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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 $975, price is now $646 per person
$646
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Grand Case Beach and Dawn Beach are located nearby.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,323, price is now $728 per person
$728
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,232, price is now $699 per person
$699
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Book a stay at this beach 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 Grand Case Beach and Oyster Bay Marina are located nearby.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,718, price is now $997 per person
$997
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,614, price is now $960 per person
$960
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Grand Case Beach and Green Cay are located nearby.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,269, price is now $868 per person
$868
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,945, price is now $1,365 per person
$1,365
per person
May 1 - May 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Mullet Bay Beach are located nearby.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,130, price is now $804 per person
$804
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

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 $975, price is now $646 per person
$646
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,323, price is now $728 per person
$728
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,718, price is now $997 per person
$997
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,269, price is now $868 per person
$868
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

Oyster Pond Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,232, price is now $699 per person
$699
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,332, price is now $921 per person
$921
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,614, price is now $1,064 per person
$1,064
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $1,627, price is now $769 per person
$769
per person
May 17 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Tue, May 19 - Fri, May 29
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 19 from Logan Intl. to Princess Juliana Intl., returning Fri, May 29, priced at $292 found 2 days ago
Spirit Airlines
Sun, Apr 19 - Thu, May 7
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$299 Roundtrip, found 12 hours ago
$299
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Sun, Apr 19 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Thu, May 7, priced at $299 found 12 hours ago
United
Mon, Mar 23 - Tue, Mar 31
YYZ
Pearson Intl.
SXM
Princess Juliana Intl.
$330 Roundtrip, found 22 hours ago
$330
Roundtrip
found 22 hours ago
Select United flight, departing Mon, Mar 23 from Pearson Intl. to Princess Juliana Intl., returning Tue, Mar 31, priced at $330 found 22 hours ago
American Airlines
Wed, May 6 - Thu, May 21
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$345 Roundtrip, found 3 days ago
$345
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, May 6 from Miami Intl. to Princess Juliana Intl., returning Thu, May 21, priced at $345 found 3 days ago