Cul de Sac Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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Cul de Sac Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort
Oyster Pond
Price was $1,905, price is now $1,553 per person
$1,553
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Philipsburg (SXM)
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 our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $3,473, price is now $1,958 per person
$1,958
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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
Save 100% on your flight
Price was $3,620, price is now $2,491 per person
$2,491
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Cupecoy Beach Club
Maho
Save 100% on your flight
Price was $4,785, price is now $3,746 per person
$3,746
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Philipsburg (SXM)
Stay at this 3-star beach aparthotel in Lowlands. Enjoy a beach locale, furnished balconies, and an in-room coffeemaker. Popular attractions Mullet Bay Beach and Maho Beach are located nearby.
Panorama Residences at Monte Vista
Point Blanche
Price was $2,051, price is now $1,614 per person
$1,614
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Philipsburg (SXM)
Stay at this 4-star aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
Horizon View Beach Hotel
Downtown Philipsburg
Price was $1,974, price is now $1,643 per person
$1,643
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Philipsburg (SXM)
Stay at this 3-star beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and 5 beach bars. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
Top Hotel Deals
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road, Maho Bay, Lowlands
6.15 km from city center
Stay at this 4-star beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in ...
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
4.21 km from city center
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
6.19 km from city center
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
4.25 km from city center
Stay at this 4-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 reviews. ...
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A, Simpson Bay
3.84 km from city center
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 ...
Divi Little Bay Beach Resort
Little Bay Road, Philipsburg
3.84 km from city center
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 ...
Oyster Bay Beach Resort
10 Emerald Merit Rd, Oyster Pond
5.02 km from city center
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 ...
The Atrium Beach Resort and Spa, an Ascend Collection Resort
6 Billy Folly Road, Simpson Bay
3.77 km from city center
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 ...
Hilton Vacation Club Royal Palm St. Maarten
115 Welfare Road, Simpson Bay
3.79 km from city center
Stay at this 4-star beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
Sonesta Ocean Point All Inclusive, Adults Only Resort
1A Rhine Rd., Maho Bay, Lowlands
6.13 km from city center
Stay at this 5-star 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 ...
Holland House Beach Hotel
Front Street 45, Philipsburg
3.81 km from city center
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 ...
Oceans at Divi Little Bay
Little Bay Road, Philipsburg, St. Maarten
3.4 km from city center
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 ...
Seaview Beach Hotel
#85C Front Street, Philipsburg
3.5 km from city center
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 ...
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, Mar 23 - Wed, Apr 1
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Tue, Mar 24 - Wed, Apr 1
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Sat, Dec 13 - Sat, Dec 20
LGA
LaGuardia
SXM
Princess Juliana Intl.
$317 Roundtrip, found 21 hours ago
$317
Roundtrip
found 21 hours ago
Sat, Dec 13 - Sat, Dec 20
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$337 Roundtrip, found 21 hours ago
$337
Roundtrip
found 21 hours ago
Fri, Dec 12 - Mon, Dec 22
LGA
LaGuardia
SXM
Princess Juliana Intl.
$371 Roundtrip, found 21 hours ago
$371
Roundtrip
found 21 hours ago