Deals on vacations and trips to Simpson Bay
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Simpson Bay flight + hotel vacation 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 16 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features an outdoor pool and a 24-hour gym. Families will appreciate the waterslide, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
The Villas at Simpson Bay Resort
Save 100% on your flight
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
per person
Jun 25 - Jun 30
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
La Playa Orient Bay
Save 100% on your flight
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Relax with a drink at the beach bar and enjoy free perks like English breakfast and free self parking.
Divi Little Bay Beach Resort
Save 100% on your flight
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this resort. Relax with free beach cabanas, sun loungers, and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Top Simpson Bay hotels deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
The price is $144 per night
$144
includes taxes & fees
$138 per night
May 15 - May 16
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
The price is $388 per night
$388
includes taxes & fees
$372 per night
May 4 - May 5
A full-service spa, an outdoor pool, and a restaurant are all featured at this resort. Enjoy the gym and perks like free valet parking and a free airport shuttle. There's a bar/lounge on site, and concierge services and free newspapers are also provided.
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
The price is $133 per night
$133
includes taxes & fees
$127 per night
May 11 - May 12
This resort features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and laundry facilities are also on offer.
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
The price is $173 per night
$173
includes taxes & fees
$166 per night
May 19 - May 20
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
The Atrium Beach Resort and Spa, Ascend Hotel Collection
6 Billy Folly Road, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
The price is $141 per night
$141
includes taxes & fees
$135 per night
May 14 - May 15
A full-service spa and an outdoor pool are featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A business center, a terrace, and a grocery/convenience store are also on offer.
Hilton Vacation Club Royal Palm St. Maarten
115 Welfare Road, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
The price is $169 per night
$169
includes taxes & fees
$161 per night
May 10 - May 11
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
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.
Popular places to visit
Kim Sha Beach
4/5(49 reviews)
Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and lively bars in this romantic area.
Hollywood Casino
4/5(9 reviews)
Why not roll the dice with a visit to Hollywood Casino during your visit to Simpson Bay? Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.
Simpson Bay Beach
4/5(14 reviews)
Why not spend a lazy afternoon at Simpson Bay Beach during your trip to Simpson Bay? Check out the shops and lively bars in this romantic area.
Where to stay in Simpson Bay: Best areas for travelers
- Pelican Key: If you want to experience some of this city's nightlife, make a reservation at one of the hotels in this area. Nearby options include the Beautiful Villa With Ocean Views, the Flamingo Beach Resort by Diamond Resorts and the Luxury Villa w/ Wifi, Flat Screen Satellite TV, Resort Pool, Bar & Gym. From any of these properties, you can head out and explore Hollywood Casino.
- Pelican Key: Hollywood Casino is one attraction to put on your radar here. See what it's all about and then kick back in the comfort and convenience of your nearby hotel. The Beautiful Villa With Ocean Views, the Flamingo Beach Resort by Diamond Resorts and the Luxury Villa w/ Wifi, Flat Screen Satellite TV, Resort Pool, Bar & Gym are exceptional choices.
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