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

Oyster Pond
CA $1,230
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,010 reviews)
Overall a great experience. Runs were very clean and plenty of AC. The pill was nice, just needs a little maintenance on tiles to be really nice. The staff was awesome-CeeJay, Chris and Nubi at the Veranda were very nice and fun to be around. The only downside was the whiff of sewer that was coming from somewhere in the area near the entrance of the property, but never smelled it from rims or anywhere else. We had a great time.

Reviewed on Sep 6, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,299
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
I loved it. Beautiful property, easily accessible entertainment and food (my biggest priorities lol). I will definitely be back.

Reviewed on Sep 7, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,710
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Dinner on the beach was excellent view and music

Reviewed on Sep 6, 2026

La Playa Orient Bay

La Playa Orient Bay

CA $1,353
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (785 reviews)
Fabulous stay! Beautiful resort right on Orient Bay!

Reviewed on Aug 26, 2026

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
CA $1,654
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The View🏖️

Reviewed on Sep 1, 2026

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
A beach with clear turquoise water, palm trees, and a hotel in the background.

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
A beach with clear turquoise water, white sand, and a few footprints. There are houses and palm trees in the background.

Grace Bay

This picturesque stretch of white sand and warm, turquoise water is home to luxury resorts, restaurants and one of the world’s largest barrier reefs.

Find hotels in Grace Bay
A densely packed urban area with colorful buildings and a clear sky.

Old San Juan

The fascinating museums and captivating waterfront views are top of the list for many visitors to Old San Juan. A stop by Port of San Juan or Castillo de San Cristobal might round out your trip.

Find hotels in Old San Juan
A beach with a boat, palm trees, and a city skyline in the background.

Isla Verde

White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.

Find hotels in Isla Verde
A sandy beach with palm trees, a rocky breakwater, and calm ocean waves.

Condado

Oceanfront and upscale, Condado boasts picturesque beaches alongside hotels, nightclubs, casinos, and shops. Stroll through La Ventana al Mar park, and enjoy easy access to public transport via T21 and D53 bus routes.

Find hotels in Condado

Things to do in Caribbean Islands

The Caribbean Islands are perfect for beach and culture-themed vacations, offering a variety of outdoor activities. Tourists can enjoy beach vacations, golf experiences, and beachfront relaxation, along with thrilling underwater sports like snorkeling. For those seeking adventure, the islands provide exciting island excursions. With a stunning natural backdrop, the Caribbean promises unforgettable experiences for every traveller.

*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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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

One Baha Mar Boulevard Nassau New Providence
Fully refundableReserve now, pay when you stay
CA $311
CA $523 total
Sep 27 - Sep 28
includes taxes & fees
Grand Hyatt Baha Mar
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Playas de Bavaro Punta Cana La Altagracia
Fully refundableReserve now, pay when you stay
CA $413
CA $529 total
Oct 7 - Oct 8
includes taxes & fees
8.4/10 Very good! (7,436 reviews)
"."

Reviewed on Sep 7, 2026

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Wyndham Alltra Punta Cana All-Inclusive Resort

Wyndham Alltra Punta Cana All-Inclusive Resort

Playas Uvero Alto Punta Cana La Altagracia
Fully refundableReserve now, pay when you stay
CA $313
CA $313 total
Sep 13 - Sep 14
includes taxes & fees
Wyndham Alltra Punta Cana All-Inclusive Resort
See all 88,903 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.
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Stay near popular Caribbean Islands attractions

A beach scene with a flag, beach chairs, umbrellas, and a vendor cart.

Eagle Beach

9.4/10 (6,014 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.
See properties
A cruise ship docked near a coastal city with buildings and palm trees.

Port of San Juan

9.0/10 (16,423 reviews)
Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene.
See properties
A beach with people walking, clear blue water, and green vegetation in the foreground.

Grace Bay Beach

9.8/10 (5,552 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.
See properties
A beach with palm trees and turquoise water.

Bavaro Beach

8.8/10 (36,026 reviews)
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.
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A beach with a lifeguard tower, palm trees, and a clear blue sky.

Luquillo Beach

9.0/10 (3,887 reviews)
Sample local street food or doze under a palm tree on this picturesque stretch of coast.
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A coastal resort area with a beach, clear turquoise waters, and a clear sky.

Punta Cana Beach

8.8/10 (30,329 reviews)
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.
See properties
A tropical beach with clear turquoise waters, thatched umbrellas, and palm trees.

Mambo Beach

8.8/10 (2,288 reviews)
Nothing says vacation like spending a lazy day at Mambo Beach, a popular beach in Willemstad. Stroll along the seaside or visit the shops in this romantic area.
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A waterfall cascading over rocks in a lush, green forest.

El Yunque National Forest

9.2/10 (3,268 reviews)
This tropical rainforest offers many great hiking options, including stunning mountain views and beautiful waterfalls.
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Frequently asked questions

How much does a Caribbean Islands vacation package cost?
Perhaps much less than you think — from only CA $1,230, 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.