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Caribbean Islands flight + hotel packages
Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
per person
May 5 - May 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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
Save 100% on your flight
per person
Jun. 19 - Jun. 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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 Orient Bay Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
per person
Jun. 19 - Jun. 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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.

La Playa Orient Bay
Save 100% on your flight
per person
Jun. 19 - Jun. 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Philipsburg (SXM)
Stay at this 4-star 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 Beach and Grand Case Beach are located nearby.

Holland House Beach Hotel
Save 100% on your flight
per person
Jun. 19 - Jun. 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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.
Top Caribbean Islands hotels deals

Serenade Punta Cana Beach & Spa Resort - All Inclusive
Carretera Cabeza de Toro, Punta Cana, La Altagracia
Free cancellation
Reserve now, pay when you stay
The price is CA $382 per night
CA $382
CA $451 total
includes taxes & fees
Apr 29 - Apr 30
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

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro, Higuey, Punta Cana, La Altagracia
The price is CA $574 per night
CA $574
CA $677 total
includes taxes & fees
Apr 28 - Apr 29
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

Caribe Hilton
1 San Geronimo Street, San Juan
Free cancellation
Reserve now, pay when you stay
The price is CA $365 per night
CA $365
CA $476 total
includes taxes & fees
Apr 29 - Apr 30
Book a stay at this beach resort in San Juan. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Condado Beach and Pan American Pier are located nearby.
Pool
Hot tub

Hotel Riu Montego Bay - Adults Only - All Inclusive
Mahoe Bay, Ironshore, Montego Bay, Saint James
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

Grand Hyatt Baha Mar
One Baha Mar Boulevard, Nassau, New Providence
Free cancellation
Reserve now, pay when you stay
The price is CA $455 per night
CA $455
CA $698 total
includes taxes & fees
Apr 28 - Apr 29
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

Ocean Blue & Sand Beach Resort - All Inclusive
Car. Arena Gorda, Playa Bavaro, Punta Cana, La Altagracia
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 restaurant in our reviews. Popular attractions Bavaro Beach and Iberostar Golf Course are located nearby.
On private beach
Pool
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View all propertiesLowest 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 and enjoy its seafood restaurants.
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