Caribbean Islands Vacation Packages 2026 from $790

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

$790

per person

Oct 3 - Oct 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,001 reviews)

This is my 2nd time staying at the property. The property & room are clean, I did not use the pool, but I could see it from my ocean view room. It does not appear that any other guest used it either. The breakfast was nothing much... my 1st stay we were given ham & cheese croissants, this time just plain ( I assume a budgeting issue). The Ham and cheese croissants is much preferred. Also came with coffee, creamer, chocolate croissant & orange juice (not fresh). The kitchenette was in great condition and super clean.

Reviewed on Jul 8, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$902

per person

Oct 3 - Oct 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,442 reviews)

The bar at the pool should stay open later.

Reviewed on Jul 14, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$824

per person

Oct 3 - Oct 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (1,837 reviews)

Excellent location, clean and very comfortable.!

Reviewed on Jul 14, 2026

Divi Little Bay Beach Resort

Save 100% on your flight

$1,748

per person

Aug 15 - Aug 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

8.2/10 Very Good! (1,010 reviews)

The overall experience was great! The Bellmen were awesome, helpful, and knowledgeable about rides to your room and taxi fees. The check-in staff was accommodating and respectful. The property was exceptionally clean for the number of people wandering around. The room, an efficiency, was clean and spacious with a Jacuzzi tub, a full refrigerator, and a few ants and flying insects to be expected. Overall, my wife and I had a ball! Get to Gizmos early for the Jerk skewers, for they sell out fast!

Reviewed on Jul 14, 2026

Oceans at Divi Little Bay

Save 100% on your flight

$1,946

per person

Aug 15 - Aug 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

8.2/10 Very Good! (451 reviews)

Poor customer service, I booked with a discover card and wasn’t allowed to use a discover card there. Got charged twice for my suitcase. Only the roof top bar was good, I’m anssum cause it was an extra $45 per person and the pizza from slice was great. Overall I wouldn’t do it again and you should rent a car because taxis charge too much. Get your own wifi plan before you go. The water I showered with smelled bad and gave me rashes all over my skin. Laundry room doesn’t work properly. Also when I visited pure oceans restaurant for dinner I sent back pasta because it was hard, I caught the cook putting the same food back on another plate to give it back to me and the list goes on…..

Reviewed on Jul 14, 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

$424 nightly

$465 total

Jul 28 - Jul 29

Total with taxes and fees

8.6/10 Excellent! (5,296 reviews)

"You need to make reservations way in advance for dining after 5pm. Food is very expensive but overall we enjoyed and will visit again"

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

$306 nightly

$333 total

Jul 19 - Jul 20

Total with taxes and fees

9/10 Wonderful! (3,063 reviews)

"Comodidad y el trato del personal"

Reviewed on Jul 13, 2026

Ocean Blue & Sand Beach Resort - All Inclusive

Car. Arena Gorda Punta Cana La Altagracia

$339 nightly

$339 total

Jul 21 - Jul 22

Total with taxes and fees

8.6/10 Excellent! (5,652 reviews)

"Nice staff .nice sand in the beach"

Reviewed on Jul 14, 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.