Simpson Bay Flight + Hotel Packages

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

Princess Heights Luxury Boutique Condo Hotel

$717

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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

The Villas at Simpson Bay Resort

$798

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

The property was well kept and a good value. There are many restaurants in the area and it is close to night clubs. I did not enjoy the breakfast buffet served at the hotel. However, overall the food was good.

Reviewed on Aug 8, 2026

Simpson Bay Resort, Marina & Spa

Save 100% on your flight

$863

per person

Oct 8 - Oct 12

found 5 hours ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

La Playa Orient Bay

Save 100% on your flight

$740

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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 overall property was nice. There was mold on the ceiling from water leaking in the unit above. The shower leaks a lot of water onto the floor and the toilet rocks and needs tightened to the floor. The light above the kitchen sink only stays on a few seconds. The room was clean and overall resort was nice.

Reviewed on Aug 6, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Save 100% on your flight

$1,819

per person

Oct 27 - Nov 3

found 17 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Philipsburg (SXM)

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 in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Holland House Beach Hotel

$762

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

The Morgan Resort Spa Village

Save 100% on your flight

$1,092

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight

$1,462

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Everyone was so friendly and accommodating. My husband and I will definitely be returning!

Reviewed on Aug 8, 2026

Simpson Bay Vacation Packages 3-4 Night Stays

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