Caribbean Islands Vacations 2026 from CA $1,223

Caribbean Islands flight + hotel packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,223

per person

May 19 - May 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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.

The Villas at Simpson Bay Resort

Pelican Key

CA $2,244

per person

Apr 11 - Apr 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) 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 $2,136

per person

Apr 11 - Apr 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) 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 Grand Case Beach and Dawn Beach are located nearby.

Oyster Bay Beach Resort

Oyster Pond

CA $1,877

per person

Apr 11 - Apr 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

Book a stay at this beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grand Case Beach and Oyster Bay Marina are located nearby.

Holland House Beach Hotel

Downtown Philipsburg

CA $2,740

per person

Apr 11 - Apr 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) 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 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

CA $668

CA $951 total

Mar 24 - Mar 25

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 Junkanoo Beach are located nearby.

Pool

Spa

Serenade Punta Cana Beach & Spa Resort - All Inclusive

Carretera Cabeza de Toro Punta Cana La Altagracia

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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

Hotel Riu Republica - Adults only - All Inclusive

Playa Arena Gorda Punta Cana

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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 Arena Gorda Beach and Macao Beach are located nearby.

Pool

Hot tub

Ocean Blue & Sand Beach Resort - All Inclusive

Car. Arena Gorda Punta Cana La Altagracia

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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 Bavaro Beach are located nearby.

On private beach

Pool

Hotel Riu Montego Bay - Adults Only - All Inclusive

Mahoe Bay, Ironshore Montego Bay Saint James

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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

Renaissance Wind Creek Aruba Resort

L G Smith Boulevard 82 Oranjestad

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Book a stay at this luxury resort in Oranjestad. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Eagle Beach and Renaissance Mall Aruba 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 $1,223. 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.