Middle Region Vacation Packages for 2025
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Middle Region Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
per person
Jul 13 - Jul 19
just found
Roundtrip non-stop flight included
Oklahoma City (OKC) 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.
The Villas at Simpson Bay Resort
Save 100% on your flight
per person
Jun 22 - Jun 28
just found
Roundtrip non-stop flight included
Oklahoma City (OKC) 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 Orient Bay Beach are located nearby.
Holland House Beach Hotel
per person
Jul 13 - Jul 19
just found
Roundtrip non-stop flight included
Oklahoma City (OKC) 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.
Divi Little Bay Beach Resort
Save 100% on your flight
per person
Jul 13 - Jul 19
just found
Roundtrip non-stop flight included
Oklahoma City (OKC) 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 Maho Beach and Orient Bay Beach are located nearby.
La Playa Orient Bay
per person
Jul 13 - Jul 19
just found
Roundtrip non-stop flight included
Oklahoma City (OKC) 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.
The Morgan Resort Spa Village
per person
Jul 13 - Jul 19
just found
Roundtrip non-stop flight included
Oklahoma City (OKC) to Philipsburg (SXM)
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. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
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Sonesta Maho Beach All Inclusive Resort Casino & Spa
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
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
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
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
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
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
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
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
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
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
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
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
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 ...
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.
Mon, Jul 14 - Thu, Jul 24
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Sat, Jun 7 - Sat, Jun 14
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$331 Roundtrip, found 2 days ago
$331
Roundtrip
found 2 days ago
Sat, Aug 16 - Sat, Aug 23
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$340 Roundtrip, just found
$340
Roundtrip
just found
Sun, Jul 13 - Mon, Jul 21
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Best points of interest in Lower Prince's Quarter
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