Downtown Philipsburg Vacation Packages for 2026

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Downtown Philipsburg Flight + Hotel packages

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 $1,263, price is now $711 per person
$711
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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 Pinel Island and Grand Case Beach are located nearby.

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,486, price is now $1,047 per person
$1,047
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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
Pelican Key
Price was $2,073, price is now $914 per person
$914
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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.

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,218, price is now $784 per person
$784
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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 Pinel Island 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 $1,541, price is now $998 per person
$998
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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.

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,686, price is now $1,096 per person
$1,096
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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 Mullet Bay Beach are located nearby.

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Top Hotel Deals

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Front Street 45 Philipsburg
0.86 km from Downtown Philipsburg
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 ...
Seaview Beach Hotel

Seaview Beach Hotel

3 out of 5
#85C Front Street Philipsburg
0.68 km from Downtown Philipsburg
Book a stay at this beach hotel in Philipsburg. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM

2.5 out of 5
Kruythoffsteeg#10 Philipsburg
0.78 km from Downtown Philipsburg
Book a stay at this beach aparthotel in Philipsburg. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach are ...
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Front Street, 49 Philipsburg
0.84 km from Downtown Philipsburg
Book a stay at this beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and 5 beach bars. Our guests praise the helpful staff in our reviews. Popular ...
Sea Palace

Sea Palace

3 out of 5
Front Street 147 Philipsburg
0.65 km from Downtown Philipsburg
Book a stay at this beach aparthotel in Philipsburg. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Maho Beach and Mullet Bay ...
Alicia's Inn

Alicia's Inn

2.5 out of 5
Backstreet 42 Philipsburg
0.79 km from Downtown Philipsburg
Stay at this hotel in Philipsburg. Enjoy free WiFi, concierge services, and cable TV channels. Our guests praise the helpful staff and the clean rooms in our ...
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
7.67 km from Downtown Philipsburg
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. ...
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
7.89 km from Downtown Philipsburg
Book a stay at this beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
5.08 km from Downtown Philipsburg
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 ...
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd Oyster Pond
4.3 km from Downtown Philipsburg
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 ...
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
5.09 km from Downtown Philipsburg
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
4.87 km from Downtown Philipsburg
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 ...
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Little Bay Road Philipsburg
1.84 km from Downtown Philipsburg
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 ...
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
1A Rhine Rd. Lowlands
8.04 km from Downtown Philipsburg
Book a stay at this luxury property in Lowlands. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
6 Billy Folly Road Simpson Bay
4.72 km from Downtown Philipsburg
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Nov 9 - Wed, Nov 25
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$347 Roundtrip, found 4 days ago
$347
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Nov 9 from Logan Intl. to Princess Juliana Intl., returning Wed, Nov 25, priced at $347 found 4 days ago
JetBlue Airways
Tue, Sep 1 - Fri, Sep 11
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$352 Roundtrip, found 3 days ago
$352
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 1 from John F. Kennedy Intl. to Princess Juliana Intl., returning Fri, Sep 11, priced at $352 found 3 days ago
American Airlines
Mon, Aug 24 - Wed, Sep 2
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$372 Roundtrip, found 5 days ago
$372
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Aug 24 from John F. Kennedy Intl. to Princess Juliana Intl., returning Wed, Sep 2, priced at $372 found 5 days ago
Southwest Airlines
Mon, Nov 9 - Mon, Nov 23
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$476 Roundtrip, found 5 days ago
$476
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Logan Intl. to Princess Juliana Intl., returning Mon, Nov 23, priced at $476 found 5 days ago
United
Wed, Oct 28 - Wed, Nov 11
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$480 Roundtrip, found 4 days ago
$480
Roundtrip
found 4 days ago
Select United flight, departing Wed, Oct 28 from Logan Intl. to Princess Juliana Intl., returning Wed, Nov 11, priced at $480 found 4 days ago