Caribbean Islands Vacation Packages 2026 from $689

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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 traveling, Expedia will help turn your Caribbean Islands vacation into a reality.

The Latest Caribbean Islands vacation packages

Price found within the past 48 hours. Click for updated prices.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$689

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,001 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,103

per person

Nov 13 - Nov 20

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$793

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

This was a very beautiful room. We stayed in the I bedroom ocean view suite. It was clean and well maintained. The decor was lovely. The beds were perfect. Kitchen was clean and well equipped. My favorite part was the balcony which overlooked Simpson bay. Would 100% stay there again.

Reviewed on Oct 13, 2026

The Morgan Resort Spa Village

Save 100% on your flight

$885

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,412 reviews)

Loved everything about this hotel & the staff. Would recommend 10x over!

Reviewed on Oct 13, 2026

Oceans at Divi Little Bay

Save 100% on your flight

$2,682

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

8.4/10 Very Good! (586 reviews)

I love everything about the resort, I would highly recommend

Reviewed on Oct 13, 2026

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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.

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.

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.

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.

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.

Stay near popular Caribbean Islands attractions

A coastal city with a long sandy beach, clear turquoise waters, and a mix of urban and resort buildings.

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.

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A coastal town with a beach, clear blue waters, and a large hotel complex.

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.

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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 relaxing area's seaside and enjoy its lively bars.

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A coastal resort with a beach, palm trees, and a clear blue sea.

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 top-notch restaurants and great live music in this romantic area.

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A beach with a lifeguard tower, palm trees, and ocean waves.

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 waterfall cascading over rocky terrain surrounded by lush greenery.

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.

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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Caribbean Islands Hotel Deals

Wyndham Alltra Punta Cana All-Inclusive Resort

Playas Uvero Alto Punta Cana La Altagracia

$253 nightly

$253 total

Oct 20 - Oct 21

Total with taxes and fees

8.8/10 Excellent! (1,556 reviews)

"Everything was great the customer service was amazing especially Rogelio he was the best"

Reviewed on Oct 13, 2026

Grand Hyatt Baha Mar

One Baha Mar Boulevard Nassau New Providence

Fully refundableReserve now, pay when you stay

$358 nightly

$392 total

Oct 31 - Nov 1

Total with taxes and fees

8.8/10 Excellent! (5,642 reviews)

"Amazing! Even booked the kids club for me son and he had a great experience 2nd time here we’ll definitely be back !"

Reviewed on Oct 13, 2026

Hotel Riu Montego Bay - Adults Only - All Inclusive

Mahoe Bay, Ironshore Montego Bay Saint James

8.6/10 Excellent! (5,638 reviews)

"What I liked about my stay was housekeeping cleaned your rooms well and the hotel app helped with assistance with requesting maintenance, housekeeping, mini bar requests. I had to keep following up with the front desk in person or by phone to ensure requests were completed. For example, the room ..."

Reviewed on Oct 13, 2026

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See all 89,035 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.

Find the Best Caribbean Islands Vacation Packages

Things to do in Caribbean Islands

The Caribbean Islands offer a perfect blend of beach relaxation and cultural exploration. Visitors can enjoy a variety of activities, including underwater sports like scuba diving with provided gear, and adventure activities that include exploring pirate coves. Golf enthusiasts will find excellent courses, while the surrounding recreational areas provide ample opportunities for outdoor fun. A trip to the Caribbean promises unforgettable experiences for every type of traveler.

*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.

Calendar Month	Temperature	Precipitation	Cloudiness
January	79.3°F (26.3°C)	No Rain	Mostly Sunny
February	78.8°F (26.0°C)	No Rain	Mostly Sunny
March	79.2°F (26.200000000000003°C)	No Rain	Mostly Sunny
April	80.1°F (26.700000000000003°C)	Light Rain	Mostly Sunny
May	80.4°F (26.9°C)	Light Rain	Mostly Sunny
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny
July	82.2°F (27.9°C)	Light Rain	Mostly Sunny
August	82.8°F (28.200000000000003°C)	Light Rain	Mostly Sunny
September	82.9°F (28.3°C)	Light Rain	Mostly Sunny
October	82.6°F (28.1°C)	Light Rain	Mostly Sunny
November	78.3°F (25.700000000000003°C)	Light Rain	Mostly Sunny
December	79.5°F (26.4°C)	No Rain	Mostly 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.

More vacations you might like

Frequently asked questions

How do vacation package prices compare across popular destinations in the Caribbean Islands?

For a week-long Caribbean Islands vacation package, prices vary significantly across popular destinations, with San Juan offering some of the lowest typical prices and Noord having the highest. For example, a week-long trip to San Juan typically costs around $1,150 per adult, with prices ranging from around $600 to $2,000. Punta Cana and Montego Bay are often around $1,550 per adult, with Punta Cana packages ranging from around $850 to $2,700 and Montego Bay packages from around $1,000 to $2,400. Paradise Island typically sees prices around $1,900 per adult, ranging from around $1,100 to $3,350. Noord is generally the highest, with week-long packages around $2,350 per adult, and prices ranging from around $1,450 to $3,900.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How can I save money on a Caribbean Islands vacation package?

