Simpson Bay Holidays

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Top Flight + Hotel Deals in Simpson Bay

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
29 Aug - 31 Aug
found 13 hours ago
Return direct flight included
Orlando (MCO) to Philipsburg (SXM)
8.8/10 Excellent! (1,144 reviews)
We liked the beach and reef for snorkeling.

Reviewed on 27 Jun 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
10 Aug - 17 Aug
found 1 day ago
Return flight included
Toronto (YYZ) to Philipsburg (SXM)
8.6/10 Excellent! (883 reviews)
Excellent property. Will come back.

Reviewed on 20 Jun 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
per person
10 Aug - 17 Aug
found 1 day ago
Return flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
Great customer service from everyone we came in contact with.

Reviewed on 25 Jun 2025

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key
per person
10 Aug - 17 Aug
found 1 day ago
Return flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,045 reviews)
La amabilidad de los empleados, buen desayuno, la habitación excelente

Reviewed on 27 Jun 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
29 Aug - 31 Aug
found 13 hours ago
Return direct flight included
Orlando (MCO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,182 reviews)
Staff was exceptionally sweet and took care of our needs and concerns. I would keep in mind though a lot of these amenities are labelled "on property" but they are off the resort, a very short walk. But if traveling solo it is good to note. Also, there was a very big incident where a roach was in our room/balcony. The staff worked immediately to change our room and it was not a problem again, but if you are someone like me, it def gave a type of vibe to the trip and ruined any relaxation on stressing if itll happen again.

Reviewed on 25 Jun 2025

Simpson Bay Beach Holiday

There's nothing like a Simpson Bay holiday 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 centre on your trip to Simpson Bay, find a hotel around Simpson Bay Beach (just 2 kilometres away). If you're planning to stay for a while, take a peek at our Simpson Bay holiday 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 holiday? See what's available — there's nothing like staying at just minutes from the water.
  • If your idea of an amazing beach holiday involves staying in one of our villas, Cocovaa or The Morgan Resort & Spa will suit you perfectly.

Top hotels in Simpson Bay

The Morgan Resort Spa Village
The Morgan Resort Spa Village
4 out of 5
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,716 reviews)
"Rooms were clean, staff was friendly"

Reviewed on 23 Jun 2025

Get rates
The Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa
Simpson Bay Resort, Marina & Spa
4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is €101 per night from 7 Jul to 8 Jul
€101
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (1,162 reviews)
"Great location, very clean, friendly people"

Reviewed on 23 Jun 2025

Simpson Bay Resort, Marina & Spa
Hilton Vacation Club Flamingo Beach St. Maarten
Hilton Vacation Club Flamingo Beach St. Maarten
4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is €146 per night from 8 Jul to 9 Jul
€146
8 Jul - 9 Jul
includes taxes & fees
9/10 Wonderful! (1,059 reviews)
"It was very relaxing and cozy. My wife and I didn’t want to leave."

Reviewed on 24 Jun 2025

Hilton Vacation Club Flamingo Beach St. Maarten
See all 434 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.

Frequently asked questions

How much does a Simpson Bay holiday package cost?
You'll find cheap prices from €564 on Expedia for your Simpson Bay getaway. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Simpson Bay costs.
What are the cheapest months to go to Simpson Bay?
September, October and November are the best times to look for cheap Simpson Bay holiday packages. Travelling in quieter periods means you can generally find reduced prices on flights and accommodation.
How many days is enough for Simpson Bay?
We recommend booking a Simpson Bay holiday for at least 4 days. This will allow you plenty of time to visit top sights such as Kim Sha Beach and Lay Bay Beach, and also explore neighbourhoods like Pelican Key and Upper Prince's Quarter. You could even fit in a day trip outside of Simpson Bay.
Is it worth booking a holiday package to Simpson Bay?
Well known for its coastal beaches and home to leading attractions like Simpson Bay Beach, a Simpson Bay holiday is sure to impress. Another top sight worth exploring? Don't miss Flamingo Beach.
How to find the best Simpson Bay package deals?
Start your search for a Simpson Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Simpson Bay package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Simpson Bay adventure off to a flying start.
Is it cheaper to book a Simpson Bay holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging stays and flights individually. Better still, you can customise your Simpson Bay escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Simpson Bay?
If you're considering a spontaneous Simpson Bay trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Simpson Bay?

  1. Choose your travel dates: What you want to do in Simpson Bay and your favourite season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will likely be the largest expense during your trip to Simpson Bay.
  3. Decide how long to go away for: Now that you're up to speed on Simpson Bay, you can work out the ideal length of your break. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, lock in the perfect Simpson Bay holiday package for you.

Popular places to visit

Hollywood Casino featuring a casino and interior views

Hollywood Casino

Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.

Hollywood Casino

Lay Bay Beach

Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?

Lay Bay Beach

What to do in Simpson Bay

Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

€130
per adult
80% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
Pinel Island!!

Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten

€121
per adult
100% of travellers recommend
Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

€87
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
See all activities in Simpson Bay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.