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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.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $1,139, price is now $827 per person
$827
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 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 $2,900, price is now $1,407 per person
$1,407
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Orient Bay 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 $2,073, price is now $1,110 per person
$1,110
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Price was $1,570, price is now $970 per person
$970
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Orient Bay Beach and Grand Case Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,451, price is now $976 per person
$976
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Orient Bay Beach and Grand Case 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 $1,943, price is now $1,328 per person
$1,328
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Orient Bay Beach are located nearby.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,425, price is now $999 per person
$999
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Orient Bay Beach are located nearby.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $1,201, price is now $893 per person
$893
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this 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 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 $922, price is now $579 per person
$579
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $2,073, price is now $1,110 per person
$1,110
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,912, price is now $1,827 per person
$1,827
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,425, price is now $999 per person
$999
per person
Mar 7 - Mar 10
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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Maho
Price was $1,066, price is now $636 per person
$636
per person
Mar 13 - Mar 18
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
Pelican Key
Price was $2,900, price is now $1,407 per person
$1,407
per person
Mar 13 - Mar 18
found 1 day 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 $1,761, price is now $1,027 per person
$1,027
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $2,438, price is now $1,525 per person
$1,525
per person
Mar 13 - Mar 18
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
Mon, Feb 16 - Tue, Feb 17
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Feb 16 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Tue, Feb 17, priced at $176 found 5 days ago
Spirit Airlines
Tue, Feb 24 - Fri, Feb 27
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$249 Roundtrip, found 2 days ago
$249
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Feb 24 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Fri, Feb 27, priced at $249 found 2 days ago
Spirit Airlines
Tue, Feb 17 - Wed, Feb 18
LGA
LaGuardia
SXM
Princess Juliana Intl.
$254 Roundtrip, found 6 days ago
$254
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Feb 17 from LaGuardia to Princess Juliana Intl., returning Wed, Feb 18, priced at $254 found 6 days ago
American Airlines
Mon, Mar 9 - Thu, Mar 12
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$274 Roundtrip, found 9 hours ago
$274
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Mon, Mar 9 from Logan Intl. to Princess Juliana Intl., returning Thu, Mar 12, priced at $274 found 9 hours ago