Philipsburg Vacation Packages 2026 from $778

Philipsburg flight + hotel vacation packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

$778

per person

Mar 19 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

$1,172

per person

Mar 7 - Mar 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

$795

per person

Jan 30 - Feb 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Oceans at Divi Little Bay

Save 100% on your flight

$1,220

per person

Mar 7 - Mar 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

This hotel's 4 restaurants and 3 outdoor pools are some of the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning, luggage storage, and concierge services are also on offer.

Divi Little Bay Beach Resort

Save 100% on your flight

$1,146

per person

Mar 7 - Mar 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this resort. Relax with free beach cabanas, sun loungers, and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Top Philipsburg hotels deals

Divi Little Bay Beach Resort

Little Bay Road Philipsburg

Free Cancellation

Reserve now, pay when you stay

$525 nightly

$551 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Pool

All inclusive

Seaview Beach Hotel

#85C Front Street Philipsburg

$131 nightly

$137 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and an outdoor pool. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at the poolside bar and enjoy perks like free WiFi.

Pool

Spa

Oceans at Divi Little Bay

Little Bay Road Philipsburg St. Maarten

Free Cancellation

Reserve now, pay when you stay

$572 nightly

$601 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Pool

All inclusive

The Paradise Inn

Senna road # 7 Philipsburg

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$79 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A snack bar/deli and a convenience store are also provided.

Pool

Parking included

July Apartments

A.T. Illidge Road 117 Philipsburg

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$80 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, luggage storage, and laundry facilities are also on offer.

Kitchen

Parking included

Panorama Residences at Monte Vista

Kitty Drive #6 Philipsburg Sint Maarten

Get rates

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a virtual front desk are also on offer.

Pool

Kitchen

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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.

Popular places to visit

Great Bay Beach

4.5/5(88 reviews)

If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area.

Philipsburg Boardwalk

Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.

Guana Bay Beach

4/5(9 reviews)

If a restful vacation is part of your travel plans, Guana Bay Beach might be the perfect place to seek out during your trip to Upper Prince's Quarter.

Frequently asked questions

How much are vacation packages to Philipsburg?

Your travel daydreams can become reality in Philipsburg from as little as $778. Our packages include flights and hotels, so they're bound to make booking a cinch. All you'll have to focus on is having a good time.

How long should my Philipsburg vacation be?

The majority of people lock in their hotel for 5 nights in Philipsburg. But that doesn't necessarily mean you have to do that. How long you spend here depends on what you plan to do on your vacation. If you'd like to explore every nook and cranny of this incredible location, book another few nights (or even an extra week!).

Where can I get the best vacation package deals for Philipsburg?

For an excellent package deal to Philipsburg, nothing compares to Travelocity. Take your pick from as many as 400 airlines and 1,000,000 properties around the globe to create your ideal escape — it's really that simple.

Why should I book my Philipsburg vacation package via Travelocity?

Because you'll never roam alone if you secure your trip through us, and we offer round-the-clock customer support and excellent service to boot. Add to that our Price Match Guarantee and tons of experiences and destinations to choose from. We're here to help you jet off on the vacation of a lifetime.

Can I save on my Philipsburg car rental if I combine it with hotels and flights?

With a Philipsburg vacation package, you can combine your car, flight and hotel bookings and save loads. If you're in the mood to uncover the best of this impressive destination, why not make a beeline for Dickenson Bay Beach? This must-see attraction is 100 mi from Philipsburg. With your own rental car, you'll be there in a jiffy.

Which airport is best for Philipsburg?

For many, heading to Philipsburg means going through Princess Juliana Intl. Airport (SXM). This popular airport is located 4 mi west of the city center. You could also choose to fly into Robert L. Bradshaw Intl. Airport (SKB) (55 mi away from central Philipsburg) or Clayton J. Lloyd Intl. Airport (AXA) (12 mi away from central Philipsburg).

What is there to do in Philipsburg?

Philipsburg is teeming with sights to check out, such as Little Bay Beach and Sint Maarten Park. These well-known attractions are on most visitors' must-see lists.

Where should I stay when visiting Philipsburg?

The Princess Heights Luxury Boutique Condo Hotel is the number one choice of many visitors. Book now to avoid missing out.