Sint Maarten Luxury Vacations
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Top Luxury vacation packages in Sint Maarten
Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key
Price was $621, price is now $491 per person
$491
per person
Jan 29 - Jan 31
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
9/10 Wonderful! (1,339 reviews)
Enjoyed it very much! Beautiful room and great staff!
Reviewed on Nov 27, 2025
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $1,657, price is now $677 per person
$677
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Beach was amazing, our room was on the first floor facing the parking.. therfore did not really like that. Tried to change but they said no other availability.
Restaurants are close by. Roads around the complex need some major repairs.
We rented a car which made it easier to get around.
Rooms were clean, staff very friendly.
Would definately return but in a different room.
Reviewed on Nov 29, 2025
Holland House Beach Hotel
Downtown Philipsburg
Save 100% on your flight
Price was $1,112, price is now $683 per person
$683
per person
Feb 1 - Feb 4
found 10 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
This was our 2nd stay at the holland in a 3 month period. We love the entire island, beautiful beaches all around. You have amazing and delicious restaurants all around at walking distance from the hotel. 100% recommend the restaurant at the property. A lot of shopping stores up and down the entire area. Everything does close early here (5pm, each place has its own time) which to us was no issue at all. There are a few restaurants near or close by that do close later in the night. We did rent a car to explore the island and were able to go have late dinners at other places outside of downtown philipsburg. I would strongly recommend getting a rental. Walking on to the property you see the beautiful view of the beach, the balcony view is breath taking. You have beach access with beach chairs, umbrella and towels. Our second stay the bed was super comfortable. The rooms are amazing with great space, very accommodating, clean and stocked with the toiletry needed. Truly a great place to stay, and for a fact is due to all the hard working staff. The staff is AMAZING and they make your stay very welcoming…I can go on and on about how great the entire staff is. The holland will be our place to stay anytime we come back.
Reviewed on Nov 24, 2025
Divi Little Bay Beach Resort
Price was $1,611, price is now $1,142 per person
$1,142
per person
Jan 4 - Jan 7
found 2 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
I reached out to management several times regarding the issues with my stay and have yet to hear back from anyone.
Reviewed on Nov 27, 2025
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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 $1,094, price is now $932 per person
$932
per person
Jan 29 - Jan 31
found 2 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
8.6/10 Excellent! (1,001 reviews)
The overall hotel was great, the food and staff were wonderful! I wish they had more adult only entertainment. The beach and ocean being feet away and watching the planes land and take off was really special though! I would definitely recommend staying here unless you are highly allergic to cats as there were many around the property but if you can get away with just some allergy meds, the view and sunsets are incredibly worth it!
Reviewed on Nov 25, 2025
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View all trips3 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 $1,657, price is now $677 per person
$677
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Beach was amazing, our room was on the first floor facing the parking.. therfore did not really like that. Tried to change but they said no other availability.
Restaurants are close by. Roads around the complex need some major repairs.
We rented a car which made it easier to get around.
Rooms were clean, staff very friendly.
Would definately return but in a different room.
Reviewed on Nov 29, 2025
The Villas at Simpson Bay Resort
Save 100% on your flight
Price was $1,921, price is now $933 per person
$933
per person
Jan 29 - Feb 1
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,309 reviews)
There was a smell of sewage every night
Reviewed on Nov 27, 2025
Divi Little Bay Beach Resort
Save 100% on your flight
Price was $1,786, price is now $1,202 per person
$1,202
per person
Jan 29 - Feb 1
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
I reached out to management several times regarding the issues with my stay and have yet to hear back from anyone.
Reviewed on Nov 27, 2025
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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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
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Price was $1,228, price is now $763 per person
$763
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
St. John's (ANU) to Philipsburg (SXM)
9.2/10 Wonderful! (973 reviews)
This place puts the z in ZEN great value for a great price. You will have to be ready to walk its very mountainous so walking to b a r and few food choices is a little walk but besides that allllll great vibes
Reviewed on Nov 28, 2025
Simpson Bay Resort, Marina & Spa
Pelican Key
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Price was $2,451, price is now $1,136 per person
$1,136
per person
Jan 29 - Feb 2
found 23 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Beach was amazing, our room was on the first floor facing the parking.. therfore did not really like that. Tried to change but they said no other availability.
Restaurants are close by. Roads around the complex need some major repairs.
We rented a car which made it easier to get around.
Rooms were clean, staff very friendly.
Would definately return but in a different room.
Reviewed on Nov 29, 2025
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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 $491. 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. Lowlands
$573 nightly
The price is $598 total per night from Dec 3 to Dec 4
$598 total
Dec 3 - Dec 4
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, ...
8.6/10 Excellent! (1,006 reviews)
The overall hotel was great, the food and staff were wonderful! I wish they had more adult only entertainment. The beach and ocean being feet away and watching the planes land and take off was really special though! I would definitely recommend staying here unless you are highly allergic to cats ...
Reviewed on Nov 25, 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 Oyster Pond
$145 nightly
The price is $151 total per night from Nov 30 to Dec 1
$151 total
Nov 30 - Dec 1
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! (976 reviews)
The room was spacious, clean and had adequate storage. The kitchenette was properly outfitted and they gave us a few complimentary drinks, The place was very quiet and private.
Reviewed on Nov 26, 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.
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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.
