Caribbean Islands Vacations 2025/2026 from CA $1,038

Caribbean Islands flight + hotel packages

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

Esmeralda Resort

per person

Aug 26 - Aug 30

found 24 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

Stay at this 4-star beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Coral Beach Club Villas & Marina

Oyster Pond

per person

Sep 26 - Oct 3

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

Stay at this 4-star beach resort in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

The Villas at Simpson Bay Resort

per person

Sep 1 - Sep 6

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Philipsburg (SXM)

Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

per person

Sep 1 - Sep 6

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Philipsburg (SXM)

Stay at this 3.5-star family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Hilton Vacation Club Royal Palm St. Maarten

per person

Oct 6 - Oct 12

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Philipsburg (SXM)

Stay at this 4-star beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Top Caribbean Islands hotels deals

Grand Hyatt Baha Mar

One Baha Mar Boulevard, Nassau, New Providence

Free cancellation

Reserve now, pay when you stay

CA $328

CA $538 total

Aug 25 - Aug 26

includes taxes & fees

Stay at this 4.5-star luxury resort in Nassau. Enjoy free WiFi, free parking, and 8 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular attractions Cable Beach and The Current Baha Mar Gallery and Art Center are located nearby.

Pool

Spa

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Playas de Bavaro, Higuey, Punta Cana, La Altagracia

Free cancellation

Reserve now, pay when you stay

CA $549

CA $648 total

Aug 19 - Aug 20

includes taxes & fees

Stay at this 5-star luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bavaro Beach and Los Corales Beach are located nearby.

Pool

Breakfast included

Fairmont El San Juan Hotel

6063 Isla Verde Avenue, Carolina

Free cancellation

Reserve now, pay when you stay

CA $476

CA $640 total

Jul 27 - Jul 28

includes taxes & fees

Book a stay at this beach resort in Carolina. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Condado Beach and Pan American Pier are located nearby.

Pool

Spa

Barceló Bávaro Beach - Adults Only - All Inclusive

Carretera Bávaro Km. 1, Playa Bávaro, Punta Cana, La Altagracia

CA $315

CA $404 total

Aug 19 - Aug 20

includes taxes & fees

Stay at this 4-star beach property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bavaro Beach and Los Corales Beach are located nearby.

Pool

Breakfast included

Hyatt Regency Grand Reserve Puerto Rico

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

Free cancellation

Reserve now, pay when you stay

CA $283

CA $364 total

Jul 27 - Jul 28

includes taxes & fees

Stay at this 4-star beach resort in Río Grande. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Luquillo Beach and Wyndham Rio Mar Golf Course are located nearby.

Pool

Hot tub

Serenade Punta Cana Beach & Spa Resort - All Inclusive

Carretera Cabeza de Toro, Punta Cana, La Altagracia

Free cancellation

Reserve now, pay when you stay

CA $322

CA $380 total

Aug 26 - Aug 27

includes taxes & fees

Stay at this 4.5-star luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bavaro Beach and Cabeza de Toro Beach are located nearby.

On private beach

Pool

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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.

Popular places to visit

Port of San Juan

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

Nothing says vacation like spending a lazy day at Eagle Beach, a popular beach in Oranjestad-West. Make time to visit the shops and casinos while you're in the area.

Grace Bay Beach

Nothing says vacation like spending a lazy day at Grace Bay Beach, a popular beach in Grace Bay. Amble around this romantic area's seaside, or seek out the snorkeling spots.

Frequently asked questions

How much are vacation packages to Caribbean Islands?

Travelocity has package deals to Caribbean Islands, as well as flights and hotels, from an impressive CA $1,038. With all that extra cash, you could throw in some cool tours or maybe tack on a couple of extra days to your exciting getaway.

Where can I get the best vacation package deals for Caribbean Islands?

There are amazing Caribbean Islands package deals to score with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the world? Keep this in mind the next time you're ready to tick another destination off your travel bucket list.

Why should I purchase my Caribbean Islands vacation package with Travelocity?

Fantastic savings, countless exciting destinations and 24/7 customer service you can rely on — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always score the best possible deal with Travelocity.

Can I save on my Caribbean Islands car rental if I combine it with a hotel or flight?

Sure can. And our Caribbean Islands vacation packages are the perfect way to do it. With just a few clicks you can save cash and time by combining your bookings. Pick up the keys to your rental car and feel the freedom of the open road. Need to fill your itinerary? Throw some tours or experiences into your package and make savings on those too.

Which airport is best for Caribbean Islands?

The major airport in Caribbean Islands is Las Americas Intl. Airport (SDQ).

What is there to do in Caribbean Islands?

Caribbean Islands boasts hidden gems at every turn, but make sure you plan a trip to Dunn's River Falls and Dickenson Bay Beach while you're here. These attractions are a must-see.