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.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

per person

Jun. 23 - Jun. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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. 23 - Jun. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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 breakfast and the pool in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Sea Palace by Capital Vacations

Save 100% on your flight

per person

Aug. 1 - Aug. 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

Stay at this 3-star beach aparthotel in Philipsburg. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Maho Beach and Orient Bay Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

per person

Jun. 23 - Jun. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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 Dawn Beach are located nearby.

Oceans at Divi Little Bay

per person

Jun. 23 - Jun. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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 Mullet Bay Beach are located nearby.

La Playa Orient Bay

per person

Jun. 23 - Jun. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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 helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Green Cay 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 $818 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

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $225

per night

Jun. 11 - Jun. 12

Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free cancellation

Reserve now, pay when you stay

CA $156

per night

Jun. 1 - Jun. 2

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.

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 $155

per night

Jun. 22 - Jun. 23

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 restaurant in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

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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.