Oyster Pond Vacation Packages 2025/2026 from $825

Oyster Pond flight + hotel vacation packages

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

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$825

per person

Nov 15 - Nov 22

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.

The Villas at Simpson Bay Resort

Save 100% on your flight

$920

per person

Nov 15 - Nov 22

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

Save 100% on your flight

$1,492

per person

Nov 22 - Nov 29

found 13 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.

Holland House Beach Hotel

Downtown Philipsburg

Save 100% on your flight

$981

per person

Nov 15 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

Save 100% on your flight

$1,227

per person

Nov 15 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Top Oyster Pond hotels deals

Oyster Bay Beach Resort

10 Emerald Merit Rd, Oyster Pond

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$197 total

Sep 2 - Sep 3

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, Building A, Oyster Pond, Sint Maarten

$319 nightly

$336 total

Sep 2 - Sep 3

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, Dawn Beach, Oyster Pond

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$134 total

Sep 2 - Sep 3

Total with taxes and fees

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

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

Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR

Get rates

A gym is featured at this villa, along with laundry facilities and concierge services. Families will appreciate the arcade/game room and barbecue grills.

Pool

Kitchen

LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

Get rates

This villa features an outdoor pool and a gym. A garden, laundry facilities, and concierge services are also on offer.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Oyster Pond

View all properties

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

Dawn Beach

Why not spend a carefree afternoon at Dawn Beach during your travels in Oyster Pond? Stroll along the seaside in this relaxing area, or check out its top-notch restaurants.

Oyster Bay Marina

Explore the waterfront in Oyster Pond with a trip to Oyster Bay Marina. Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

Coralita Beach

Why not spend a lazy afternoon at Coralita Beach during your trip to Oyster Pond? Wander the beautiful beaches and seaside in this romantic area.

Frequently asked questions

How much are vacation packages to Oyster Pond?

Your vacation fantasies can become reality in Oyster Pond for only $825. Package deals include flights and hotels, and they'll make booking your trip nice and easy. The only thing you'll have to focus on is having a good time.

How long should my Oyster Pond vacation be?

Most travelers choose to spend roughly 5 nights in Oyster Pond, but how long you stay is your call. If you're eager to discover all the exciting things this place offers, why not hang around another few nights?

Where can I get the best vacation package deals for Oyster Pond?

You can score sensational Oyster Pond package deals with Travelocity. Pick and choose from as many as 400 airlines and 1,000,000 properties worldwide and turn those travel fantasies into reality.

Why should I book my Oyster Pond vacation package with Travelocity?

You'll not only enjoy great savings, but you'll also have access to our 24/7 customer support, high-quality service and a Price Match Guarantee. Journey across the globe, discover hidden gems and forge long-lasting memories — we'll take care of the little details.

Can I save on my Oyster Pond car rental if I bundle it with hotels and flights?

With an Oyster Pond vacation package, you can combine your hotel, car and flight bookings and save a nice amount. If you want to explore the best of this exciting region, why not check out Dickenson Bay Beach? This must-see sight is 100 mi from Oyster Pond. With your own set of wheels, you'll be there soon enough.

Which airport is best for Oyster Pond?

Princess Juliana Intl. Airport (SXM) is one of the top airports for Oyster Pond. It's situated 6 mi west of the city center. Other choices include Robert L. Bradshaw Intl. Airport (SKB) (55 mi away from central Oyster Pond) and Clayton J. Lloyd Intl. Airport (AXA) (11 mi away from central Oyster Pond).

What is there to do in Oyster Pond?

Gibb's Bay Beach is just one of the amazing sights that make Oyster Pond such a popular destination. But allow some extra time to explore its lesser-known attractions too. This is often where the best memories are made.

Where should I stay when visiting Oyster Pond?

Many visitors choose to spend their nights at the Princess Heights Luxury Boutique Condo Hotel. It's sure to be a great base for your Oyster Pond getaway.