Simpson Bay Vacation Packages 2026 from $924

Name: Hilton Vacation Club Royal Palm St. Maarten
Price range: $177 total

Simpson Bay flight + hotel vacation packages

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

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

$924

per person

Dec 17 - Dec 21

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.

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,118

per person

Nov 23 - Nov 30

found 14 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.

The Villas at Simpson Bay Resort

Pelican Key

$1,155

per person

Dec 17 - Dec 21

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.

Panorama Residences at Monte Vista

Point Blanche

$1,058

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop 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.

Holland House Beach Hotel

Downtown Philipsburg

$1,439

per person

Dec 17 - Dec 21

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.

Top Simpson Bay hotels deals

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$183 nightly

$191 total

Oct 12 - Oct 13

Total with taxes and fees

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$449 nightly

$471 total

Oct 21 - Oct 22

Total with taxes and fees

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.

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$206 nightly

$215 total

Oct 4 - Oct 5

Total with taxes and fees

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$155 total

Sep 29 - Sep 30

Total with taxes and fees

This resort features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and laundry facilities are also on offer.

The Atrium Beach Resort and Spa, an Ascend Collection Resort

6 Billy Folly Road Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$133 total

Oct 4 - Oct 5

Total with taxes and fees

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.

Hilton Vacation Club Royal Palm St. Maarten

115 Welfare Road Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$177 total

Oct 4 - Oct 5

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

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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.

Stay near popular Simpson Bay attractions

A wooden pier extending into calm waters with sailboats anchored nearby.

Kim Sha Beach

8.8/10 (591 reviews)

Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and top-notch restaurants in this romantic area.

See properties

Frequently asked questions

How much are vacation packages to Simpson Bay?

With a Travelocity vacation package, you could live it up in Simpson Bay for as low as $924. Activities, hotels and flights — we're a one-stop shop for all of them. You'll save a bunch just by combining your bookings together. And with all that taken care of before you go, you won't have a care in the world.

How long should my Simpson Bay vacation be?

Around 5 nights is the average time frame visitors vacation in Simpson Bay. But how long is right for you comes down to how many treasured memories you want to make. Why not allow a little more time and explore some hidden treasures?

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

Your dream escape is waiting for you at Travelocity. With access to 400 airlines and 1,000,000 hotels all over the world, selecting the perfect Simpson Bay package deal couldn't be easier.

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

Nothing tops the satisfaction of knowing you've bagged the best deal available — that's our Price Match Guarantee. Add to that our impressive range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a hassle-free vacation.

Can I save on my Simpson Bay car rental if I book it with hotels and flights?

You most certainly can — bundle your car, flight and hotel into a Simpson Bay vacation package and you'll save loads. With so many things to do in the Simpson Bay area, that rental vehicle will make exploring a breeze. Once you're in the driver's seat, put the stereo on and head to Dickenson Bay Beach, a renowned sight about 100 mi from Simpson Bay.

Which airport is best for Simpson Bay?

For many, a stay in Simpson Bay means a visit to Princess Juliana Intl. Airport (SXM). This busy airport sits 1 mi west of the downtown area. You could also opt to fly into Robert L. Bradshaw Intl. Airport (SKB) (55 mi away from central Simpson Bay) or Clayton J. Lloyd Intl. Airport (AXA) (12 mi away from central Simpson Bay).

What is there to do in Simpson Bay?

There's a certain magic as you roam the streets of Simpson Bay. Simpson Bay Beach and Flamingo Beach are just two renowned sights that entice visitors to this wonderful city, so put them at the top of your travel itinerary.

Where should I stay when visiting Simpson Bay?

If you're searching for a place to lay your head, take a look at the Hilton Vacation Club Flamingo Beach St. Maarten. It's the top pick for many visitors.