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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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $1,335, price is now $952 per person
$952
per person
Dec 24 - Dec 28
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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,158, price is now $1,083 per person
$1,083
per person
Jan 5 - Jan 9
found 8 hours 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 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 $2,638, price is now $1,399 per person
$1,399
per person
Dec 24 - Dec 28
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 Maho Beach and Mullet 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 $3,396, price is now $2,148 per person
$2,148
per person
Dec 24 - Dec 28
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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,804, price is now $1,229 per person
$1,229
per person
Dec 24 - Dec 28
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.
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,551, price is now $1,752 per person
$1,752
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star 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 Orient Bay Beach and Maho Beach are located nearby.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,692, price is now $1,173 per person
$1,173
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this 4-star 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,138, price is now $1,563 per person
$1,563
per person
Dec 13 - Dec 20
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.

Simpson Bay Vacation Packages 3-4 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
Price was $2,158, price is now $1,083 per person
$1,083
per person
Jan 5 - Jan 9
found 8 hours 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 $2,638, price is now $1,399 per person
$1,399
per person
Dec 24 - Dec 28
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
Save 100% on your flight
Price was $3,396, price is now $2,148 per person
$2,148
per person
Dec 24 - Dec 28
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 $1,804, price is now $1,229 per person
$1,229
per person
Dec 24 - Dec 28
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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,610, price is now $971 per person
$971
per person
Nov 30 - Dec 5
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
Price was $2,677, price is now $1,127 per person
$1,127
per person
Jan 4 - Jan 9
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $2,833, price is now $1,667 per person
$1,667
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $3,904, price is now $2,576 per person
$2,576
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip 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.

American Airlines
Sat, Dec 13 - Sat, Dec 20
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$266 Roundtrip, found 6 days ago
$266
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Dec 13 from Logan Intl. to Princess Juliana Intl., returning Sat, Dec 20, priced at $266 found 6 days ago
JetBlue Airways
Wed, Apr 8 - Wed, Apr 15
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$289 Roundtrip, found 4 days ago
$289
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Apr 8 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Wed, Apr 15, priced at $289 found 4 days ago
Delta
Mon, Feb 2 - Sat, Feb 7
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$297 Roundtrip, found 8 hours ago
$297
Roundtrip
found 8 hours ago
Select Delta flight, departing Mon, Feb 2 from Miami Intl. to Princess Juliana Intl., returning Sat, Feb 7, priced at $297 found 8 hours ago
JetBlue Airways
Wed, Nov 12 - Sat, Nov 15
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$303 Roundtrip, found 5 days ago
$303
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Nov 12 from John F. Kennedy Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $303 found 5 days ago