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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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4 out of 5
Save 100% on your flight
Price was $1,489, price is now $913 per person
$913
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,874, price is now $1,371 per person
$1,371
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star 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 Orient Bay Beach and Maho 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 $2,052, price is now $1,140 per person
$1,140
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star 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 $1,688, price is now $988 per person
$988
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 3.5-star 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 Orient Bay Beach and Grand Case Beach are located nearby.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,652, price is now $1,190 per person
$1,190
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,784, price is now $1,287 per person
$1,287
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,303, price is now $959 per person
$959
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star 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 Beach and Grand Case Beach are located nearby.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $1,541, price is now $1,135 per person
$1,135
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 3-star beach resort in Lowlands. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Mullet Bay Beach and Maho 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
Price was $1,680, price is now $1,137 per person
$1,137
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,942, price is now $1,233 per person
$1,233
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4 out of 5
Point Blanche
Price was $1,706, price is now $1,202 per person
$1,202
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,652, price is now $1,190 per person
$1,190
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)

Simpson Bay Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,634, price is now $1,070 per person
$1,070
per person
Jan 18 - Jan 23
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 $2,052, price is now $1,140 per person
$1,140
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,830, price is now $1,188 per person
$1,188
per person
Dec 17 - Dec 22
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $2,723, price is now $1,881 per person
$1,881
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)

Top Flight Deals

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

Spirit Airlines
Wed, Jan 21 - Sat, Jan 24
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$251 Roundtrip, found 13 hours ago
$251
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Wed, Jan 21 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Sat, Jan 24, priced at $251 found 13 hours ago
American Airlines
Fri, Jan 23 - Tue, Jan 27
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$275 Roundtrip, found 13 hours ago
$275
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Fri, Jan 23 from Miami Intl. to Princess Juliana Intl., returning Tue, Jan 27, priced at $275 found 13 hours ago
Spirit Airlines
Wed, Feb 4 - Wed, Feb 11
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Philadelphia Intl. to Princess Juliana Intl., returning Wed, Feb 11, priced at $293 found 2 days ago
Delta
Tue, Jan 6 - Sat, Jan 17
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$299 Roundtrip, found 6 days ago
$299
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jan 6 from Logan Intl. to Princess Juliana Intl., returning Sat, Jan 17, priced at $299 found 6 days ago