Vacation Packages 2025/2026

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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.

Oyster Bay Beach Resort

Oyster Pond

Save 100% on your flight

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

8.6/10 Excellent! (885 reviews)

Excellent staff very friendly. They took care of all my needs. I would recommend this place. Most of the patrons that go there have been going there for years. I will definitely see about going back.

Reviewed on Jul 6, 2025

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

8.8/10 Excellent! (1,162 reviews)

Beautiful beach wonderful accommodations something for couples and families to do - courteous staff, helpful and friendly- pools are perfect - beach vibes and more of an adult pool by the hotel and villa's. Property is large with a few different types of accommodations.

Reviewed on Jul 8, 2025

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (935 reviews)

Driving the hills were unique to get to and from the hotel. I loved the comfort of the room and the views are beautiful. It's a gated community so I felt safe.

Reviewed on Jul 4, 2025

Hilton Vacation Club Royal Palm St. Maarten

Save 100% on your flight

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,041 reviews)

Over all I love this property. I stayed in a beach from apartment. it was lovely. I'm looking forward to going back to celebrate my birthday in August. The restaurant on the beach was amazing. Can't wait to go back.

Reviewed on Jul 8, 2025

Holland House Beach Hotel

Downtown Philipsburg

Save 100% on your flight

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,001 reviews)

The common area is beautiful. Combination of mahogany floors, black painted ceilings and white walls is absolutely soothing. I would give the staff more than 5-stars! The food is delicious. I loved everything about this property except there is no pool. But, the beach a literally a few steps away.

Reviewed on Jul 7, 2025

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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

Isla Verde

4/5(687 area reviews)

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

Discover the most popular places to visit in Caribbean Islands

San Juan Antiguo showing general coastal views and a coastal town

Port of San Juan

4.5/5(2,281 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.

Eagle Beach

4.5/5(1,687 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.

Bavaro Beach

4.5/5(3,857 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.

Caribbean Islands Hotel Deals

Grand Hyatt Baha Mar

One Baha Mar Boulevard, Nassau, New Providence

Fully refundableReserve now, pay when you stay

$401 nightly

$441 total

Jul 23 - Jul 24

Total includes taxes and fees

8.4/10 Very Good! (4,189 reviews)

"The property is beautiful and well kept. The casino was fun and the restaurants were delish. This would be a great place for a family to visit with the wildlife exhibits and little water park. We would be back with our kids but in the end, the resort staff hospitality has encouraged us to continue ..."

Reviewed on Jul 6, 2025

Fairmont El San Juan Hotel

6063 Isla Verde Avenue, Carolina

Fully refundableReserve now, pay when you stay

$422 nightly

$469 total

Jul 14 - Jul 15

Total includes taxes and fees

8.4/10 Very Good! (1,797 reviews)

"The property is located in a central area near the highway, Walgreens and beach. The housekeeping was attentive and serviced each day. Ubers were easily accessible Express entry to Club Brava Direct beach access Impecable property grounds Breakfast was plentiful and reasonably priced Daily Nightly ..."

Reviewed on Jul 8, 2025

Hyatt Regency Grand Reserve Puerto Rico

200 Coco Beach Blvd. Highway 955-I, Río Grande

Fully refundableReserve now, pay when you stay

$245 nightly

$267 total

Aug 4 - Aug 5

Total includes taxes and fees

8.8/10 Excellent! (2,316 reviews)

"Absolutely incredible. Perfect for kids, families or even couples!"

Reviewed on Jul 8, 2025

See all 80,925 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.