Middle Region Vacation Packages for 2025

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Top Hotel Deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
8.48 km from Middle Region
Stay at this 4-star beach property in Lowlands. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the bar and the helpful staff in our ...
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37, Simpson Bay
6.08 km from Middle Region
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 ...
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road, Simpson Bay
8.44 km from Middle Region
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. ...
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

3.5 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
6.09 km from Middle Region
Stay at this 3.5-star 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 ...
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A, Simpson Bay
5.74 km from Middle Region
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 ...
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
1A Rhine Rd., Maho Bay, Lowlands
8.46 km from Middle Region
Stay at this 5-star luxury property in Lowlands. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our ...
JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

5 out of 5
144 Oyster Pond Resort, Building A, Oyster Pond, Sint Maarten
2.4 km from Middle Region
Stay at this 5-star luxury hotel in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Front Street 45, Philipsburg
2.55 km from Middle Region
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 ...
Fourteen at Mullet Bay

Fourteen at Mullet Bay

3.5 out of 5
2 University Drive, Cupecoy, Lowlands
9.32 km from Middle Region
Stay at this 3.5-star beach aparthotel in Lowlands. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff in our reviews. Popular ...
The Atrium Beach Resort and Spa, Ascend Hotel Collection

The Atrium Beach Resort and Spa, Ascend Hotel Collection

3 out of 5
6 Billy Folly Road, Simpson Bay
5.67 km from Middle Region
Stay at this 3-star 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 ...
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd, Oyster Pond
2.7 km from Middle Region
Stay at this 4-star 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 ...
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
147 Lowlands, Cupecoy Beach, Lowlands
9.81 km from Middle Region
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 ...
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

3.5 out of 5
115 Welfare Road, Simpson Bay
5.82 km from Middle Region
Stay at this 3.5-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
Grand Case Beach Club

Grand Case Beach Club

4 out of 5
21 Rue de Petite Plage, Grand Case
7.08 km from Middle Region
Stay at this 4-star beach hotel in Grand Case. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the restaurant and the helpful staff in our ...
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Little Bay Road, Philipsburg
3.68 km from Middle Region
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 ...
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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.

Spirit Airlines
Sat, May 24 - Fri, May 30
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$301 Roundtrip, found 21 hours ago
$301
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sat, May 24 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Fri, May 30, priced at $301 found 21 hours ago
JetBlue Airways
Mon, Jul 14 - Thu, Jul 24
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$321 Roundtrip, found 5 days ago
$321
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Jul 14 from John F. Kennedy Intl. to Princess Juliana Intl., returning Thu, Jul 24, priced at $321 found 5 days ago
Delta
Sat, Jun 7 - Sat, Jun 14
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$331 Roundtrip, found 5 days ago
$331
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jun 7 from John F. Kennedy Intl. to Princess Juliana Intl., returning Sat, Jun 14, priced at $331 found 5 days ago
American Airlines
Sat, Aug 16 - Sat, Aug 23
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Aug 16 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Sat, Aug 23, priced at $340 found 3 days ago