Sint Maarten Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 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
Top Luxury vacation packages in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
Price was $654, price is now $457 per person
$457
per person
Sep 27 - Sep 29
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
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
Divi Little Bay Beach Resort
Price was $983, price is now $780 per person
$780
per person
Sep 22 - Sep 25
found 12 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
8.4/10 Very Good! (1,003 reviews)
All inclusive did not include Coffee Shop or certain Vodka like Tito’s!
Reviewed on Aug 19, 2025
Holland House Beach Hotel
Downtown Philipsburg
Price was $857, price is now $680 per person
$680
per person
Sep 22 - Sep 25
found 12 hours ago
Roundtrip flight included
New York (JFK) 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
Hilton Vacation Club Royal Palm St. Maarten
Price was $720, price is now $591 per person
$591
per person
Sep 22 - Sep 25
found 12 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
The property had laundry facilities. It is located near restaurants and convenience store. Plenty of parking. The pool and the beach is directly across from the lobby. The furnitures are new. The bed is very comfortable. The view from the living room and balcony is very nice.
Reviewed on Aug 22, 2025
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips5* Luxury vacations in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort
Price was $1,241, price is now $1,198 per person
$1,198
per person
Sep 22 - Sep 25
found 15 hours ago
Roundtrip non-stop flight included
New York (LGA) to Philipsburg (SXM)
8.6/10 Excellent! (1,005 reviews)
The location of the property was ideal. Close to Maho beach. The property was well kept, however the food was a bit too monotonous. Pretty the same thing rotated for the different nights. Some staff were helpful and pleasant but most of them were just "there". Some of them expressed their displeasure of working there.
Reviewed on Aug 22, 2025
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips3 Night Luxury vacations in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
Price was $1,213, price is now $849 per person
$849
per person
Oct 23 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
Holland House Beach Hotel
Downtown Philipsburg
Price was $1,189, price is now $882 per person
$882
per person
Oct 23 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all trips4 Night Luxury vacations in Sint Maarten
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
Price was $1,350, price is now $869 per person
$869
per person
Oct 23 - Oct 27
found 6 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Holland House Beach Hotel
Downtown Philipsburg
Price was $1,324, price is now $915 per person
$915
per person
Oct 23 - Oct 27
found 6 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
View all tripsAll you need to know about luxury vacations in Sint Maarten
What can I expect from a luxury Sint Maarten vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Sint Maarten vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views.
How can I find all-inclusive luxury vacation packages in Sint Maarten?
By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger.
Can I book a cheap Sint Maarten luxury vacation?
Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $457. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in Sint Maarten?
Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi.
Can I book a package in Sint Maarten with a luxury vacation home?
A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.
How can I find the best luxury vacation deals in Sint Maarten?
Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.
Can I book a luxury holiday in Sint Maarten with free cancellation and/or flexible dates?
Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan.
Why should I book my luxury trip to Sint Maarten with Expedia?
A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.
Top Luxury Sint Maarten Hotels
Sonesta Ocean Point All Inclusive, Adults Only Resort
1A Rhine Rd., Maho Bay, Lowlands
$533 nightly
The price is $556 total per night from Aug 30 to Aug 31
$556 total
Aug 30 - Aug 31
Total with taxes and fees
Sonesta Ocean Point All Inclusive, Adults Only Resort is a Lowlands luxury 5-star all-inclusive property where you can pamper yourself with Champagne service, ...
8.4/10 Very Good! (1,006 reviews)
"The overall resort and staff was wonderful. My husband and I enjoyed our stay. The only reason I did not give 5 stars on everything was because when I turned the AC to fan mode the ceiling started to leak, they did send maintenance to fix and clean it up. It happened the next day and no one ever ..."
Reviewed on Aug 20, 2025
Villa Bianca
Ruby Drive, Pelican Key, Simpson Bay
Enjoy a lavish stay at this villa, where you'll find private pools and premium bedding. The outdoor pool and terrace are just some of the popular amenities at ...
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond Road No 156, Dawn Beach, Oyster Pond
$149 nightly
The price is $156 total per night from Aug 24 to Aug 25
$156 total
Aug 24 - Aug 25
Total with taxes and fees
Enjoy a posh stay at Princess Heights Luxury Boutique Condo Hotel, where you'll find jetted bathtubs and premium bedding. The outdoor pool, 24-hour fitness center, ...
9.2/10 Wonderful! (958 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 ..."
Reviewed on Aug 15, 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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.