Search Deals onSimpson Bay Vacation Packages
Simpson Bay Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Coral Beach Club Villas & Marina
Price was $1,224, price is now $907 per person
$907
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Book a stay at this spa resort in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Orient Bay and Pinel Island are located nearby.
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.
Reviewed on Jul 19, 2026
Princess Heights Luxury Boutique Condo Hotel
Save 100% on your flight
Price was $2,117, price is now $1,354 per person
$1,354
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 Pinel Island and Grand Case Beach are located nearby.
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
Sonesta Ocean Point All Inclusive, Adults Only Resort
Save 100% on your flight
Price was $3,695, price is now $2,546 per person
$2,546
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
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 our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Panorama Residences at Monte Vista
Price was $2,156, price is now $1,528 per person
$1,528
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 Harbour Point Village are located nearby.
The property was well maintained. The room was stunning and the views were spectacular! Ms Nicky referred me to a driver who was prompt and reliable. I would 100% recommend this property to anyone looking to vacay in St Maarten!!
Reviewed on Aug 27, 2026
Holland House Beach Hotel
Price was $1,972, price is now $1,407 per person
$1,407
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
Book a stay at this beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Maho Beach and Port of St. Maarten are located nearby.
Very exciting and fun. Great location, great staff!!
Reviewed on Aug 28, 2026
Oyster Bay Beach Resort
Price was $1,644, price is now $1,174 per person
$1,174
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 Orient Bay and Port of St. Maarten are located nearby.
The Forest
Price was $2,302, price is now $1,797 per person
$1,797
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
Book a stay at this family-friendly aparthotel in Anse Marcel. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Grand Case Beach and Orient Bay are located nearby.
What a wonderful stay!! The staff was exceptional and accommodating the entire trip. The rooms were clean and very beautiful, not to mention the landscaping and the ease of getting to and from. I will most certainly be back!! Thank you!!!
Reviewed on May 11, 2026
Sapphire Beach Club Resort
Price was $1,353, price is now $1,066 per person
$1,066
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
Book a stay at this beach resort in Lowlands. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Simpson Bay Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Simpson Bay 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 5 - Fri, Oct 9
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$295 Roundtrip, found 14 hours ago
$295
Roundtrip
found 14 hours ago
Sat, Oct 3 - Sat, Oct 10
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$322 Roundtrip, found 14 hours ago
$322
Roundtrip
found 14 hours ago
Mon, Jan 11 - Thu, Jan 21
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$357 Roundtrip, found 5 days ago
$357
Roundtrip
found 5 days ago
Mon, Oct 5 - Wed, Oct 21
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$366 Roundtrip, found 3 days ago
$366
Roundtrip
found 3 days ago
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