Sint Maarten Romantic Holidays

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    Packages with flights are ATOL protected

Top flight + Romantic hotel deals in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

Oyster Pond
£1,297
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
8.8/10 Excellent! (1,010 reviews)
Overall a great experience. Runs were very clean and plenty of AC. The pill was nice, just needs a little maintenance on tiles to be really nice. The staff was awesome-CeeJay, Chris and Nubi at the Veranda were very nice and fun to be around. The only downside was the whiff of sewer that was coming from somewhere in the area near the entrance of the property, but never smelled it from rims or anywhere else. We had a great time.

Reviewed on 6 Sept 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
£1,456
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Dinner on the beach was excellent view and music

Reviewed on 6 Sept 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
Save 100% on your flight
£1,341
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
Staff was helpful

Reviewed on 6 Sept 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
£2,134
per person
21 Oct - 25 Oct
found 1 day ago
Return direct flight included
Pensacola (PNS) to Philipsburg (SXM)
8.8/10 Excellent! (1,005 reviews)
Room was clean and spacious. Staff was friendly and gracious especially Smiley and Maddy. Staff was very helpful. Pools were relaxing edge pool needs a good cleaning and music

Reviewed on 5 Sept 2026

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
£1,432
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The View🏖️

Reviewed on 1 Sept 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

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
£2,134
per person
21 Oct - 25 Oct
found 1 day ago
Return direct flight included
Pensacola (PNS) to Philipsburg (SXM)
8.8/10 Excellent! (1,005 reviews)
Room was clean and spacious. Staff was friendly and gracious especially Smiley and Maddy. Staff was very helpful. Pools were relaxing edge pool needs a good cleaning and music

Reviewed on 5 Sept 2026

Don't see what you're looking for?
See all available trips from Pensacola to Sint Maarten
View all trips

4 Night Romantic holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
£752
per person
21 Oct - 25 Oct
found 1 day ago
Return direct flight included
Pensacola (PNS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
£802
per person
21 Oct - 25 Oct
found 1 day ago
Return direct flight included
Pensacola (PNS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Dinner on the beach was excellent view and music

Reviewed on 6 Sept 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
£2,134
per person
21 Oct - 25 Oct
found 1 day ago
Return direct flight included
Pensacola (PNS) to Philipsburg (SXM)
8.8/10 Excellent! (1,005 reviews)
Room was clean and spacious. Staff was friendly and gracious especially Smiley and Maddy. Staff was very helpful. Pools were relaxing edge pool needs a good cleaning and music

Reviewed on 5 Sept 2026

Don't see what you're looking for?
See all available trips from Pensacola to Sint Maarten
View all trips

How to find a romantic Sint Maarten holiday

How can I find the best Sint Maarten vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Sint Maarten. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Sint Maarten romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Sint Maarten that start from £752. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Sint Maarten romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Sint Maarten?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Sint Maarten?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Sint Maarten that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Sint Maarten with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Sint Maarten romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Sint Maarten Hotels

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
£601
per night
27 Sept - 28 Sept
Stay at this luxury resort in Lowlands. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,012 reviews)

Couples like: adults-only property, full-service spa, couples spa treatments, restaurant with ocean view

Travellers say...
"Room was clean and spacious. Staff was friendly and gracious especially Smiley and Maddy. Staff was very helpful. Pools were relaxing edge pool needs a good cleaning and music"

Reviewed on 5 Sept 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands
  • 4 min walk from Maho Beach
£313
per night
13 Sept - 14 Sept
Stay at this beach resort in Lowlands. Enjoy free Wi-Fi, 2 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
Sonesta Maho Beach All Inclusive Resort Casino & Spa
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

Little Bay Road Philipsburg
  • 8 min drive from Maho Beach
£150
per night
3 Oct - 4 Oct
Stay at this beach resort in Philipsburg. Enjoy free Wi-Fi, free parking and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in their ...
Divi Little Bay Beach Resort
See all 1,665 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

St Maarten Beach hopping tour

St Maarten Beach hopping tour (Oreint beach and Maho beach combo)

£44
per adult
St Maarten Beach hopping tour (Oreint beach and Maho beach combo)
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

£117
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

£56
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
See all activities in Sint Maarten

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Where to go when
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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. Flight-inclusive packages are ATOL protected.