Caribbean Islands Vacations 2026/2026 from CA $1,399

Caribbean Islands flight + hotel packages

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

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

CA $1,399

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. 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

CA $2,990

per person

Jan 29 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) 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 $3,238

per person

Feb 1 - Feb 7

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) 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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $2,371

per person

Feb 1 - Feb 7

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) 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 Morgan Resort Spa Village

CA $2,338

per person

Feb 1 - Feb 7

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Philipsburg (SXM)

Book a stay at this spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant 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 $419

CA $653 total

Dec 14 - Dec 15

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.

Pool

Spa

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Playas de Bavaro Punta Cana La Altagracia

Free cancellation

Reserve now, pay when you stay

CA $602

CA $771 total

Jan 6 - Jan 7, 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

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.

Pool

Hot tub

Majestic Elegance Punta Cana - All Inclusive

Playa Bavaro - Punta Cana Punta Cana La Altagracia

CA $585

CA $585 total

Dec 9 - Dec 10

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.

On private beach

Pool

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.

Pool

Breakfast included

Hyatt Vacation Club at Hacienda del Mar, Dorado

301 Hwy 693 Vega Alta

Free cancellation

CA $240

CA $322 total

Dec 15 - Dec 16

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.

Pool

Hot tub

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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

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.

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.

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, 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 $1,399. 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.