Simpson Bay Vacation Packages 2025/2026 from $824

Name: Hilton Vacation Club Royal Palm St. Maarten
Price range: $237 total

Simpson Bay flight + hotel vacation packages

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

Simpson Bay Resort, Marina & Spa

Pelican Key

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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

Save 100% on your flight

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

Oyster Bay Beach Resort

Oyster Pond

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

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.

Holland House Beach Hotel

Downtown Philipsburg

Save 100% on your flight

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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

$118 nightly

$123 total

Aug 31 - Sep 1

Total includes taxes and fees

On private beach

Pool

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$262 nightly

$272 total

Aug 26 - Aug 27

Total includes 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.

Pool

Spa

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$152 total

Aug 17 - Aug 18

Total includes 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.

Pool

Parking included

The Atrium Beach Resort and Spa, Ascend Hotel Collection

6 Billy Folly Road, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$124 total

Aug 21 - Aug 22

Total includes 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.

Pool

Spa

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$160 total

Sep 14 - Sep 15

Total includes taxes and fees

Pool

Parking included

Hilton Vacation Club Royal Palm St. Maarten

115 Welfare Road, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$226 nightly

$237 total

Sep 2 - Sep 3

Total includes 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.

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

Kim Sha Beach

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.

Hollywood Casino

Why not roll the dice with a visit to Hollywood Casino during your visit to Simpson Bay? Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

Simpson Bay Beach

Why not spend a lazy afternoon at Simpson Bay Beach during your trip to Simpson Bay? Check out the shops and lively bars in this romantic area.

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 $824. 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.