Simpson Bay Vacations from $946

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Your Simpson Bay Vacation

With a vacation package to Simpson Bay, all the organizing is done beforehand. This gives you a lot more time to discover some of the features that define this beachfront city, such as its lively atmosphere, beaches and cosmopolitan vibe. If sightseeing is on the to-do list during your trip to Simpson Bay, check out leading attractions like Maho Beach, Marigot Market and Fort St. Louis. Don't delay visiting this destination any longer. Your dream Simpson Bay vacation is a couple of clicks away with Expedia.

The Latest Simpson Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
$946
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
Save 100% on your flight
$1,481
per person
Jan 6 - Jan 11
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$1,622
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Will be be back

Reviewed on Oct 17, 2026

The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

Save 100% on your flight
$1,843
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Great time

Reviewed on Oct 20, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

Save 100% on your flight
$1,543
per person
Dec 10 - Dec 15
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
9/10 Wonderful! (2,412 reviews)
The Morgan hotel nice I enjoyed my stay there, the staff was polite and helpful. I had the most beautiful view from my room. The property was big and had lots of amenities o keep me occupied. Definitely will be back

Reviewed on Oct 20, 2026

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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)
Kim Sha Beach offers pristine white sands and turquoise waters ideal for families and water sports enthusiasts. Enjoy jet skiing or kayaking, then explore the vibrant restaurants and nightlife of nearby Simpson Bay.
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A Hollywood Casino building with a red roof, yellow walls, and a signboard.

Hollywood Casino

8.2/10 (583 reviews)
Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.
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Simpson Bay Beach

9.2/10 (1,834 reviews)
Simpson Bay Beach offers pristine white sand and tranquil waters along one of Sint Maarten's longest shorelines. Enjoy peaceful sunbathing or swimming, with nearby beach bars for refreshments.
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Flamingo Beach

9.0/10 (768 reviews)
Pristine white sands and turquoise waters define this quintessential Caribbean escape in Simpson Bay. Enjoy swimming in gentle waves or snorkeling the clear waters before watching a spectacular sunset.
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Lay Bay Beach

8.4/10 (212 reviews)
Lay Bay Beach offers a tranquil escape between Simpson Bay and Maho on Sint Maarten's Dutch side. Bring your own supplies to this serene, undeveloped stretch of sand for genuine beachside peace.
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Dunes Casino

8.0/10 (249 reviews)
This relaxed casino offers over 200 slot machines and electronic games in a laid-back atmosphere. Enjoy the sportsbook lounge with flat-screen TVs while placing bets in this intimate gaming venue.
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Market Garden Supermarket

9.4/10 (8 reviews)
You can find the perfect gifts to bring home at Market Garden Supermarket during your stay in Simpson Bay. Check out the shops and top-notch restaurants in this romantic area.
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What to do in Simpson Bay

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

$65
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

$159
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

$77
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
See all activities in Simpson Bay

Simpson Bay Hotel Deals

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
$198 nightly
$207 total
Oct 21 - Oct 22
Total with taxes and fees
Simpson Bay Resort, Marina & Spa
The Morgan Resort Spa Village

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$503 nightly
$528 total
Nov 20 - Nov 21
Total with taxes and fees
9/10 Wonderful! (2,427 reviews)
"The Morgan hotel nice I enjoyed my stay there, the staff was polite and helpful. I had the most beautiful view from my room. The property was big and had lots of amenities o keep me occupied. Definitely will be back"

Reviewed on Oct 20, 2026

The Morgan Resort Spa Village
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
Fully refundableReserve now, pay when you stay
$135 nightly
$142 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (1,800 reviews)
"Naomi was by far the best staff. She was very sweet & on top of everything. Room was nice. Able to section off from livingroom. Outdoor pool and grill area was nice. Balcony’s are nice. Smoking should be allowed outdoor on balcony."

Reviewed on Oct 19, 2026

Hilton Vacation Club Flamingo Beach St. Maarten
See all 428 properties in Simpson Bay
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.

Find the Best Simpson Bay Vacation Packages

Simpson Bay Beach Vacation

There's nothing like a Simpson Bay vacation to put a spring in your step. The soothing sound of rolling surf and the smell of salty sea air are sure to rejuvenate your mind and body. To be close to the city center on your trip to Simpson Bay, find a hotel around Simpson Bay Beach (just 1 mile away). If you're planning to stay for a while, take a peek at our Simpson Bay vacation deals. Not only will you be able to save cash, you'll also have other amazing beaches near you to explore, like Kim Sha Beach and Lay Bay Beach.

Things You Should Know About Simpson Bay

  • Why not think about Simpson Bay beach hotels for your next vacation? See what's available — there's nothing like staying at just minutes from the water.
  • If your idea of an amazing beach vacation involves staying in one of our villas, Cocovaa or The Morgan Resort & Spa will suit you perfectly.

