Simpson Bay Vacations from $580
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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.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $932, price is now $580 per person
$580
per person
Oct 28 - Nov 1
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
Love this place it’s like my second home
Reviewed on Aug 21, 2025
The Villas at Simpson Bay Resort
Save 100% on your flight
Price was $1,563, price is now $900 per person
$900
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Beautiful and clean resort with a stunning views. The bed was comfortable, and it was short walk to restaurants. However, there are about three on-site restaurants, and they are quite expensive.
Reviewed on Aug 22, 2025
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $1,364, price is now $790 per person
$790
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
This property was very nice and astonishing. The area was quiet and lovely place to have a vacation at. The beds were so comfortable after a day of activities and excursions. The place is very peaceful and beautiful. The staff were amazing as well. The views were amazing. I would definitely recommend.
Reviewed on Aug 15, 2025
Holland House Beach Hotel
Downtown Philipsburg
Save 100% on your flight
Price was $1,628, price is now $985 per person
$985
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
My husband and I spent our anniversary at Holland House and absolutely loved our stay. The hotel has a charming outdoor atmosphere, and our room was clean with a beautiful ocean view. The location is perfect—close to everything, yet peaceful. The staff were welcoming and incredibly pleasant, which made our stay even more special.
Although we didn’t have breakfast at the hotel, we did enjoy dinner one evening, which was delicious and made even better by the lovely live music. We truly had a wonderful experience and would love to stay here again.
Reviewed on Aug 18, 2025
Esmeralda Resort
Save 100% on your flight
Price was $1,242, price is now $785 per person
$785
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.6/10 Excellent! (464 reviews)
Nice having semi-private pool. All of the staff very friendly and helpful. Including at L'Astrolabe for breakfast and dinner.
Reviewed on Jun 13, 2025
Don't see what you're looking for?
See all available trips from Columbus to Simpson Bay
View all tripsDiscover the most popular places to visit in Simpson Bay
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
Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.
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.
What to do in Simpson Bay
Ultimate Prickly Pear and Anguilla Experience
$149
per adult
84% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
$85
per adult
94% of travellers recommend
Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten
$139
per adult
100% of travellers recommend
Simpson Bay Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $101 total per night from Aug 31 to Sep 1
$101 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (1,304 reviews)
Wonderful Stay
"We have stayed here many times over the years and really enjoy it. Great location, friendly staff (for the most part) and nice beach and pools. We find the Simpson Bay Resort a good value when visiting St Maarten."
Reviewed on Aug 21, 2025
The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $250 total per night from Aug 25 to Aug 26
$250 total
Aug 25 - Aug 26
Total with taxes and fees
8.8/10 Excellent! (1,813 reviews)
"All the staff were awesome, we loved the pool and the swim up bar. Food was very good. Whenever we had a question or concerns, there was always a staff person with an answer or a solution. Great stay !"
Reviewed on Aug 20, 2025
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $152 total per night from Aug 26 to Aug 27
$152 total
Aug 26 - Aug 27
Total with taxes and fees
9/10 Wonderful! (1,169 reviews)
"Staff were very helpful and friendly. Room was clean and well equipped."
Reviewed on Aug 20, 2025
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.
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.
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- Car rentals near Paradise Plaza
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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.