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Oyster Pond Vacation Packages

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Oyster Pond Flight + Hotel Packages

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

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,060, price is now $717 per person
$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

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,893, price is now $798 per person
$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.

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,666, price is now $863 per person
$863
per person
Oct 8 - Oct 12
found 4 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

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,169, price is now $740 per person
$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

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Save 100% on your flight
Price was $2,853, price is now $1,819 per person
$1,819
per person
Oct 27 - Nov 3
found 16 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

Holland House Beach Hotel

4 out of 5
Price was $1,101, price is now $762 per person
$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

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,529, price is now $1,092 per person
$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

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Save 100% on your flight
Price was $2,043, price is now $1,462 per person
$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

Oyster Pond Vacation Packages 3-4 Night Stays

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

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $1,060, price is now $717 per person
$717
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,893, price is now $798 per person
$798
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,666, price is now $863 per person
$863
per person
Oct 8 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,169, price is now $740 per person
$740
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)

Oyster Pond Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,738, price is now $738 per person
$738
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,387, price is now $979 per person
$979
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,763, price is now $951 per person
$951
per person
Oct 27 - Nov 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,286, price is now $812 per person
$812
per person
Oct 27 - Nov 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)