
Simpson Bay Holidays from NZ$4,852
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Simpson Bay Holiday Deals
Price found within the past 48 hours. Click for updated prices.



La Playa Orient Bay
per person
21 Jun - 27 Jun
found 23 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9.4/10 Exceptional! (482 reviews)
The hotel was the same as the pictures on their website. The room we had on the third floor was excellent with a nice size refrigerator and freezer which we used only to store some wine, water and I made some ice just because there was an ice tray. The hotel had a very convenient large ice machine. The staff were very friendly and helpful for the most part ,we had some miscommunication issues with the staff replenishing the coffee in the room but they made up for it by giving us some extra. It was no big deal. Only other issue was that when we went to lunch the first few days at the very convenient beach side restaurant the staff kept asking us if we had reservations even though the restaurant was never fully occupied. We then said we would like a reservation every day for lunch and the issue ended. The restaurant had many tables available every day so I’m not sure why they made such a requirement. The breakfast was a nice meal with a great view. Very relaxing way to start the day. There are many restaurants (8 or 9) for dinner a short walk from the hotel as well as a two small grocery stores which also sell wine and spirits, a good pizzeria ,ice cream shop, bakery and deli. Everything you would need plus a beautiful beach.
Reviewed on 29 Apr. 2025

Esmeralda Resort
per person
21 Jun - 27 Jun
found 23 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
8.6/10 Excellent! (446 reviews)
Location is amazing! Staff is too! Swimming pool right outside the patio door, mini kitchen worked great. L’Astrolabe breakfast was perfect and dinners were too! Fridays and Mondays are a do not miss. A few quick minutes to the beach where your chair awaits, with staff to help you there! The beach restaurant’s food is also amazing! If you do not rent a car, it is easy to get a taxi. I used the same person the whole time. He was great. This property is lovely and I would definitely come back! There’s bird watching, the surf is perfect, food, entertainment for my style, bar, and no clocks. It is lovely.
Reviewed on 26 Apr. 2025

Holland House Beach Hotel
per person
21 Jun - 27 Jun
found 23 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9/10 Wonderful! (1,002 reviews)
Beautiful and clean! Staff always about to assist in anything needed. Reuben, Kelly and Kenisha at the beach bar were so great
Reviewed on 30 Apr. 2025
Simpson Bay Holiday
Our pick of the best Simpson Bay Hotel Deals

Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
The price is NZ$243 per night from 17 May to 18 May
NZ$243
includes taxes & fees
17 May - 18 May
8.8/10 Excellent! (1,082 reviews)
"Property was very nice and well maintained. My room was very clean and spacious. There were many dining options nearby."
Reviewed on 30 Apr. 2025

The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is NZ$653 per night from 4 May to 5 May
NZ$653
includes taxes & fees
4 May - 5 May
8.8/10 Excellent! (1,651 reviews)
"The staff was Amazing! Super friendly and Helpful! I needed a last min trip to drug store in the pouring rain and they were able to take me on one of their airport drop offs so I wouldnt get soaked!!! Great stay Thanks again!"
Reviewed on 28 Apr. 2025

Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is NZ$230 per night from 11 May to 12 May
NZ$230
includes taxes & fees
11 May - 12 May
9/10 Wonderful! (1,001 reviews)
"Wonderful stay!"
Reviewed on 29 Apr. 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.
Discover the most popular places to visit in Simpson Bay

Kim Sha Beach
Why not spend a care-free afternoon at Kim Sha Beach during your travels in Simpson Bay? Visit the shops and lively bars in this romantic area.

Hollywood Casino
Soak up some Hollywood glamour at this relaxed and intimate casino, complete with piano bar and buffet.
Lay Bay Beach
Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?
What to do in Simpson Bay

Ultimate Prickly Pear and Anguilla Experience
NZ$251
per adult
84% of travellers recommend

Edge Ferry Tickets to St. Barts
NZ$168
per adult
84% of travellers recommend

Tango Sunset Cruise with Caribbean Dinner & Open Bar
NZ$143
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.