Caribbean Islands Vacations 2025/2026 from CA $1,439

Caribbean Islands flight + hotel packages

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

Panorama Residences at Monte Vista

Point Blanche

CA $1,439

per person

Dec 12 - Dec 19

found 10 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

Stay at this 4-star aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Orient Bay Beach and Maho Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,595

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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

CA $3,003

per person

Jan 10 - Jan 17

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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 Orient Bay Beach and Maho Beach are located nearby.

Holland House Beach Hotel

Downtown Philipsburg

CA $1,731

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,443

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) 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 Grand Case 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 $440

CA $677 total

Oct 29 - Oct 30

includes taxes & fees

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 Junkanoo Beach are located nearby.

Pool

Spa

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 $470

CA $602 total

Oct 29 - Oct 30

includes taxes & fees

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

Hyatt Vacation Club at Hacienda del Mar, Dorado

301 Hwy 693, Dorado, Vega Alta

Free cancellation

CA $249

CA $332 total

Nov 18 - Nov 19

includes taxes & fees

Stay at this 3.5-star 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

Serenade Punta Cana Beach & Spa Resort - All Inclusive

Carretera Cabeza de Toro, Punta Cana, La Altagracia

CA $276

CA $353 total

Oct 29 - Oct 30

includes taxes & fees

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.

On private beach

Pool

Holiday Inn Resort Aruba - Beach Resort & Casino by IHG

J E Irausquin Boulevard 230, Noord

Free cancellation

CA $393

CA $515 total

Nov 4 - Nov 5

includes taxes & fees

Stay at this 4-star beach resort in Noord. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Eagle Beach and Hyatt Regency Casino are located nearby.

Pool

Spa

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 Rose Hall Great House are located nearby.

Pool

Hot tub

Don't see what you're looking for?

See all available properties in Caribbean Islands

View all properties

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 $1,439. 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.