Upper Prince's Quarter Vacation Packages 2026 from $927

Upper Prince's Quarter flight + hotel vacation packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

$927

per person

Apr 1 - Apr 5

found 1 day ago

Roundtrip non-stop 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

Pelican Key

Save 100% on your flight

$1,325

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip 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.

The Morgan Resort Spa Village

Save 100% on your flight

$1,347

per person

Mar 27 - Apr 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

A full-service spa, an outdoor pool, and a restaurant are all featured at this resort. Enjoy the gym and perks like free valet parking and a free airport shuttle. There's a bar/lounge on site, and concierge services and free newspapers are also provided.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

$1,031

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip 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.

La Playa Orient Bay

$1,156

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 in-room childcare.

Top Upper Prince's Quarter hotels deals

Oyster Bay Beach Resort

10 Emerald Merit Rd Oyster Pond

$300 nightly

$313 total

Mar 1 - Mar 2

Total with taxes and fees

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.

Pool

Hot Tub

JW Marriott St. Maarten Beach Resort & Spa

144 Oyster Pond Resort Oyster Pond Sint Maarten

$817 nightly

$854 total

Feb 10 - Feb 11

Total with taxes and fees

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Pool

Spa

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond Road No 156 Oyster Pond

Free Cancellation

Reserve now, pay when you stay

Get rates

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.

Pool

Spa

Panorama Residences at Monte Vista

Kitty Drive #6 Philipsburg Sint Maarten

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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

Dawn Beach Club Resort Sint Maarten

144 Oyster Pond Rd Oyster Pond Sint Maarten

Free Cancellation

Reserve now, pay when you stay

Get rates

This smoke-free condo resort includes 2 restaurants, an outdoor pool, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy perks like free self parking. A snack bar/deli, WiFi in public areas, and concierge services are also on offer.

Pool

Kitchen

Coral Beach Club Villas & Marina

Emerald Merit Road #3 Oyster Pond

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This Mediterranean resort features a full-service spa, a marina, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare.

Pool

Spa

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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.

Captain Hodge Pier in Philipsburg, Saint Martin, Caribbean

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.

Fort Amsterdam

2/5(2 reviews)

You can find out about the history of Little Bay with a stop at Fort Amsterdam. Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Upper Prince's Quarter?

With Travelocity vacation packages, you could paint the town red in Upper Prince's Quarter for a mere $927. Flights, hotels and tours — we've got you. You'll save a bunch just for bundling your bookings. And with all that taken care of before you set off, you don't have to worry about a thing.

Where can I get the best vacation package deals for Upper Prince's Quarter?

Look no further than Travelocity. With no less than 400 air carriers and 1,000,000 worldwide properties, it's easy to craft an Upper Prince's Quarter package deal that appeals to your wanderlust.

Why should I book my Upper Prince's Quarter vacation bundle via Travelocity?

With fantastic service, support available 24/7 and some of the most gorgeous getaways around, you'll never roam alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.

Will I save money on my Upper Prince's Quarter car rental if I book it with my hotel or flight?

Booking an Upper Prince's Quarter vacation package with Travelocity is a simple way to save your hard-earned money. Pick a car, hotel and flight, or any combination of them, and land awesome discounts. You might also want to add in some experiences. After you've collected the keys to your rental car, venture out of the neighborhood and discover what the area has to offer. Roughly 100 mi from Upper Prince's Quarter, Dickenson Bay Beach is well worth a road trip.

What is there to do in Upper Prince's Quarter?

Guana Bay Beach is a fantastic place to begin your sightseeing adventures. Don't forget your comfy sneakers, because this neighborhood will keep you on the go.