Simpson Bay Essential Information

Language
Dutch
Currency
Netherlands Antillean guilders
Local Welcome
Hallo
Local Goodbye
Dag
Closest Airport
Princess Juliana Intl. Airport (SXM)
Max Temp Winter
80ºF
Max Temp Summer
80ºF
Top Sights
Maho Beach, Mullet Bay Beach and Cupecoy Beach

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Frequently asked questions

What types of vacation packages are available in Simpson Bay?
Simpson Bay, Sint Maarten, is primarily a beach destination, and vacation packages can be tailored to several travel styles:
  • Beach package: Many hotels offer ocean views, including The Villas at Simpson Bay Resort, a 4-star property rated 8.5 out of 10 by travelers, which is about 2 miles from Maho Beach.
  • Family-friendly package: Resorts like Simpson Bay Resort, Marina & Spa, a 4-star property rated 8.1 out of 10 by travelers, feature family rooms, outdoor pools, and playgrounds, making them ideal for stays with children.
  • Budget package: For value-conscious travelers, Baker's Suites, a 3.5-star hotel rated 8.7 out of 10 by travelers, offers amenities like free WiFi and kitchen facilities.
  • Luxury package: Some hotels in Simpson Bay cater to luxury travelers, such as The Morgan Resort Spa Village, a 4-star property rated 8.1 out of 10 by travelers, which includes a spa and outdoor pool.
  • Romantic package: Couples can find packages at properties like Mary's Boon Beach Resort & Spa, rated 8 out of 10 by travelers, which offers a spa and bar/lounge in a beautiful location about 1 mile from Maho Beach.
How can I save money on a Simpson Bay vacation package?
When you bundle, you can save up to 30%*. To save money on a Simpson Bay package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
How much does a Simpson Bay vacation package cost?
A Simpson Bay vacation package typically costs around $1,400 per adult for a week-long trip. Lower-priced options start around $850 per adult, while premium packages can reach up to $2,250.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Simpson Bay vacation package deals?
The cheapest Simpson Bay vacation package deals can be as low as around $750 per adult for weekend trips. Separately, September and October typically have the lowest average monthly prices, around $1,070 to $1,130 per adult, typically for a 4-day trip. Bundling flights and hotel together also typically saves money on a week-long trip — nearly all Simpson Bay vacation package deals include some savings versus booking separately, typically around $165 per adult. Longer, two-week trips can save even more, often around $230 per adult. Many hotels in Simpson Bay offer free breakfast, which can help stretch your budget further. Browse cheap vacation packages in Simpson Bay on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Simpson Bay?
The best time to go for a Simpson Bay vacation package, based on peak booking trends, is typically from June to August. These months are the most popular for travelers visiting the area.For those seeking a more affordable Simpson Bay vacation, they can often find lower package prices from September to November. While these months might be quieter, they can be a good option for budget-conscious travelers.
What's included in a Simpson Bay vacation package?
A Simpson Bay vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Given Simpson Bay's focus on beaches, many hotels offer direct beach access, and most package hotels provide ocean views. Most resorts also offer airport shuttle service to and from Philipsburg (SXM-Princess Juliana Intl.) and over half include free breakfast, giving you a relaxed start to each day without extra planning.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Simpson Bay?
Families can find a great Simpson Bay vacation package with a stay at The Villas at Simpson Bay Resort, a 4-star property rated 8.5 out of 10 by travelers. This resort offers family rooms, an outdoor pool, and a playground, with travelers frequently praising the amazing rooms and fantastic location.For couples seeking a romantic escape, Mary's Boon Beach Resort & Spa, rated 8 out of 10 by travelers, provides a spa and bar/lounge in a beautiful setting about 1 mile from Maho Beach. Guests often highlight the super comfortable rooms and praise the staff.Travelers looking for a luxury Simpson Bay vacation package might consider The Morgan Resort Spa Village, a 4-star hotel rated 8.1 out of 10 by travelers. This resort features a spa and outdoor pool, with guests often noting the fantastic pool and great views from the rooms.For those seeking the best value, Baker's Suites, a 3.5-star hotel rated 8.7 out of 10 by travelers, is a strong choice. It offers amenities like free WiFi and kitchen facilities, and travelers frequently mention the fantastic staff and free breakfast.
Is Simpson Bay better suited for a beach vacation or a cultural trip?
Simpson Bay is primarily a beach destination, making it ideal for a relaxing Simpson Bay vacation focused on sun and sand. Most package hotels offer ocean views, and the area is home to numerous popular beaches like Maho Beach, known for plane spotting, and the namesake Simpson Bay Beach, about 2 miles from the center.Cultural attractions are part of the broader appeal of Sint Maarten.
Is Simpson Bay a good choice for a family vacation package?
Simpson Bay is a strong choice for family vacation packages, with some of the bookings being family trips. Many resorts cater to families with amenities like family rooms, outdoor pools, and playgrounds.For example, the 4-star Simpson Bay Resort, Marina & Spa, rated 8.1 out of 10 by travelers, offers family rooms, an outdoor pool, a playground, and a game room, with travelers praising the rooms and the great food, and with staff always smiling.Families can also enjoy the area's natural attractions, such as Maho Beach, about 3 miles from central Simpson Bay, or the more tranquil Simpson Bay Beach, about 2 miles from the center.
