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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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,495, price is now $904 per person
$904
per person
May 18 - May 26
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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $3,400, price is now $1,383 per person
$1,383
per person
May 18 - May 26
found 1 day ago
Roundtrip non-stop 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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $2,983, price is now $1,231 per person
$1,231
per person
May 18 - May 26
found 1 day ago
Roundtrip non-stop 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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,965, price is now $985 per person
$985
per person
May 18 - May 26
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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,082, price is now $1,204 per person
$1,204
per person
May 18 - May 26
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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $2,333, price is now $1,403 per person
$1,403
per person
May 18 - May 26
found 1 day ago
Roundtrip non-stop 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 $2,659, price is now $1,635 per person
$1,635
per person
May 18 - May 26
found 1 day ago
Roundtrip non-stop 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.
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,875, price is now $1,175 per person
$1,175
per person
May 18 - May 26
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Mullet Bay Beach 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
Save 100% on your flight
Price was $1,435, price is now $909 per person
$909
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $2,038, price is now $1,081 per person
$1,081
per person
Apr 15 - Apr 19
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 $1,987, price is now $1,063 per person
$1,063
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,713, price is now $1,212 per person
$1,212
per person
May 20 - May 24
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.
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 $2,133, price is now $1,023 per person
$1,023
per person
Jun 9 - Jun 14
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
Price was $2,899, price is now $1,264 per person
$1,264
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,964, price is now $1,176 per person
$1,176
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,883, price is now $1,128 per person
$1,128
per person
May 16 - May 23
found 10 hours ago
Roundtrip non-stop flight included
Columbus (CMH) 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 1 day ago
$292
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 19 from Logan Intl. to Princess Juliana Intl., returning Fri, May 29, priced at $292 found 1 day ago
Spirit Airlines
Sun, Mar 22 - Mon, Apr 6
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$300 Roundtrip, found 2 days ago
$300
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Mar 22 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Mon, Apr 6, priced at $300 found 2 days ago
American Airlines
Wed, May 6 - Thu, May 21
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$345 Roundtrip, found 2 days ago
$345
Roundtrip
found 2 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 2 days ago
Spirit Airlines
Tue, Apr 7 - Wed, Apr 8
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$396 Roundtrip, found 2 hours ago
$396
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Apr 7 from Philadelphia Intl. to Princess Juliana Intl., returning Wed, Apr 8, priced at $396 found 2 hours ago