Search Deals onOrient Bay Vacation Packages
Orient Bay Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
La Playa Orient Bay
Price was $1,243, price is now $767 per person
$767
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orient Bay and Pinel Island are located nearby.
The Villas at Simpson Bay Resort
Price was $2,570, price is now $985 per person
$985
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 St. Martin Beaches are located nearby.
Excellent location, close to many restaurants including several on site that my family loved. We enjoyed the pool, pool bars, and the beach. Coffee shop on site, groceries, souvenirs etc. Parking was adequate. Close to airport. Felt very safe.
Reviewed on Aug 12, 2026
Simpson Bay Resort, Marina & Spa
Price was $2,073, price is now $925 per person
$925
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
You could walk to so many restaurants. All were good and food great. Only complaint some nights we had to hot water for showers. Great view and supermarket on site. Best location to go see everything
Reviewed on Aug 11, 2026
Princess Heights Luxury Boutique Condo Hotel
Save 100% on your flight
Price was $1,637, price is now $988 per person
$988
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Great Bay Beach and Orient Bay are located nearby.
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
Oyster Bay Beach Resort
Save 100% on your flight
Price was $1,396, price is now $909 per person
$909
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Great Bay Beach are located nearby.
Know how much difference the Euro 💶 and the American dollar
Reviewed on Aug 11, 2026
Sonesta Ocean Point All Inclusive, Adults Only Resort
Save 100% on your flight
Price was $3,530, price is now $2,302 per person
$2,302
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,292, price is now $848 per person
$848
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Great Bay Beach are located nearby.
Very nice facility. However the bathroom were not accommodating with hooks to hang your rib, towels or pajamas. There were no soap dish holders to hold your soap etc.
Reviewed on Aug 11, 2026
Holland House Beach Hotel
Save 100% on your flight
Price was $1,768, price is now $1,168 per person
$1,168
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Mullet Bay Beach are located nearby.
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
Orient Bay Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Orient Bay Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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