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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 $836, price is now $597 per person
$597
per person
Dec 12 - Dec 15
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 $2,874, 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
Price was $897, price is now $609 per person
$609
per person
Dec 12 - Dec 15
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 $1,932, price is now $1,344 per person
$1,344
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,970, price is now $1,395 per person
$1,395
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip 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.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $1,499, price is now $1,062 per person
$1,062
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip 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.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $863, price is now $632 per person
$632
per person
Dec 12 - Dec 15
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.

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 $897, price is now $609 per person
$609
per person
Dec 12 - Dec 15
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
Save 100% on your flight
Price was $1,172, price is now $716 per person
$716
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,932, price is now $1,344 per person
$1,344
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,970, price is now $1,395 per person
$1,395
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip 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 $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 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,881, price is now $1,228 per person
$1,228
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $3,103, price is now $2,090 per person
$2,090
per person
Dec 30 - Jan 4
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 8 hours ago
$251
Roundtrip
found 8 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 8 hours ago
American Airlines
Fri, Jan 23 - Tue, Jan 27
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$275 Roundtrip, found 8 hours ago
$275
Roundtrip
found 8 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 8 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