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Simpson Bay Vacation Packages

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Simpson Bay 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 $1,009, price is now $666 per person
$666
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $2,678, price is now $1,292 per person
$1,292
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $2,812, price is now $1,396 per person
$1,396
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $2,818, price is now $1,819 per person
$1,819
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,314, price is now $1,602 per person
$1,602
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,123, price is now $802 per person
$802
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 helpful staff in our reviews. Popular attractions Grand Case Beach and Mont Vernon are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $939, price is now $673 per person
$673
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,063, price is now $764 per person
$764
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.

Simpson Bay 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 $1,009, price is now $666 per person
$666
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,489, price is now $700 per person
$700
per person
Jul 18 - Jul 22
found 20 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,686, price is now $842 per person
$842
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,383, price is now $966 per person
$966
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

Simpson Bay Vacation Packages 5-7 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 $1,270, price is now $838 per person
$838
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $2,678, price is now $1,292 per person
$1,292
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip flight included
New York (JFK) 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 $2,234, price is now $1,097 per person
$1,097
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Save 100% on your flight
Price was $2,818, price is now $1,819 per person
$1,819
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)

Top Flight Deals

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

American Airlines
Sun, Feb 14 - Thu, Feb 18
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Feb 14 from Logan Intl. to Princess Juliana Intl., returning Thu, Feb 18, priced at $289 found 6 days ago
Spirit Airlines
Sat, May 16 - Thu, May 21
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 16 from Philadelphia Intl. to Princess Juliana Intl., returning Thu, May 21, priced at $298 found 5 days ago
American Airlines
Tue, Apr 28 - Thu, Apr 30
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$374 Roundtrip, found 6 days ago
$374
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Apr 28 from Miami Intl. to Princess Juliana Intl., returning Thu, Apr 30, priced at $374 found 6 days ago
JetBlue Airways
Sun, Sep 6 - Sun, Sep 13
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$386 Roundtrip, found 1 day ago
$386
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Sep 6 from John F. Kennedy Intl. to Princess Juliana Intl., returning Sun, Sep 13, priced at $386 found 1 day ago