Orient Bay Vacation Packages 2026 from $766

Orient Bay flight + hotel vacation packages

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

The Villas at Simpson Bay Resort

Pelican Key

$766

per person

Dec 1 - Dec 5

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.

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,103

per person

Nov 13 - Nov 20

found 17 hours 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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$1,431

per person

Dec 20 - Dec 26

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.

Panorama Residences at Monte Vista

Point Blanche

Save 100% on your flight

$1,695

per person

Dec 20 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

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.

The Atrium Beach Resort and Spa, an Ascend Collection Resort

Save 100% on your flight

$1,198

per person

Jan 1 - Jan 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

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.

Top Orient Bay hotels deals

Esmeralda Resort

B.P. 5141, Baie Orientale Orient Bay

Free Cancellation

Reserve now, pay when you stay

$251 nightly

$261 total

Oct 16 - Oct 17

Total with taxes and fees

This Colonial hotel features 14 outdoor pools and 4 beach bars. Families will appreciate the playground and onsite laundry facilities. Enjoy a meal from the restaurant and perks like free continental breakfast and free self parking.

Pool

Breakfast included

La Playa Orient Bay

116 Parc de la Baie Orientale Orient Bay

Free Cancellation

Reserve now, pay when you stay

$322 nightly

$336 total

Nov 2 - Nov 3

Total with taxes and fees

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.

Pool

Breakfast included

Hotel La Plantation

C5 Orient Bay Orient Bay

$175 nightly

$182 total

Oct 16 - Oct 17

Total with taxes and fees

This hotel's 3 restaurants, 3 bars/lounges, and outdoor pool are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport pick-up service. Relax with a drink at the poolside bar and enjoy free perks like self-serve breakfast and free self parking.

Pool

Breakfast included

La Villa Hibiscus

Rue de Mont Vernon Orient Bay Collectivity of Saint Martin

$179 nightly

$186 total

Oct 31 - Nov 1

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Enjoy the outdoor pool and conveniences like express check-out and concierge services.

Pool

Pet friendly

Palm Court Residence & Hotel at Orient Beach

Orient Beach Orient Bay

$247 nightly

$259 total

Nov 12 - Nov 13

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy free perks like continental breakfast and free self parking.

Pool

Breakfast included

Orient Beach Hotel

115 Vavina Bay Orient Bay

$224 nightly

$233 total

Oct 20 - Oct 21

Total with taxes and fees

This hotel features 5 restaurants and an outdoor pool. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.

Pool

Breakfast included

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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.

Frequently asked questions

How much are vacation packages to Orient Bay?

Your vacation fantasies can become a reality in Orient Bay from an impressive $766. Our package deals include flights and hotels, so organizing everything should be a breeze. All you'll have to concentrate on is having a good time.

How long should my Orient Bay vacation be?

Many people book a hotel for 6 nights in Orient Bay. But that doesn't necessarily mean you have to follow suit. How long you stick around depends on what sorts of things you want to do on your vacation. If you'd love to familiarize yourself with every part of this superb place, consider booking another night or two (or even longer!).

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

Picking up the best package deal to Orient Bay couldn't be easier with Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, you're spoiled for choice when it comes to selecting your hotels and flights.

Why should I book my Orient Bay vacation bundle with Travelocity?

Because we believe in creating stress-free travel experiences. From flights and hotels to car rentals and activities, everything is at your fingertips. Our customer care is available 24/7 to make sure your needs are taken care of. We also have a Price Match Guarantee, so you can book your trip knowing you've landed the best deal possible. Find a lower price and we'll match it!

Will I save money on my Orient Bay car rental if I book it with a hotel or flight?

Absolutely — bundle your car, hotel and flight into an Orient Bay vacation package and you can save a ton. With so much to uncover in and around Orient Bay, having your own set of wheels will make exploring a breeze. Once you've slid into the driver's seat, turn up the tunes and cruise toward Dickenson Bay Beach, a must-see attraction around 100 mi from Orient Bay.

Which airport is best for Orient Bay?

Princess Juliana Intl. Airport (SXM) is a major hub. You'll find it roughly 6 mi southwest of Orient Bay. Your other options are Robert L. Bradshaw Intl. Airport (SKB) (60 mi away from central Orient Bay) and Clayton J. Lloyd Intl. Airport (AXA) (8 mi away from central Orient Bay).

Where should I stay when visiting Orient Bay?

Many travelers check in to the Orient Beach Hotel. It's a terrific base for your Orient Bay getaway.