Hollywood Casino Vacation Deals: Hollywood Casino, Pelican Key Holidays

Hollywood Casino vacation package deals

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

Cupecoy Beach Club

Maho

per person

Jun. 19 - Jun. 26

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Philipsburg (SXM)

Stay at this 3-star beach aparthotel in Lowlands. Enjoy a beach locale, furnished balconies, and an in-room coffeemaker. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

May 25 - May 31

found 12 hours 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.

Oceans at Divi Little Bay

Save 100% on your flight

per person

May 26 - Jun. 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

Stay at this 4-star 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 Orient Bay Beach are located nearby.

Coral Beach Club Villas & Marina

Oyster Pond

Save 100% on your flight

per person

May 26 - Jun. 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

Stay at this 4-star 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.

Aura

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 vacation home in Anse Marcel. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Villa Amalia

Save 100% on your flight

per person

Jun. 4 - Jun. 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

Stay at this 5-star 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.

Frequently asked questions

How much are vacation packages to Hollywood Casino?

Let Travelocity take all the stress out of organizing your next big trip to Hollywood Casino. Book our awesome CA $1,761 package deal and save both money and time. With your hotel and flights sorted, you can concentrate on the fun parts of your adventure — like visiting those must-do attractions!

Where can I get the best vacation package deals for Hollywood Casino?

Travelocity has endless ways to score an awesome Hollywood Casino package deal. Select from as many as 400 partner airlines and 665,000 properties around the globe and craft a vacation package that’s suited to you. With almost endless choice, it’s time to start planning your next big adventure.

Why should I purchase my Hollywood Casino vacation package with Travelocity?

By booking your flights, hotel, activities and car rental altogether, you’ll save time and money. We have a dedicated team of experts available 24/7, and you’ll know that you’re always getting the lowest price possible with our Price Match Guarantee. So, what’s stopping you? Book the vacation of your dreams today and get packing!

Can I go on vacation to Hollywood Casino at this time?

We have the local knowledge to help make your vacation dreams come true, so before arranging your trip to Hollywood Casino, take a look at our Covid-19 Travel Advisor. Here you’ll discover up-to-date info on quarantine policies, travel restrictions and much more.

Top Hollywood Casino hotel deals

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $207

CA $249 total

includes taxes & fees

Apr 29 - Apr 30

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.

On private beach

Pool

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $208

CA $256 total

includes taxes & fees

May 4 - May 5

Stay at this 3.5-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Pool

Parking included

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $250

CA $301 total

includes taxes & fees

May 5 - May 6

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.

Pool

Parking included

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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.