Happy Bay Vacation Deals: Happy Bay, Grand Case Vacations

Happy Bay vacation package deals

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

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Jul 20 - Jul 27

Roundtrip flight included

Newark (EWR) 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 playground, and barbecue grills are available on site.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

per person

Jun 2 - Jun 6

Roundtrip flight included

Newark (EWR) 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 waterslide, and barbecue grills are available on site.

La Playa Orient Bay

per person

Jun 2 - Jun 6

Roundtrip flight included

Newark (EWR) to Philipsburg (SXM)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Families will appreciate the onsite laundry facilities and babysitting.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

per person

Jun 2 - Jun 6

Roundtrip flight included

Newark (EWR) 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.

Sea Palace by Capital Vacations

per person

Jun 2 - Jun 6

Roundtrip flight included

Newark (EWR) to Philipsburg (SXM)

A restaurant, self parking, and a 24-hour front desk are among this aparthotel's amenities. A snack bar/deli is also provided.

Holland House Beach Hotel

per person

Jul 20 - Jul 27

Roundtrip flight included

Newark (EWR) 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.

Frequently asked questions

How much are vacation packages to Happy Bay?

Save a tidy sum on your visit to Happy Bay by combining your flights and hotel into a $711 package. With all that extra cash jangling around in your pocket, why not stay for another night or two and discover even more?

Where can I get the best vacation package deals for Happy Bay?

It’s simple — head to Travelocity. With as many as 400 air carriers and 1,000,000 worldwide properties, it’s a breeze to find a Happy Bay package deal that fits your budget.

Why should I purchase my Happy Bay vacation package with Travelocity?

We offer round-the-clock support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have amazing destinations for you to journey to all across the globe. Wander with us and make your hip pocket happy.

Top Happy Bay hotel deals

4 BEDROOM VILLA, MAGNIFICENT SEA VIEW, BEACH ON FOOT

This villa features an outdoor pool and a spa tub. A garden is also provided.

Lovely room in a nice villa with a big garden, close to Friars bay beach

$70

per night

May 7 - May 8

A garden is available at this vacation home.

Villa Picaflor Friars Bay

An outdoor pool is featured at this villa, along with a garden and barbecue grills.

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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.