Caribbean Islands Vacations 2026 from CA $2,050

Caribbean Islands flight + hotel packages

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

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $2,050

per person

Feb 2 - Feb 9

found 22 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Philipsburg (SXM)

Book a stay at this 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.

The Villas at Simpson Bay Resort

CA $2,333

per person

Feb 2 - Feb 9

found 22 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Philipsburg (SXM)

Book a stay at this 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.

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $2,093

per person

Jan 17 - Jan 24

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

Book a stay at this 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.

Holland House Beach Hotel

Downtown Philipsburg

CA $2,911

per person

Feb 20 - Feb 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

Book a stay at this 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

CA $2,728

per person

Feb 2 - Feb 9

found 22 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Philipsburg (SXM)

Stay at this hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.

Top Caribbean Islands hotels deals

Grand Hyatt Baha Mar

One Baha Mar Boulevard Nassau New Providence

CA $467

CA $710 total

Jan 3 - Jan 4, 2026

includes taxes & fees

Book a stay at this luxury resort in Nassau. Enjoy free WiFi, free parking, and 8 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cable Beach and The Current Baha Mar Gallery and Art Center are located nearby.

Hotel Riu Republica - Adults only - All Inclusive

Playa Arena Gorda Punta Cana

Get rates

Book a stay at this beach property in Punta Cana. Enjoy free breakfast, free WiFi, and 9 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cana Bay Golf Club and Arena Gorda Beach are located nearby.

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Playas de Bavaro Punta Cana La Altagracia

CA $557

CA $713 total

Jan 11 - Jan 12, 2026

includes taxes & fees

Book a stay at this 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

Majestic Elegance Punta Cana - All Inclusive

Playa Bavaro - Punta Cana Punta Cana La Altagracia

CA $583

CA $583 total

Dec 17 - Dec 18

includes taxes & fees

Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Arena Gorda Beach and Cana Bay Golf Club are located nearby.

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

6307 Casino Drive Paradise Island New Providence

Get rates

Book a stay at this beach property in Paradise Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cable Beach and Marina Village at Atlantis are located nearby.

Hyatt Vacation Club at Hacienda del Mar, Dorado

301 Hwy 693 Vega Alta

Free cancellation

CA $302

CA $389 total

Dec 17 - Dec 18

includes taxes & fees

Book a stay at this beach resort in Vega Alta. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Dorado Beach and Playa de los Tocones are located nearby.

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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 $2,050. 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.