Sint Maarten Luxury Vacations

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Flight and Luxury hotel deals in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,074
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,333
per person
Oct 11 - Oct 18
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
I would stay there again

Reviewed on Aug 11, 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $2,336
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

CA $2,585
per person
Oct 11 - Oct 18
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8/10 Very good! (3,112 reviews)
Amazing

Reviewed on Aug 11, 2026

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

Oyster Pond
CA $1,634
per person
Oct 11 - Oct 18
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (119 reviews)
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.

Reviewed on Jul 19, 2026

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5* Luxury holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $2,336
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Sint Maarten
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3 Night Luxury holidays in Sint Maarten

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

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $754
per person
Oct 15 - Oct 18
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
I would stay there again

Reviewed on Aug 11, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $885
per person
Oct 15 - Oct 18
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
CA $871
per person
Oct 15 - Oct 18
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,006 reviews)
Very nice hotel, centrally located. The staff were very nice. My only complaint, the bathroom was very nice looking, but not functional.

Reviewed on Aug 10, 2026

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4 Night Luxury holidays in Sint Maarten

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

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $822
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
I would stay there again

Reviewed on Aug 11, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,155
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $2,449
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
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Plan the perfect luxury Sint Maarten vacation with Expedia

What are some benefits when booking luxury Sint Maarten vacations?

When you book a luxury Sint Maarten vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Sint Maarten?

If you're looking for something luxurious in Sint Maarten, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $754, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 57. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Sint Maarten. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Sint Maarten?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Sint Maarten.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Sint Maarten. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Sint Maarten?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Sint Maarten or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Sint Maarten. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Sint Maarten

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

1A Rhine Rd. Lowlands
  • 4 min walk from Maho Beach
CA $877
CA $1,061 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this luxury property in Lowlands. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Sonesta Ocean Point All Inclusive, Adults Only Resort
Villa Bianca

Villa Bianca

Ruby Drive, Pelican Key Simpson Bay
  • 4 min drive from Maho Beach
Book a stay at this luxury villa in Simpson Bay. Enjoy free WiFi, free parking, and private pools. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Villa Bianca
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond Road No 156 Oyster Pond
  • 12 min drive from Maho Beach
CA $207
CA $248 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,010 reviews)
"This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again ."

Reviewed on Aug 8, 2026

Princess Heights Luxury Boutique Condo Hotel
See all 1,667 properties in Sint Maarten
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.

Things to do

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $114
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Colorful Species Of Birds

Colorful Species Of Birds

CA $69
per adult
94% of travellers recommend
Colorful Species Of Birds
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $190
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Sint Maarten

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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.