When you bundle, you can save up to 30%*. To save money on a Caribbean Islands package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's included in a Caribbean Islands vacation package?

A Caribbean Islands vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations like Punta Cana, San Juan, or Paradise Island. In Punta Cana, most hotels offer airport shuttle service and free breakfast. For San Juan, nearly all hotels provide airport shuttle service to and from Luis Muñoz Marín International Airport (SJU), and about half include free breakfast. On Paradise Island, nearly all hotels offer airport shuttle service to and from Lynden Pindling International Airport (NAS) and free breakfast.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

Which destinations in the Caribbean Islands offer the best-value vacation package deals?

San Juan, Sosúa, Punta Cana, Montego Bay, and Paradise Island are some of the top destinations for cheap Caribbean Islands vacation package deals. For an affordable weekend getaway, San Juan is often among the most budget-friendly options, with package prices starting around $500 per adult. For notable bundle savings, Paradise Island is often among the best options, with flight-and-hotel bundles saving around $265 per adult.Browse cheap vacation packages in the Caribbean Islands on Expedia to compare current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

When is the best time to visit the top destinations in the Caribbean Islands?

The best time for a Caribbean Islands vacation package depends on which destination you choose.Punta Cana is busiest in July and December, when average temperatures are around 82°F and 78°F respectively. If you'd prefer fewer crowds, January is quieter, with average temperatures around 77°F.San Juan sees its highest demand in December, March, and July, with average temperatures around 77°F in December and 82°F in July. You can also catch events like Fiestas de la Calle in January or Monster Jam San Juan in October. For a quieter trip, October is typically less busy, with average temperatures around 81°F.Noord is most popular in July and August, with average temperatures around 82°F. If you prefer fewer visitors, February is a quieter month, with average temperatures around 79°F.Montego Bay experiences peak demand in December and June, with average temperatures around 78°F and 82°F respectively. For a more relaxed visit, January is quieter, with average temperatures around 77°F.

What package types are available across the top destinations in the Caribbean Islands?

The Caribbean Islands offer a variety of vacation package types across popular destinations like Punta Cana, San Juan, Paradise Island, Noord, and Montego Bay:

All-inclusive: In Punta Cana, the 5-star Majestic Mirage Punta Cana, All Suite Resort, rated 8.7 out of 10 by travelers, features a kids club and rooms that travelers describe as neat and clean.
Best Value: For budget-friendly options, The Looking Glass Hotel in San Juan is rated 8.7 out of 10 by travelers and provides free WiFi, with travelers absolutely loving the rooms.
Couples: In Punta Cana, Hotel Castillo Real, rated 8.3 out of 10 by travelers, offers air conditioning for a comfortable stay.
Family: The 5-star Paradisus Palma Real Golf & Spa Resort All Inclusive in Punta Cana, rated 8.3 out of 10 by travelers, provides a kids club, and travelers frequently praise the amazing rooms.
Luxury: In Punta Cana, the 5-star Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive, rated 9.3 out of 10 by travelers, boasts a waterpark, and travelers highlight the fantastic pool.

Which destinations should I consider for a Caribbean Islands vacation?

For a Caribbean Islands vacation, you can choose a destination that best matches your travel style:

Punta Cana: A popular package base, this city is ideal for all-inclusive and couples' trips, offering a wide array of resorts and activities.
Sosúa: Consider this destination for family-friendly packages or a romantic getaway, with options that cater to various budgets.
St. Barthelemy: For a luxury or romantic escape, St. Barthelemy provides upscale experiences, particularly appealing to couples.
Noord: This area is a strong choice for beach-focused vacations and couples, with many lodging options that emphasize coastal access.
Montego Bay: A well-established package destination, Montego Bay is excellent for all-inclusive family vacations and those interested in cultural attractions.

Is Caribbean Islands better suited for a beach vacation or a cultural trip?

The Caribbean Islands are primarily known for their stunning beaches, making them an excellent choice for a beach vacation. Destinations like Punta Cana offer expansive shores such as Punta Cana Beach, perfect for sun and sand relaxation.However, the region also boasts a rich cultural side. Cities like San Juan provide a blend of historic charm and urban attractions, including landmarks like the Jose Miguel Agrelot Coliseum. Montego Bay also offers cultural experiences, such as the historic Rose Hall Great House.Ultimately, a Caribbean Islands vacation package can cater to both beach lovers and those seeking cultural exploration, depending on the specific island or city you choose.

What are the top things to do across the destinations in the Caribbean Islands?

