Caribbean Islands Vacations 2025 from CA $1,132

Caribbean Islands flight + hotel packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

per person

May 15 - May 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) 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.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Calgary (YYC) 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 Orient Bay Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Calgary (YYC) 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 Dawn Beach are located nearby.

Holland House Beach Hotel

Save 100% on your flight

per person

Apr. 24 - Apr. 30

found 1 day ago

Roundtrip flight included

Moncton (YQM) to Philipsburg (SXM)

Stay at this 4-star beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.

Oceans at Divi Little Bay

Save 100% on your flight

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Philipsburg (SXM)

Stay at this 4-star hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho 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 $427

CA $665 total

includes taxes & fees

9 Mar - 10 Mar

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 Cabbage Beach are located nearby.

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 $680

CA $803 total

includes taxes & fees

1 Apr - 2 Apr

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

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 $549

CA $648 total

includes taxes & fees

1 Apr - 2 Apr

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.

Barceló Bávaro Palace - All Inclusive

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

CA $642

CA $822 total

includes taxes & fees

23 Mar - 24 Mar

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 Los Corales Beach are located nearby.

On private beach

Pool

Hotel Riu Montego Bay - Adults Only - All Inclusive

Mahoe Bay, Ironshore, Montego Bay, Saint James

Get rates

Stay at this 4-star beach property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach and Sunset Beach Resort Au Natural Beach are located nearby.

Pool

Hot tub

Excellence Punta Cana - Adults Only All Inclusive

Playas Uvero Alto - Punta Cana, Punta Cana, La Altagracia

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Stay at this 5-star luxury property in Punta Cana. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions Macao Beach and Sirenis Aquagames Water Park 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

Eagle Beach

4.5/5(85 reviews)

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.

Port of San Juan

4.5/5(161 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.

Grace Bay Beach

5/5(107 reviews)

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 and enjoy its seafood restaurants.

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 $1,132. 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.