Hollywood Casino Vacation Deals: Hollywood Casino, Pelican Key Vacations

Hollywood Casino vacation package deals

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

Simpson Bay Resort, Marina & Spa

Pelican Key

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

This hotel features an outdoor pool and a 24-hour gym. Families will appreciate the waterslide, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.

Oyster Bay Beach Resort

Oyster Pond

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

This resort features a full-service spa, a marina, and 2 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and in-room childcare. Enjoy the outdoor pool and perks like free WiFi.

Holland House Beach Hotel

Downtown Philipsburg

Save 100% on your flight

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

A restaurant and a bar/lounge are featured at this hotel. Dine at the beachfront restaurant and relax with beach umbrellas. WiFi in public areas is free.

La Playa Orient Bay

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Relax with a drink at the beach bar and enjoy free perks like English breakfast and free self parking.

Frequently asked questions

How much are vacation packages to Hollywood Casino?

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

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Top Hollywood Casino hotel deals

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$123 total

Aug 31 - Sep 1

Total includes taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.

Hilton Vacation Club Flamingo Beach St. Maarten

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

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$152 total

Aug 17 - Aug 18

Total includes taxes and fees

This resort features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and laundry facilities are also on offer.

The Atrium Beach Resort and Spa, Ascend Hotel Collection

6 Billy Folly Road, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$124 total

Aug 21 - Aug 22

Total includes taxes and fees

A full-service spa and an outdoor pool are featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A business center, a terrace, and a grocery/convenience store are also on offer.

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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.