A Caribbean Islands vacation offers a diverse range of activities across its many destinations, from vibrant beaches to historic sites.Browse and book things to do in the Caribbean Islands on Expedia.

Which destinations in the Caribbean Islands have all-inclusive resorts?

You'll find all-inclusive resorts in the Caribbean Islands across several popular destinations, perfect for a Caribbean Islands vacation package:Browse all-inclusive resorts in the Caribbean Islands on Expedia.

Are there family vacation packages in the Caribbean Islands with kid-friendly amenities?

Yes, family vacation packages in the Caribbean Islands often feature resorts with excellent kid-friendly amenities across various destinations:

Nickelodeon Hotels & Resorts Punta Cana, Gourmet All Inclusive by Karisma: In Punta Cana, this 5-star property offers a kids club, indoor pool, and babysitting services, with travelers praising the great food and hard-working staff.
DoubleTree by Hilton San Juan: In San Juan, this 4-star hotel, rated 8.6 out of 10 by travelers, provides family rooms and a game room, and travelers highlight its perfect location and convenient food options.
Harborside Resort & Vacation Rentals at Atlantis: On Paradise Island, this 4-star resort, rated 7.5 out of 10 by travelers, includes kitchenettes and a playground, and travelers appreciate its clean facilities and great food.
Embassy Suites By Hilton Aruba Beach Resort: In Noord, this 4-star resort, rated 8.7 out of 10 by travelers, features a kids club and kitchenettes, with travelers noting the amazing rooms and quiet location.
Half Moon: In Montego Bay, this 5-star resort, rated 9.1 out of 10 by travelers, offers a kids club and kitchenettes, and travelers often mention its clean location and overall spaciousness.

What luxury vacation packages are available in the Caribbean Islands?

Luxury Caribbean Islands vacation packages can be found across several upscale destinations, offering premium stays:Browse luxury vacation packages in the Caribbean Islands on Expedia to compare options.

Which destinations in the Caribbean Islands have adults-only resorts?

Several destinations in the Caribbean Islands offer adults-only resorts that can be part of your Caribbean Islands vacation package:Browse adults-only resorts in the Caribbean Islands on Expedia to compare.

When should I book vacation packages for the top destinations in the Caribbean Islands?

Most Caribbean Islands vacation packages are booked around 5 to 8 weeks ahead, though the ideal timing can vary by destination.Travelers tend to book Caribbean Islands vacation packages most often in March, from June to August, and from October to November. If you're planning a spontaneous getaway, Expedia also offers last-minute Caribbean Islands vacation packages.

How many days do you need for a Caribbean Islands vacation?

Most Caribbean Islands vacation packages last around 4 to 5 days, but the ideal trip length depends on where you're going and what you'd like to experience.Punta Cana, known for its beautiful beaches and outdoor activities, is often enjoyed over around 5 days. While week-long trips are most popular, some travelers also opt for weekend or two-week stays, allowing time to relax on Punta Cana Beach.For San Juan, a vibrant city with beaches and cultural attractions, a trip of around 4 days is typical. Many travelers choose week-long stays, though weekend trips are also common, providing enough time to explore areas like Condado Beach.Paradise Island, a destination known for its city attractions and romantic beaches, is also typically visited for around 4 days. Week-long trips are popular here, with some choosing shorter weekend getaways to enjoy spots like Cabbage Beach.

Can I change or cancel my Caribbean Islands vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Caribbean Islands vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Caribbean Islands vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Caribbean Islands vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Caribbean Islands?

To find last-minute vacation packages to Caribbean Islands, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Caribbean Islands vacation packages?

Free cancellation on a Caribbean Islands vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Caribbean Islands vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Caribbean Islands getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Caribbean Islands vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Caribbean Islands Vacations from $689

Book a Hotel + Flight or Car together to unlock savings

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Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Caribbean Islands Vacation

The Latest Caribbean Islands vacation packages

Princess Heights Luxury Boutique Condo Hotel

Simpson Bay Resort, Marina & Spa

The Villas at Simpson Bay Resort

The Morgan Resort Spa Village

Oceans at Divi Little Bay

Where to stay in Caribbean Islands

Palm Beach

Old San Juan

Condado

Grace Bay

Isla Verde

Stay near popular Caribbean Islands attractions

Eagle Beach

Port of San Juan

Grace Bay Beach

Punta Cana Beach

Bavaro Beach

Luquillo Beach

El Yunque National Forest

Mambo Beach

Caribbean Islands Hotel Deals

Wyndham Alltra Punta Cana All-Inclusive Resort

Grand Hyatt Baha Mar

Hotel Riu Montego Bay - Adults Only - All Inclusive

Find the Best Caribbean Islands Vacation Packages

Things to do in Caribbean Islands

Best time to go to Caribbean Islands

Tips to save on your trip to Caribbean Islands

More vacations you might like

Frequently asked questions

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