Romantic Vacations in Sint Maarten 2026

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Flight and Romantic hotel deals in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

Oyster Bay Beach Resort

Oyster Pond

CA $1,067

per person

Oct 16 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

8.8/10 Excellent! (999 reviews)

The room was clean, the staff was friendly they upgraded the room. Also did a spa day it was a lovely experience.

Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort

Pelican Key

CA $1,350

per person

Oct 16 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,484 reviews)

We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.

Reviewed on Aug 16, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,103

per person

Oct 16 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

9/10 Wonderful! (1,922 reviews)

The staff were amazing, food was great, beach was clean and very easy to access. Our only small issues were that it was not really handicapped friendly, and parking was tight. We had a big van that we rented to hold my dad motorized wheel chair and we had to take up 2 spots each time we parked or we wouldn’t be able to get in the car if someone parked next to us. The curbs did not have handicapped access to get on and off with the motorized wheelchair. It was amazing other wise and we would return in the future.

Reviewed on Aug 16, 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $3,023

per person

Oct 16 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

8.8/10 Excellent! (1,003 reviews)

Holland House Beach Hotel

Downtown Philipsburg

CA $1,433

per person

Oct 16 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,006 reviews)

Great stay. Good location. Beautiful beach. Breakfast was wonderful.

Reviewed on Aug 14, 2026

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5* Romantic holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $3,023

per person

Oct 16 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) 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 Romantic holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

Oyster Bay Beach Resort

Oyster Pond

CA $723

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

8.8/10 Excellent! (999 reviews)

The room was clean, the staff was friendly they upgraded the room. Also did a spa day it was a lovely experience.

Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort

Pelican Key

CA $907

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,484 reviews)

We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.

Reviewed on Aug 16, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $762

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9/10 Wonderful! (1,922 reviews)

Reviewed on Aug 16, 2026

Don't see what you're looking for?

See all available trips from Columbus to Sint Maarten

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4 Night Romantic holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $853

per person

Oct 29 - Nov 2

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9/10 Wonderful! (1,922 reviews)

Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort

Pelican Key

CA $1,061

per person

Oct 22 - Oct 26

just found

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,484 reviews)

We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.

Reviewed on Aug 16, 2026

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $934

per person

Oct 22 - Oct 26

just found

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,003 reviews)

The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.

Reviewed on Aug 13, 2026

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What are some of the benefits of booking a romantic Sint Maarten vacation?

When booking a romantic Sint Maarten vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Caribbean.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Sint Maarten destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Sint Maarten?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $723 and can enjoy savings of up to 32 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Sint Maarten?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Sint Maarten certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Sint Maarten.

Can I book a romantic Sint Maarten vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Sint Maarten search.

Can I book a romantic trip to Sint Maarten that is fully refundable?

Several romantic Sint Maarten vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.

Romantic Hotels in Sint Maarten

Sonesta Ocean Point All Inclusive, Adults Only Resort

1A Rhine Rd. Lowlands

4 min walk from Maho Beach

CA $873

CA $1,056 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 Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

4 min walk from Maho Beach

CA $551

CA $634 total

Sep 8 - Sep 9

includes taxes & fees

Book a stay at this beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...

Great Bay Beach Resort, Casino & Spa

Little Bay Rd 19 Philipsburg

8 min drive from Maho Beach

Book a stay at this luxury property in Philipsburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maho Beach and Great Bay Beach are ...

7.4/10 Good! (486 reviews)

Hotel is nice for a smaller hotel.

"Food was great! A majority of the staff was great! Tried the rooms with Bali beds out front and that was a waste of money. No view and filled with ants. Get a higher room with an ocean view. The beach was useless as it is steep and ground seashells for sand. That said, you cannot beat the view of ..."

Reviewed on Jan 24, 2018

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See all 1,662 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.