Search Deals onPhilipsburg Vacation Packages
Philipsburg Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort
Price was $1,434, price is now $1,051 per person
$1,051
per person
Dec 22 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Philipsburg (SXM)
Book a stay at this spa resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Port of St. Maarten and Grand Case Beach are located nearby.
The Villas at Simpson Bay Resort
Save 100% on your flight
Price was $1,929, price is now $1,103 per person
$1,103
per person
Dec 16 - Dec 20
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Loved it all complimentary bottle of Chilean wine. We had an ocean/pool view one bedroom villa and just loved it. Absolutely loved the staff especially Monique who had amazing dinner recommendations for us at her fingertips. Ask for her! 10/10
Reviewed on Oct 9, 2026
Princess Heights Luxury Boutique Condo Hotel
Save 100% on your flight
Price was $1,953, price is now $1,203 per person
$1,203
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
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 clean rooms in our reviews. Popular attractions Port of St. Maarten and Grand Case Beach are located nearby.
Divi Little Bay Beach Resort
Save 100% on your flight
Price was $2,690, price is now $1,829 per person
$1,829
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Port of St. Maarten are located nearby.
We had an amazing experience at Divi Resorts! The resort was beautiful, clean, and well-maintained, with breathtaking views and a relaxing atmosphere. The staff was friendly, welcoming, and always willing to help. The amenities, food, and overall experience made our stay truly enjoyable. It was the perfect getaway to relax, unwind, and create unforgettable memories. We would definitely recommend Divi Resorts to anyone looking for a wonderful vacation experience. We look forward to returning!
Reviewed on Oct 8, 2026
Panorama Residences at Monte Vista
Save 100% on your flight
Price was $2,103, price is now $1,436 per person
$1,436
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
Book a stay at this luxury aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Maho Beach and Port of St. Maarten are located nearby.
Amazing stay
Reviewed on Oct 6, 2026
Oceans at Divi Little Bay
Save 100% on your flight
Price was $2,631, price is now $1,833 per person
$1,833
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
Stay at this hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Port of St. Maarten are located nearby.
Hands down 1 of my favorite resorts!! The staffs was AMAZING!!! Can’t wait to visit again soon
Reviewed on Oct 9, 2026
The Atrium Beach Resort and Spa, an Ascend Collection Resort
Price was $1,661, price is now $1,202 per person
$1,202
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The Morgan Resort Spa Village
Price was $2,377, price is now $1,737 per person
$1,737
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Philipsburg (SXM)
Book a stay at this spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Outstanding
Reviewed on Oct 7, 2026
Philipsburg Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Philipsburg Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Oct 26 - Wed, Oct 28
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$299 Roundtrip, found 20 hours ago
$299
Roundtrip
found 20 hours ago
Mon, Nov 16 - Fri, Dec 4
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Mon, Nov 2 - Fri, Nov 6
YYZ
Pearson Intl.
SXM
Princess Juliana Intl.
$326 Roundtrip, found 4 days ago
$326
Roundtrip
found 4 days ago
Sat, Jan 16 - Wed, Feb 17
YUL
Pierre Elliott Trudeau Intl.
SXM
Princess Juliana Intl.
$362 Roundtrip, found 1 day ago
$362
Roundtrip
found 1 day ago
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