What's included in a Simpson Bay beach vacation package?
Simpson Bay beach vacation packages combine flights with a hotel stay, often providing direct access to the island's beautiful coastline. Hotels like the 4-star Simpson Bay Resort, Marina & Spa, rated 8.1 out of 10, offer amenities such as an outdoor pool, game room, and kitchen facilities, and travelers often highlight its convenient location and delicious breakfast. For a stay closer to the sand, Mary's Boon Beach Resort & Spa, rated 8 out of 10 and about 1 mile from Maho Beach, features an outdoor pool and spa, with travelers praising its super comfortable rooms and great overall experience. The 4-star The Morgan Resort Spa Village, rated 8.1 out of 10, is also a strong option, located about a 5-minute walk from Maho Beach and offering an outdoor pool and spa. Specific inclusions like meals, drinks, and activities depend on the hotel and rate you choose for your Simpson Bay vacation package.
Which Simpson Bay vacation packages include an ocean view?
Most Simpson Bay vacation package hotels offer rooms with ocean views, allowing you to enjoy the coastal scenery. The 4-star The Villas at Simpson Bay Resort, rated 8.5 out of 10, is a popular choice about 2 miles from Maho Beach, where travelers often highlight its amazing rooms and great food. Another excellent option is the 4-star The Morgan Resort Spa Village, rated 8.1 out of 10 and located about a 5-minute walk from Maho Beach, where travelers frequently mention the great views from the rooms and fantastic pool. Keep in mind that specific room types and rates determine whether an ocean view is included in your Simpson Bay vacation package.
What is the best time to book a Simpson Bay vacation package?
Book your Simpson Bay vacation package around 7 weeks in advance. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 4 and 12 weeks out.From June to August are the most popular months for Simpson Bay packages, so booking earlier is advisable if you're traveling during these times.
What are the top things to do in Simpson Bay?
A Simpson Bay vacation can combine beach relaxation with exploring the island's vibrant coastline:Browse and book things to do in Simpson Bay on Expedia.
How many days do you need for a Simpson Bay vacation?
Most Simpson Bay vacation packages typically last around 5 days. This duration allows ample time to enjoy the beautiful beaches like Maho Beach and Simpson Bay Beach, explore local dining, and relax by the pool.While some travelers opt for weekend trips, most choose week-long trips to fully experience the island. Some also extend their stay to around two weeks, which provides more opportunity for day trips to places like Orient Bay Beach and other island attractions.
Is Simpson Bay a good destination for a weekend vacation?
Simpson Bay can be a good choice for a weekend vacation package, especially if you're looking for a quick beach getaway. Some travelers choose weekend trips, allowing enough time to enjoy the immediate area's highlights like Maho Beach or the conveniently located Flamingo Beach, which is about a 5-minute walk from central Simpson Bay.While most travelers opt for week-long trips to explore more of the island, a focused weekend trip still offers a refreshing escape to the beaches of Simpson Bay.
Do you need to rent a car in Simpson Bay, or is public transport enough?
For a Simpson Bay vacation package, a rental car can offer flexibility for exploring the island, but it's not always essential, especially for a Simpson Bay beach vacation package focused on resort stays. Many hotels are conveniently located near Philipsburg (SXM-Princess Juliana Intl.) Airport, with some properties like The Morgan Resort Spa Village being about a 10-minute walk away, and The Villas at Simpson Bay Resort about 1 mile away.Since Simpson Bay is a beach destination outside a major city, many resorts provide on-site dining and activities, reducing the need to travel daily. However, if you plan to visit multiple beaches or explore different parts of Sint Maarten, a rental car will provide the most freedom.
Are Simpson Bay vacation package hotels conveniently located?
Simpson Bay vacation package hotels offer a range of convenient locations, from properties within walking distance of the central area to those a short drive away.For instance, Azure Hotel and Art Studio is about a 5-minute walk from central Simpson Bay, while Baker's Suites is about a 10-minute walk. If you prefer a slightly more secluded spot, The Morgan Resort Spa Village is about 2 miles from central Simpson Bay. This variety means you can choose a location that best suits your preference for proximity to local shops and restaurants or a quieter resort experience.
Can I change or cancel my Simpson Bay vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Simpson Bay vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Simpson Bay vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Simpson Bay vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Simpson Bay?
To find last-minute vacation packages to Simpson Bay, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Simpson Bay vacation packages?
Free cancellation on a Simpson Bay vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Simpson Bay vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Simpson Bay getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Simpson Bay vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.