Book Exclusive Caribbean Islands Vacation Packages

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Caribbean Islands flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Maho
Price was CA $1,288, price is now CA $864 per person
CA $864
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this beach resort in Lowlands. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,305, price is now CA $1,292 per person
CA $1,292
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip 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

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $2,382, price is now CA $1,139 per person
CA $1,139
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $1,511, price is now CA $943 per person
CA $943
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orient Bay and Grand Case Beach are located nearby.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was CA $4,738, price is now CA $3,160 per person
CA $3,160
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 Port of St. Maarten are located nearby.

Top Caribbean Islands hotels deals

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
One Baha Mar Boulevard Nassau New Providence
Free cancellation
Reserve now, pay when you stay
The price is CA $311 per night
CA $311
CA $522 total
Sep 27 - Sep 28
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 Aquaventure are located nearby.
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

5 out of 5
Playas de Bavaro Punta Cana La Altagracia
The price is CA $413 per night
CA $413
CA $528 total
Oct 8 - Oct 9
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 Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
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
Barceló Bávaro Palace - All Inclusive

Barceló Bávaro Palace - All Inclusive

4.5 out of 5
Carretera Bávaro Km. 1 Punta Cana La Altagracia
The price is CA $300 per night
CA $300
CA $385 total
Oct 4 - Oct 5
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.
On private beach
Pool
Wyndham Alltra Punta Cana All-Inclusive Resort

Wyndham Alltra Punta Cana All-Inclusive Resort

4 out of 5
Playas Uvero Alto Punta Cana La Altagracia
Free cancellation
Reserve now, pay when you stay
The price is CA $203 per night
CA $203
CA $203 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this beach resort in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Macao Beach and Sirenis Aquagames Water Park are located nearby.
Pool
Breakfast included
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
301 Hwy 693 Vega Alta
Free cancellation
The price is CA $175 per night
CA $175
CA $251 total
Sep 30 - Oct 1
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.

Stay near popular Caribbean Islands attractions

A beach scene with a flag, beach chairs, umbrellas, and a vendor cart.

Eagle Beach

9.4/10 (6,014 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.
See properties

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 $864. 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.

Photos of local treasures

Browse Caribbean Islands vacation photos for more inspiration

A beach with clear turquoise water, white sand, and palm trees.
A wooden pier leading to a cruise ship docked at a clear turquoise sea under a partly cloudy sky.
A beach with clear turquoise water, white sand, and palm trees.
A beach with clear turquoise water, a palm tree, and red stockings hanging from it.
A rocky coastline with waves crashing against the shore, surrounded by dense tropical foliage.