1 to Sep 2
CA $466
CA $596 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (5,379 reviews)
"Expedia promised a bottle of wine during my stay which I never received. The resort staff was wonderful but air conditioning was lacking through restaurants at the resort. We felt ver sorry for the staff having to work in those conditions"

Reviewed on Jul. 31, 2025

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
6063 Isla Verde Avenue, Carolina
Fully refundableReserve now, pay when you stay
The price is CA $483 per night from Aug 31 to Sep 1
CA $483
CA $648 total
Aug 31 - Sep 1
includes taxes & fees
8.4/10 Very Good! (1,868 reviews)
"Very polite customer service, the beach is very warm and nice!"

Reviewed on Jul. 29, 2025

Fairmont El San Juan Hotel
See all 81,014 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

4.5/5(85 reviews)

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

5/5(107 reviews)

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

4.5/5(213 reviews)

Nothing says vacation like spending a lazy day at Bavaro Beach, a popular beach in Punta Cana. Discover the top-notch restaurants and great live music in this romantic area.

Bavaro Beach

Frequently asked questions

How much does a Caribbean Islands vacation package cost?
Perhaps much less than you think — from only CA $925, 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.