Caribbean Islands Vacation Packages 2026 from $722

The Latest Caribbean Islands vacation packages

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

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$722

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,442 reviews)

First off great location can walk to alot of local favorites. OMG where do we start Anna I hope is her name was super professional and helpful explained everything the process was amazing! Fernando wow he remembered our names each time he saw us checked on us just overall a great person to connect while traveling. Our favorite person would probably be Sophia. She was so amazing. She worked outside at the pool bar how she laughed talked and joked answer questions gave suggestions just her positivity her remembering your name your favorite drink oh my God I will come back just for her Sophia, thank you for making our visit one of the best visits at a hotel resort totally worth it the gold bathing suit Group loved you

Reviewed on Jul 15, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$744

per person

Sep 2 - Sep 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (1,837 reviews)

Nice stay but I’d say it’s A long walk depending where in the resort you stay to all the other places

Reviewed on Jul 14, 2026

Coral Beach Club Villas & Marina

Oyster Pond

$1,071

per person

Sep 21 - Sep 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (117 reviews)

Great location and property

Reviewed on Jul 11, 2026

The Morgan Resort Spa Village

$981

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (2,255 reviews)

Rooms were so pretty; my only complaint was that I wish the pool area stayed open longer. It was very pretty outside, and I would have loved to sit by the ocean at night

Reviewed on Jul 15, 2026

Hotel La Plantation

$783

per person

Aug 28 - Sep 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

8.8/10 Excellent! (629 reviews)

Great resort for a family ! Breakfast was good but I wouldn’t consider it to be a buffet as I feel like they could have a little more options for breakfast. Daily room service and room clean to the T.

Reviewed on Jul 9, 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

Stay near popular Caribbean Islands attractions

Caribbean Islands Hotel Deals

Grand Hyatt Baha Mar

One Baha Mar Boulevard Nassau New Providence

Fully refundableReserve now, pay when you stay

$426 nightly

$466 total

Aug 2 - Aug 3

Total with taxes and fees

8.6/10 Excellent! (5,307 reviews)

"The staff were very nice, the grounds were well maintained, and the amenities were useful."

Reviewed on Jul 14, 2026

Hyatt Regency Grand Reserve Puerto Rico

200 Coco Beach Blvd. Highway 955-I Río Grande

Fully refundableReserve now, pay when you stay

$329 nightly

$359 total

Aug 10 - Aug 11

Total with taxes and fees

9/10 Wonderful! (3,073 reviews)

"It was a good stay but make sure you bring your card with you."

Reviewed on Jul 14, 2026

Ocean Blue & Sand Beach Resort - All Inclusive

Car. Arena Gorda Punta Cana La Altagracia

$329 nightly

$329 total

Jul 30 - Jul 31

Total with taxes and fees

8.6/10 Excellent! (5,619 reviews)

"Overall excellent place, very friendly and professional staff, we loved our stay. The only thing we weren’t happy about was that the pool closed at 7… it would have been nice to have some evening swims. Also great transportation accommodations available onsite!"

Reviewed on Jul 15, 2026

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.

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.