Caribbean Islands Vacations 2026 from CA $1,927

Caribbean Islands flight + hotel packages

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

La Vista Hotel

Pelican Key

CA $1,927

per person

Feb 28 - Mar 7

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Philipsburg (SXM)

Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

The Villas at Simpson Bay Resort

Pelican Key

CA $2,085

per person

Mar 27 - Apr 1

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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.

Coral Beach Club Villas & Marina

Oyster Pond

CA $3,983

per person

Apr 4 - Apr 11

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Book a stay at this 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.

Villa Amalia

CA $15,213

per person

Feb 21 - Feb 28

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Book a stay at this luxury vacation home in Philipsburg. Enjoy free WiFi, free parking, and private pools. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Royal Islander Resort La Plage

CA $2,321

per person

Mar 8 - Mar 15

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Philipsburg (SXM)

Book a stay at this beach resort in Lowlands. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the helpful staff 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 $505

per night

Feb 4 - Feb 5

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

CA $603

per night

Feb 4 - Feb 5

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

Hotel Riu Montego Bay - Adults Only - All Inclusive

Mahoe Bay, Ironshore Montego Bay Saint James

Get rates

Book a stay at this 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 Rose Hall Great House are located nearby.

Pool

Hot tub

Serenade Punta Cana Beach & Spa Resort - All Inclusive

Carretera Cabeza de Toro Punta Cana La Altagracia

CA $449

per night

Jan 26 - Jan 27

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 Cabeza de Toro Beach are located nearby.

On private beach

Pool

Ocean Eden Bay - Adults Only - All inclusive

Mountain Spring Bay, Coral Spring Falmouth

CA $696

per night

Jan 25 - Jan 26

Book a stay at this luxury property in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Burwood Beach and Blue Waters Beach Club 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, 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 $1,927. 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.