Vacation Packages to Sint Maarten for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sint Maarten Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Oyster Bay Beach Resort
Oyster Pond
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Price was $1,105, price is now $763 per person
$763
per person
found 1 hour ago
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 Grand Case Beach and Oyster Bay Marina are located nearby.
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Price was $2,334, price is now $989 per person
$989
per person
found 1 hour ago
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.
4.0-star property
La Playa Orient Bay
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,588, price is now $1,005 per person
$1,005
per person
found 1 hour ago
Book a stay at this 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 Grand Case Beach and Green Cay are located nearby.
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,176, price is now $771 per person
$771
per person
found 1 hour ago
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 Grand Case Beach and Dawn Beach are located nearby.
4.5-star property
Panorama Residences at Monte Vista
Point Blanche
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,424, price is now $985 per person
$985
per person
found 1 hour ago
Book a stay at this luxury aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Maho Beach and Harbour Point Village are located nearby.
4.0-star property
Divi Little Bay Beach Resort
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,414, price is now $980 per person
$980
per person
found 1 hour ago
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.
4.0-star property
Esmeralda Resort
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Price was $1,311, price is now $914 per person
$914
per person
found 1 hour ago
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Grand Case Beach and Mont Vernon are located nearby.
4.0-star property
The Morgan Resort Spa Village
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,806, price is now $1,300 per person
$1,300
per person
found 1 hour ago
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. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
4.0-star property
Royal Islander Resort La Plage
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Price was $1,297, price is now $942 per person
$942
per person
found 1 hour ago
Book a stay at this beach resort in Lowlands. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Price was $1,324, price is now $974 per person
$974
per person
found 1 hour ago
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 staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
4.0-star property
Oceans at Divi Little Bay
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,535, price is now $1,130 per person
$1,130
per person
found 1 hour ago
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.
4.0-star property
Royal Islander Resort La Terrasse
Jun 7 - Jun 12
5 night stay
New York (JFK) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to New York (JFK)
American Airlines • Coach
Price was $1,149, price is now $853 per person
$853
per person
found 1 hour ago
Book a stay at this spa hotel in Lowlands. Enjoy free WiFi, a full-service spa, and a casino. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Don't see what you're looking for?
See all available trips from Chicago to Sint Maarten
View all tripsSearch vacation deals in Sint Maarten's top destinations
Simpson Bay
Top Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
6.88 km from city center
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
1 Rhine Road Lowlands
7 km from city center
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 ...
Sonesta Ocean Point All Inclusive, Adults Only Resort
1A Rhine Rd. Lowlands
7.18 km from city center
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 ...
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
4.52 km from city center
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
10 Emerald Merit Rd Oyster Pond
4.4 km from city center
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
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
4.56 km from city center
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. ...
Divi Little Bay Beach Resort
Little Bay Road Philipsburg
2.72 km from city center
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 ...
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
4.27 km from city center
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 ...
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, May 18 - Fri, May 22
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$270 Roundtrip, found 2 days ago
$270
Roundtrip
found 2 days ago
Sat, Jan 16 - Sat, Jan 23
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Sat, Jan 16 - Sat, Jan 23
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$371 Roundtrip, found 1 day ago
$371
Roundtrip
found 1 day ago
Fri, Jul 10 - Wed, Jul 15
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$404 Roundtrip, found 20 hours ago
$404
Roundtrip
found 20 hours ago
Tue, Aug 4 - Wed, Aug 5
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$405 Roundtrip, found 4 days ago
$405
Roundtrip
found 4 days ago