Caribbean Islands Vacation Packages 2026 from $596

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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.

Simpson Bay Resort, Marina & Spa

Pelican Key

$596

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (1,987 reviews)

Great stay. Beach was nearby, food was good. Nearby clubs.

Reviewed on Sep 4, 2026

The Villas at Simpson Bay Resort

Pelican Key

$638

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,525 reviews)

La Playa Orient Bay

$828

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.4/10 Exceptional! (785 reviews)

Fabulous stay! Beautiful resort right on Orient Bay!

Reviewed on Aug 26, 2026

Divi Little Bay Beach Resort

$663

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

8.2/10 Very Good! (1,012 reviews)

Divi little Bay resort did not fail my husband and I on our first time to St Maarten. The rooms were nice and clean and comfortable, the staff were all friendly and very knowledgeable. We felt like family after the first night. Our faces were remembered by the staff and that made us feel welcomed.

Reviewed on Sep 4, 2026

Hotel La Plantation

$648

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

8.8/10 Excellent! (656 reviews)

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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 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 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 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.

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.

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.

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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.

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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.

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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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Caribbean Islands Hotel Deals

Grand Hyatt Baha Mar

One Baha Mar Boulevard Nassau New Providence

Fully refundableReserve now, pay when you stay

$345 nightly

$378 total

Sep 27 - Sep 28

Total with taxes and fees

8.8/10 Excellent! (5,548 reviews)

"Just perfect"

Reviewed on Sep 5, 2026

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Playas de Bavaro Punta Cana La Altagracia

Fully refundableReserve now, pay when you stay

$299 nightly

$382 total

Oct 5 - Oct 6

Total with taxes and fees

Wyndham Alltra Punta Cana All-Inclusive Resort

Playas Uvero Alto Punta Cana La Altagracia

Fully refundableReserve now, pay when you stay

$226 nightly

$226 total

Sep 13 - Sep 14

Total with taxes and fees

8.8/10 Excellent! (1,455 reviews)

"Me encantó el trato de todo el personal,sus facilidades,la comida estaba riquísima.Sin duda regresamos y muy recomendado."

Reviewed on Sep 4, 2026

See all 89,042 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.