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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

Jun. 26 - Jul. 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Jun. 8 - Jun. 15

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 Orient Bay Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

per person

Jun. 8 - Jun. 15

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.

La Playa Orient Bay

Save 100% on your flight

per person

Jun. 26 - Jul. 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

Divi Little Bay Beach Resort

Save 100% on your flight

per person

Jun. 11 - Jun. 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

Stay at this 4-star beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.

Holland House Beach Hotel

Save 100% on your flight

per person

Jun. 26 - Jul. 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

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 $1,200 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

CA $166

CA $199 total

includes taxes & fees

May 15 - May 16

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 $157

CA $201 total

includes taxes & fees

Apr 23 - Apr 24

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 $211

CA $254 total

includes taxes & fees

May 18 - May 19

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

Don't see what you're looking for?

See all available properties in Hollywood Casino

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.